revenue summit happy hour 2018

Rainmakers were the proud hosts of a very special happy hour at The Revenue Summit Conference last week in San Francisco, California.

You can see just how proud we are here…

rainmakers team building photo

What Is The Revenue Summit?

The Revenue Summit is the only conference with a true focus on aligning sales, marketing and customer success through the lens of technology, empowering B2B leaders to accelerate full funnel growth.

This event teaches executives the most innovative and actionable best practices to scale revenue.

The Revenue Summit is a phenomenal destination for c-level enterprise leaders, as well as junior salespeople, sales managers, or demand generation marketers.

If you’re just starting out in sales, or feeling behind the learning curve, The Revenue Summit is a great place to brush up on your sales skills and learn some new things.

Rainmakers taking over the interview booth

Rainmakers taking over the interview booth!

What Companies Were There?

You can check out the full list of speakers, but here were some of our favorite companies & speakers who presented at Revenue Summit.

  • Jaimie Buss – VP of Sales (Americas), Zendesk
  • Ran Xiao – Dir. of Sales & Customer Ops, Zendesk
  • Olivia Nottebohm – Sr. Director, SMB Sales, Google Cloud
  • Laurabeth Harvey – VP of Sales, Intercom
  • Justin Shriber – VP of Marketing, LinkedIn Sales & Marketing Solutions
  • Mike Coscetta – VP of Global Sales, Square
  • Scott Brinker – VP of Platform Ecosystems, HubSpot
  • John Barrows – Leading Sales Trainer for Salesforce, Box, Marketo, LinkedIn

Why Did Rainmakers Decide To Host Happy Hour?

The Revenue Summit was such a phenomenal opportunity for us, and we couldn’t pass it up. Learn why we decided to get involved.

1. To Increase Brand Awareness

We’re still a relatively new brand that’s only been out for a few years, so we wanted to propel our visibility. Sales Hacker is a great company to partner with for that!

rainmakers revenue summit recap 2018

Mike repping the Rainmakers brand!

2. To Meet Our Customers & Prospects, IN-PERSON! 

The most underrated benefit of attending a conference, is being able to get precious face to face time with your customers and target prospects.

rainmakers booth revenue summit 2018

3. To Raffle Off Some Free Dom Perignon!

Who doesn’t love a free bottle of Dom P?

rainmakers happy hour raffle

rainmakers dom perignon rev summit

4. To Relax, Network, And Have Some Fun 

Another awesome benefit of attending conferences is the opportunity to take a load off, sip on your favorite libations, and NOT talk shop for a change.

rainmakers drinks at revenue summit

5. To Give Away Free Rainmakers Swag

Aside from the highly sought after Dom P, we gave away our signature mugs, tee shirts, and more!

rainmakers swag revenue summit 2018 

6. To Enjoy Some “Out of Office” Team Building

Company culture is very important to us, so this was a great opportunity to get out of the office and do a little off-site team building.

company team building revenue summit 2018

Top Sessions & Key Takeaways From Revenue Summit

The Revenue Summit features keynotes from industry-leading sales practitioners to deliver educational and actionable content across two tracks (strategic and tactical).

Here’s a recap from Morgan J Ingram that nicely summarizes the key takeaways for the day!

9 Elements of Highly Effective Sales Conversations — Amit Bendov, CEO, Gong

How To Generate Leads on Auto Pilot — Eric Siu, CEO, Single Grain

Full Funnel Forecasting — Zendesk, Sales Leadership Team

How To Build A Viral Marketing Funnel — Olof Mathe, CEO, Mixmax

How To Prospect Using The Basics — Ralph Barsi

tech sales job opportunities

Why Tech Sales Jobs Are The Best

If you’re currently exploring your job options, have you considered a tech sales career?

If not, there are several reasons why you should consider joining the ranks at a software or technology company and using your skills to help them continue to grow and make an impact.

Why? Here’s everything you need to know about why a tech sales career is worth considering.

What is Tech Sales Anyway?

In a tech sales position, you’ll be responsible for connecting consumers (individuals or other businesses) with technology that can help them solve a specific problem.

Exactly what type of tech you’re selling—from actual hardware to software or other services—will vary depending on the kind of company you work for.

But, regardless of the specifics, in this customer-facing role, the critical thing to know is that you’re tasked with connecting with and educating potential customers—and ultimately closing the deal.

For some added clarity, you should check what Ralph Barsi wrote about SDR job descriptions and what they’re REALLY telling you.

Tech Sales Job Description Example:

Here’s a look at a tech sales job description example. Below is a posting for a Sales Development Representative role with Wrike, a project management software solution:

sales job description

6 Reasons to Consider a Tech Sales Career

We know your next question: Why even start a career in tech sales? Well, plenty of benefits make this a particularly appealing career path. Here are four to consider.

1. The Demand is High

Considering that sales are quite literally what keeps every company’s doors open, it makes sense that there’s a lot of security and demand in this career field.

But, as technology continues to become even more prevalent in our day-to-day lives, tech companies, in particular, are aggressively adding people to their teams who can get their solutions and products in front of a wider audience.

A recent study from ToutApp—which surveyed 300 HR managers at U.S.-based technology companies with at least 200 employees—found that 80% of respondents stated that they intend to invest more in recruiting and hiring sales talent.

While others may worry about things like automation or online capabilities replacing the need for their jobs, that’s not the case for sales—where human interaction still carries a lot of importance.

Research from the Harvard Business Review found that direct interactions with providers influence B2B purchasing decisions more than anything else. Demand for tech sales professionals is high (and will likely stay that way). So, it’s an incredibly secure and lucrative path to pursue.

b2b marketing

2. The Pay is Great

Speaking of lucrative, the salary is another big draw for many tech sales professionals. While the tech industry is known to pay hefty sums to the people who fill the more technical roles, you can also earn a great living in sales.

Bridge Group’s 2015 SaaS Inside Sales Survey Report shared that the compensation for inside sales roles rose to record highs in 2015.

The company discovered an average base salary of $60,000 with average on-target earnings of $118,000—proving that technical roles aren’t the only ones who earn the big bucks.

While a paycheck isn’t everything regarding your job satisfaction, knowing that a career path in tech sales quite literally pays off makes it worth considering.

3. The Career Opportunities Are Seemingly Endless

Nobody wants to reach a limit on their career, which is another thing that makes tech sales so appealing: There are seemingly limitless opportunities for growth and advancement.

Many tech leaders got their start in sales—because it’s a great way to gain familiarity with the business and customers while also making a measurable impact on the organization’s success (you need revenue!).

So, as you gain more experience, continue to close deals, and prove your worth, you’ll likely experience rapid progression in your career.

Take a look at LinkedIn’s data as an example. LinkedIn pulled together a list of the most promising jobs of 2017—the ones with the highest median salaries, strong job openings, and year-over-year growth.

Which job appeared third on that list? A sales engineer proves that pursuing a career in tech sales could mean bright things for your future.

why sales jobs are great

4. The Barrier to Entry is Low

The tech industry can be intimidating and leave many wondering how to get into software sales without experience.

Fortunately, this is another upside of a career in tech sales: There’s a shallow barrier to entry.

“There’s often no formal education and training programs for sales pros; it’s something many people discover as a career by accident,” explains Sharon Florentine.

This means these roles are challenging for recruiters to hire—but it also means that people with diverse backgrounds and experiences can make a name for themselves in sales positions.

There’s no strict mold you need to fit into or overly formal criteria you need to meet to find success as a tech sales professional.

5. Career Security

We all know tech is the future (and the end is now). Hence, as time progresses, technological solutions may take more “traditional” jobs that will not surprisingly need salespeople to sell them.

Unlike many other industries at the whim of a physical good’s supply and demand cycle, technology, specifically tech sales, are often roles that can be done with little resources and even remotely if needed.

Both technology and sales are never going away, so if you are worried about your current industry’s longevity, you won’t need to worry so much about tech.

contact rainmakers

6. It’s Exciting Work

Having a job that pays well is one thing, but having a job that interests and stimulates you mentally is another. In the world of tech sales, there are endless opportunities to find niches that work for you, your interests, and your passions.

You often get to help others solve their problems using a unique solution you have to offer, and in learning about your product, you may even find ways to improve it. So if you are going to start fresh looking into a job in tech sales, start looking in the industries that you are personally interested in to help fuel that inner fire of excitement and motivation.

Ready to Get Started?

Now for the final question: How do you get started? Create a profile on Rainmakers, a career marketplace explicitly designed for salespeople.

Use your profile to highlight your skills, share your history, and prove your value to inspire interested employers to contact you. You’ll be well on your way to a tech sales career in no time!

best time to find new sales job

Is It Time To Move On?

Should I quit my sales job? This is a question all sales professionals ask themselves at some point in their careers.

This is a guide on when it’s time to leave your current sales job and look for a new one. This guide is written specifically for SaaS and other technology sales reps who work at venture-funded companies, but it can be applied to different verticals.

Working in B2B sales is hard. If you’re at a small company where generating new revenue means keeping the lights on, the company’s existence depends on your performance. That’s a lot of pressure. Likewise, at a medium-sized or large company, being in sales means constant competition with the entirety of your team for a limited amount of available promotions. That’s also a lot of pressure.

But sales, with its clear-cut metrics, is an excellent way for career-driven individuals to prove themself in the workforce. Not to mention salespeople in Silicon Valley often make six figures within three years of graduating. Oracle’s highest-performing sales reps make over $500,000 a year. Being good at sales will help your career, but knowing when to change jobs strategically will allow your sales insight to deliver the highest return.

First, we’ll go over the main paths of ‘success’ a sales career can take. Then, based on which of these paths you find most appealing, we’ll help you identify whether or not your current job is an opportunity worth staying at.

 quit your sales job

The 3 Sales Career Paths

According to Mark Roberge, professor at Harvard and CRO of HubSpot, here are three typical paths a sales career can take:

1) Moving into sales management.

This is an excellent path for people who are passionate about leadership, teamwork, and strategy and like to see the big picture. Sales leaders at medium and large-sized technology companies are always richly compensated.

2) Remaining as an individual contributor, working on larger and more complex deals.

This is an excellent path for people who enjoy independence and competition and appreciate the detail. For example, salespeople in the top 20% at SaaS and technology companies typically earn between $250,000-$500,000 a year.

3) Moving horizontally into marketing or customer success.

This path is for people who use sales as a short-term or medium-term stepping stone. For example, many successful marketing and customer success executives began their careers in sales.

This guide will focus on the first two paths and show you some signs to help you determine when it’s time to leave your current role.

Individual Contributor Path

If your goal is closing the largest and most complex deals possible, changing jobs from time to time is almost a necessity. This is especially true if you begin your career working at startups (as opposed to somewhere like Oracle or SAP). Two primary factors determine the size and complexity of a deal — the size of the company with whom you are doing business and the complexity of the technology you are selling. Let’s further review sales career pathing via the lens of this growth chart, courtesy of our friends at InsightSquared.

sales career path ideal candidate

Most SaaS salespeople begin their career in the bottom left of this graph, selling relatively simple software to small and medium-sized businesses. However, at the top row of this graph, you have Silicon Valley’s highest-paid salespeople, selling complex technology to large institutions, a.k.a. enterprise salespeople. This is where you want to get with your career as soon as possible.

Thus there are two directions you have to move. You have to move up from SMB to Mid Market to Enterprise. And you have to move towards the right, towards more complex technology. Using this paradigm, it becomes relatively easy to determine when you should leave your sales job.

How to know when it’s time to quit your sales job

  • Your company doesn’t sell to MM or Enterprise accounts; you’ve been a top 20% performer for 9-15 months and have nowhere higher to go.
  • Your company isn’t growing fast enough to promote salespeople to higher brackets.

Concerning selling more advanced technologies:

  • Once you’ve made it to Enterprise sales, if you’re company is selling a simple, easy-to-sell product, the next move should be towards a company with a more expensive and difficult-to-sell product (thus a higher commission)

If you love your job and don’t want to leave, there’s no need to. However, if your goal is to maximize your revenue as quickly as possible, using the above criterion to determine when to leave a job can be very helpful.

The best option is to leave for a promotion (i.e., leaving a mid-market sales role for an enterprise sales role).

If this isn’t possible, a significant next step would be to leave for another company growing fast enough to support your growth.

When doing this, it’s essential to understand your new employer’s expectations, i.e., what must be done to secure a promotion. If possible, secure an agreement in writing (if I achieve X metrics in Y amount of time, I am awarded Z promotion). Note that this is often only possible with early-stage startups and more difficult to broach with a developed company.

Sales Management Path

If you’re passionate about leading a sales team, one major thing you have to look for in a company is growth.

If a company’s sales team triples in size, it will have to hire managers to help keep things in order. If your company’s sales team isn’t growing, there’s no need for them to hire more managers, and you should look elsewhere to further your career.

There are three types of companies that can move you into management:

Large, stable-sized companies.

They aren’t growing rapidly, but every once in a while, someone retires, is fired, or leaves. These promotions take a long time to achieve.

Medium-sized, rapidly growing companies.

Some contemporary examples are Flexport and Mulesoft. These companies already have senior management in place, but teams are growing so fast that regional leaders are often promoted from the rank and file of sales reps.

Small startups with high potential.

Often, an early Account Executive of a small startup will have an opportunity to lead the sales team if significant growth happens.

If you’re looking to move into sales management, you first need to evaluate if you’re in one of the three above situations in your current role. If you’re not, it’s time to find a new job.

If you are in one of the above situations in your current role, you’ll need to gauge the likelihood of securing a promotion. Here are some things that will help you evaluate your changes:

If the answer to the above questions is yes, then you have a relatively good chance of securing a move into management. Now it’s worth engaging with your boss to see where they stand and let them know it’s a priority for you.

If the answer to one (or both) of the above questions is no, on the other hand, you likely won’t move into management at your company. So at this point, it may be worth looking for other opportunities where you’ll be more likely to succeed.


Other reasons to leave your sales job

Ideally, we leave our sales job strategically to advance our careers. However, sometimes you’re stuck in a bad situation, and it’s worth going regardless. Here are some reasons we think salespeople should leave their jobs:

Poor management:

This can be anything from an ineffective sales strategy to unfair personal treatment. If your boss or CEO prevents you from doing your job well, it’s most likely not worth sticking around for.

Company doesn’t value salespeople:

Low-paying commission plans, unrealistic quotas that no one hits, and not taking salespeople’s feedback are all signs that your company doesn’t value salespeople. Therefore, it’s better to work for a company that does.

You don’t believe in the product:

If market adoption of your product is slumping or your company is failing to improve the product continuously, it’s time to look for a new role. As a salesperson, you only want to sell the best products — selling a product you don’t believe in is soul-sucking.

contact rainmakers


Navigating your career through Silicon Valley’s sales world can be daunting. With so many companies being born, rising, falling, and stagnating. It’s essential to evaluate how your employer’s interests align with yours constantly. You’ll have an incredible career if you can consistently perform well at solid and growing startups. Transitioning companies at the right time is a skill that’s necessary for salespeople to be in front of those career-changing opportunities.

Too often, people leave their company without a clear goal; worse, they make their decisions emotionally rather than logically. Consider this guide a piece of empirical-based advice to refer to when comparing your current situation with the situations described above. Use it to know when it’s time to leave your job so you can constantly maximize the return of your talent and hard work. Then, please find the job that will get you where you want to be.

Are you ready to quit your job and start a new career? Apply now with Rainmakers and start looking at new opportunities!

how to negotiate a salary increase in your job

Negotiating a salary raise can be tough, even for the most experienced negotiators. In this article, we’ll break down how to do this in the context of sales, but the principles of negotiation can be applied to any role or industry.

Let’s face it, we all want more money in our job, but very few people (if anyone) enjoy the negotiating process.

Just thinking about it makes even the most seasoned pro break out in sweat. However, it need not be this way. By preparing ahead of time, you have a much better chance of achieving your negotiating goals.

A key point to consider: research says salespeople who negotiate earn 7k more on average each year than their counterparts who do not. Over a career, this can add up to nearly a quarter of a million dollars.

The trick to any successful negotiation is to be prepared, so roll up your sleeves and get ready to negotiate.

6 Things To Do BEFORE The Salary Negotiation

  1. Research is key. Know more than your boss about every aspect of your career. How much would it cost to replace you? What do others make in similar industries?
  2. Visualize the encounter- what are the objections? Write them down and have a researched answer for each one.
  3. Reach out to recruiters in your field and find out what your contemporaries are paid. Ask them for advice in the negotiating process. These are people who negotiate every day.
  4. First, by yourself in front of a mirror. Watch to make sure your body and face look calm. Remember to breathe and smile, even when you receive bad news. Make good eye contact, but do break away, and look out the window for seconds at a time. This will allow your boss to relax and really hear you.
  5. Practice closer to the real date with a close friend. Get feedback on your body language and your verbal pitch.
  6. Prepare visual content that speaks to your point. We are visual creatures, and you want to speak quickly and effectively to your points.

20 Steps To Follow DURING The Salary Negotiation

  1. Try owning the space you negotiate in, i.e., taking your boss to a new restaurant, one that you know well. This is a time to impress. You might even order for the both of you. You are showing your “take charge” nature, something that is a winner in sales.
  2. Listen more than you talk in the meeting. Show the skills that make you an amazing salesperson. Repeat your boss’s points back to him to let you know you hear him.
  3. Know the whole picture, base salary, commission, vacation days, upward mobility track, 401K etc. Be able to discuss with research where your current job fits within the industry standard.
  4. Be able to prove how valuable you are: numbers, culture, training, etc. These need to be in either spreadsheet or graph form, big enough that your boss can see it at a glance. Paint the entire picture — if you bring donuts on Tuesday, remind them.
  5. Show the problems the company is facing in the coming years, and how you will help.
  6. Resist the urge to badmouth your fellow workers. Take the high road and be above the petty office gossip.
  7. Come with urgency, you don’t want a raise down the road, or “one day” You want it now!
  8. Imply that recruiters have reached out to you, but that you are loyal. “I know that loyalty is important to you.” You don’t need to lie but be able to prove with evidence how recruiters are looking for people with your skill level.
  9. Use silence, if your boss says no, nod your head, you hear it, but then be silent. He who speaks first loses.
  10. Be prepared to talk about your successes and try to use that as leverage. For example, if you have a strong personal brand, explain how you might leverage that in your sales process.
  11. Try being creative, “What if you paid me more for 3 months, and if I didn’t make my numbers, I would go back to my old salary? “Remember this is a negotiation, where ideas are passed back and forth. Don’t accept any answer, but keep the information flowing.
  12. Try laughing, keeping the meeting light, remind the boss of good times. A lighthearted worker is valuable for the energy they bring to an office.
  13. Agree as much as possible, when you disagree, say things like, “I see what you are saying there, but…” You are showing your ability to listen and have your own ideas.
  14. Ask where you fall in the scale of salespeople? Or know it, what would be the effect of you leaving?
  15. Know the industry: Where are the struggles? Where is the growth? Who are the big players? Who is the competition?
  16. Be prepared to give as well as take. If they can’t meet your salary, can they give you higher stock options? Could you telecommute 1 or 2 days a week?
  17. Could you train new salespeople for an additional bonus?
  18. Don’t be afraid to bring some personal information into the meeting, talk about your plans for building a house, or moving your mom to live with you. These make you look like more than just a worker.
  19. Show how you could grow into management, how you could help the boss retire early. Or work less.
  20. If you have made mistakes, missed quota, or had other office problems, be the one to bring them up. Show how you have grown as a result.

4 Things To Do AFTER The Salary Negotiation

  1. Pick up the check, this can go miles in proving how generous you are. When your boss objects, say “You can always grab the next one.”
  2. Be prepared to be watched like a hawk the next few days as your boss thinks about what was discussed. Let your work reflect your words.
  3. Write a thank you letter to your boss for meeting with you. Cover the main points that were discussed, and what, if any, agreements that you came to.
  4. Be prepared for the idea that it may take more than one meeting to get your raise. Be in for the long game.

By learning to negotiate we can get more of what we really want in life. Most people give in too easy here, and we let others dictate what we get.

However, the master negotiator doesn’t, and as a result they make more money and are more satisfied in their sales careers.

Learn to negotiate and win.

should i tell my boss I'm looking for a new job?

Should you tell your boss you’re looking for a new job? This article is explained in the context of sales, but it can be applied to any profession. Let’s dig in.

Opportunities seem to be everywhere. Your friends and colleagues are leveling up, and you’re starting to feel like it’s YOUR time to do the same.

One question always arises: should you tell your current employer or boss that you’re looking for a new position?

Let’s look at the Pros & Cons of both sides of the question…

Your current boss is actually a close friend.


Is your relationship with your boss good? Can it handle something like this? Oftentimes we have developed deep positive relationships with our boss. He/she has trained us, gone to bat for us when things are wrong, and been a mentor for our careers. It would feel like betrayal to go behind his/her back.


Mary would have never started her Real Estate Sales career without the assistance of her boss, Mark, who recognized aspects of her personality that he thought were “sales” material. The thought of even talking with a recruiter seemed like plunging a knife into Mark’s back.


Your network is everything, but you don’t want this to damage the relationship. Your boss is nice to you, but that’s how she acts to everyone who works there. Be mindful, however, that this doesn’t mean you need to tell her everything.


Richard really enjoyed working closely with his boss, Nick, and they even enjoyed a relationship outside of work. Three years into the position, Richard became bored and jumped on a new opportunity when it came along. There was a point at which he thought about telling Nick, but since there was no other position in the company that could reignite his interest, Richard gave his two weeks with little explanation. Three years later, he has no regrets and even sees Nick as a friend.

Your boss might be an ally and help you find something that fits.

It costs so much time and money to hire and train a new employee, so your boss will be grateful if you are honest.

He/she may even help you find something at your current business that is more in line with what you’re seeking.

So many people just quit, so you will appear different and unique by doing sharing your needs in respectful way.

Even if you are fired, you will come out looking better for your honesty. You won’t use the company’s time or resources to look for new opportunity.


Your boss will respect your honesty and reward it.


Danny was an excellent AE. He hit his sales quota every month, but his work was unfulfilling.

He constantly watched the clock and dreaded each Monday. When he unexpectedly got a chance to train the new hires, Danny was excited about work for the first time.

He approached his boss, whom he considered a close ally, with a plan to split his day into part AE/part sales trainer.

His boss, who was initially reluctant, realized that Danny was not fulfilled and if he didn’t give him this opportunity, he would leave to find it elsewhere.


If you stay in the same field, you are in direct competition with your old company. Going head-to-head with the people who gave you a start in a particular field is troubling.


Linda wouldn’t even be in this line of work, had her boss, Tammy, not seen something in her and pushed her hard. She was on the bottom rankings for months, but Tammy still believed in her. When the recruiter reached out, Linda was flattered but made it clear that she would never go head-to-head with Tammy’s company. She eventually found another line of work she liked better that didn’t conflict with her loyalty.

It’s not about the job, it’s about the culture.

Sometimes our desire to leave has nothing to do with the boss. Rather, it’s a toxic company culture that is pushing us to go. It might be the line of work itself or our fellow workers. Whatever the cause, work is no longer fulfilling. We just aren’t enjoying work, so we know we need a change.


We can’t change company culture. We can either adapt or leave.


When Pete first started at Company XYZ, he loved the loud sales floor and all of the chaos that was his job. As time went on, this kind of work drained him.

After visiting his friend’s job, where the sales floor was silent, that seemed like a better fit for him. He thought about approaching his current boss about a shift in his position; however, there was not a position that wasn’t directly involved with the loud floor except for accounting. Pete knew he would have to leave.

As nice as his boss was, Pete knew that his boss thought this was the only way to run a sales floor. He had trained this way, run his floor the very same way, and was resistant to any changes. Pete applied for the new job and left his current position without any guilt. He is two years into his new position, which he loves.


Company culture is something we learn to adapt to, and it’s a chance for growth.


Nora was always the quiet one, so FinTech was a hard place for her initially — especially with a loud sales floor and a bell that rang after each sale. She thought about quitting, but the pay was too good. After a few months of ringing that bell herself, something shifted inside of her, and now Nora is an A-Player that loves the loud atmosphere and has fully embraced the ruckus attitude.

Some people don’t handle this kind of rejection well.

Your “secrecy” might be your best weapon. Some people feel their current boss hasn’t earned their loyalty or the right to know the “truth” about the way they feel about their job.

Has your current boss earned the “truth”? Perhaps the company culture is such that even a new position with the current company will not be satisfactory.


You would tell the boss you are dissatisfied and looking for something new, but they will just punish you for honesty.


Laura had seen her boss not handle job dissatisfaction in her coworker very well. “Don’t let the door hit you in the backside,” was a constant refrain. He was the kind of boss who you were either with or against. Laura had been dissatisfied for a year now, but there was never anything better on the horizon. When a new job opportunity materialized unexpectedly, she naturally jumped on it.


Even if the boss yells and doesn’t handle it well, you have to be honest.


Clint wanted to move up to AE from his current SDR position, but he knew that his boss would just tell him it was too early. When the recruiter called and sent him the AE job offer, Clint confidently showed his boss. Fireworks and slammed doors ensued, but Clint knew that his boss knew that Clint would one day be an AE.

Honesty won’t work because the boss can’t hear you.

It has been said that running a business is like attending to a screaming baby. Your career is more than your job; it is your livelihood. A good boss can see you beyond your current position.  She can see where you need to be.


They say telling the truth to someone who can’t hear it is like telling them a lie.


Mark loved his boss, but every time he approached her about moving up, or learning new skills, she waved him away saying, “You are my best SDR.” Mark believed her, but the thought of being an SDR in two years made him sick to his stomach. He knew he could, and would, make an excellent AE. When a recruiter finally approached him, Mark scheduled a sick day to meet. “I got the job, and quit with no notice and no regrets,” he remembers, “This is not just a job; this is my career.”


You would like to be able to use this job as reference, but if you just quit, that will never happen.


Jen was stuck in her sales job, never in the top rankings, but never in the bottom. She knew just leaving would mean that her dream of working for X Company would never happen. She decided to stay and push harder for high rankings. It took several years, but she proud of her decision to stick it out.

Conclusion: Should You Tell Your Boss You’re Looking For A New Job?

It is a moral and personal decision whether to tell the boss you are looking for a new job. Some people will have regrets while others have none. Either way, it is a decision we make and then live with for the better – or worse – of our careers.

business networking tips

For a good reason, networking for sales professionals has long been considered sage advice. This best practice can open up many doors for you, whether in friendships, mentorships, new career opportunities, and even earning referral sales opportunities.

But What Exactly Is Networking? (And How Should You Go About It?)

To network is to cultivate people around you who can help you professionally. This may come naturally to some, but for most, and especially for those who are more introverted, the task can seem much more daunting than it is appealing.

Becoming proficient at networking is synonymous with mastering the art of making friends. At the end of the day, we’re all human beings and, as such, tend to want to help one another. This is a more accurate sentiment when those who need help are befriended.

However, this is much easier said than done. To walk into a room full of strangers, confidently present yourself and quickly find relatable topics of conversation to build relationships is no easy task. After all, it’s not like we’re mind readers.

Here are a few tips you can lean on to help make the whole process of transitioning from strangers to friends a more welcoming ordeal.

how to succeed at networking

Step 1: Prepare A Personal Pitch

The first thing you’ll want to do to get ready for a networking event is to prepare a personal pitch. Your personal pitch is a short but exemplary description of who you are and what you do.

After all, the question you’ll probably have to answer the most at any networking event is, “Who are you? And what do you do?”

Having a quick answer to these questions that is easy to comprehend is key to helping keep your interactions smooth. Stumbling through trying to explain who you are can come off as unconfident and leave a wrong initial impression.

Part of your pitch will be driven by your event goal, which is a perfect segue to our next piece of advice.

Step 2: Have A Goal In Mind

Networking, like many other life endeavors, can prove ineffective without a clear objective in mind. When approaching a networking event, try and think to yourself what it is you’d like to get out of it. Are you trying to find a mentor? Are you looking for prospects to drive future sales? Or are you simply trying to meet more people in a particular field? Having a specific goal in mind will help frame your interactions and conversations.

Let your goal be your mission, let that mission drive you, and let that be clear. Then, just as you understand who the people you meet are and what they’re doing, they’ll also begin to know what you’re looking to accomplish. Even if the person you’re talking to at that moment isn’t directly relevant to your goal, they may have just met someone or know someone in their network that can help you get to where you want to be.

how to network like a pro

Step 3: Have A Few Ice-breakers Prepared Ahead Of Time

Even the most socially adept people in the world are bound to have a few harmful interactions. Simply put, it’s impossible to be on top of your game 100% of the time. Maybe you’re drained from a long day at work, or perhaps something is pressing that suddenly pops into your mind at the wrong moment. Whatever the case, it’s very easy for us to become mentally distracted; for some, it only makes finding a conversation starter that much more difficult.

As such, to avoid that mental stress and save your energy for keeping engaged with the ongoing conversations, it’s a good idea to have some ice-breakers saved in your back pocket. That way, you can fall back on them without much thinking and get people talking quickly.

The rules of topics to avoid in the workplace also apply here. For example, you don’t want to argue with someone you’ve just met with if you’re trying to win their favor. That means you generally want to avoid talking about politics, religion, personal gossip, death, or the myriad of other topics that may be controversial.

If your mind is running blank, here are a few suggestions to get you started:

  • Recent sporting events.
  • Plans for the weekend.
  • Reasons for attending the event.
  • Advice on small challenges that you’re facing personally or at work.
  • Listen intently.

It’s relatively easy for people to tell whether or not someone is genuinely listening to them. I’m sure we’ve all been guilty of this at some point, where we nod as someone is talking just to let them get out what they need to say, but we’re mentally checked out somewhere else. On the flip side, I’m sure we’ve been on the receiving end of this behavior at some point as well.

The moment someone realizes that you’re mentally checked out of the conversation, they’ll stop caring about you. Why? They probably feel you don’t care about them. So why should they take an interest in someone who isn’t reciprocating? Needless to say, it’s no way to make a good impression.

When someone is fully engaged in a conversation, there will be tell-tale signs that the person has been paying attention. Outside of body language, such as facing their direction and nodding your head, a good listener will occasionally rephrase parts of what they’re hearing and offer their thoughts on specific points. In addition, if you can relate some of the later topics of conversation to things mentioned earlier in the engagement, you’ll probably land a few bonus points there too.

best networking tips for sales pros

Step 4: Bring A Friend

In fact, bring a few. Going to networking events as a group can offer several benefits over going alone. For one, as a group, you’ll be able to cover more ground because you guys have come as a unit. This inherently means that the group already understands each other’s objectives, increasing the chances that at least one of you will find the right person to connect with.

Secondly, you can leverage each other as a social crutch. For example, sticking together as a pack may draw others to grow your cluster and start conversations quickly. Additionally, because your group of friends is already familiar with one another, the rapport building amongst the group will probably feel more natural and suave, creating a comfortable environment for others to join.

Furthermore, interacting with strangers for an extended period can definitely prove to be a mentally draining activity. Therefore, if you need to take a break from all the action, you can rendezvous with your friends for some momentary relief.

Of course, there are many other things you could try to work on to improve your chances of making a great first impression, such as paying attention to the tonality of your voice and being conscious of your body language.

Why? Because we must emphasize how important it is to be aware of how we come across to other people when we first meet them. Your tonality and body language are some of the easiest things you can focus on if you’d like to get better at making an excellent first impression.

Just as you can use words to convey different meanings to compel people to feel specific ways, you can also use your body for that exact purpose. Through his research in 1971, Professor Mehrabian famously discovered the 7% rule, which is to say that words only contribute 7% to the importance of what is being conveyed. The other 93% comprises nonverbal elements such as body language and tonality; body language takes the lion’s share of that, with 55% and tonality accounting for the other 38%.

Step 5: Make Good, Solid Eye Contact

Working on eye contact is a quick and easy way to improve your body language. Though it may feel awkward for some, making eye contact is a great way to build rapport with someone you’ve just met quickly. Good eye contact conveys to the speaker that you are paying attention and are genuinely interested in what they have to say.

If you are one of those people who find making eye contact awkward or unnatural, as a general rule of thumb, where you want to be looking is the triangular area of a person’s face where their eyes and mouth act as the corners of that triangle. You also want to make sure that you’re breaking eye contact naturally with the flow of the conversation from time to time because otherwise, you might just come off as really creepy. You can even try focusing on one eye at a time and alternate between the two to see if it helps make things feel a bit less awkward.

master networking

Step 6: Practice Nodding Where Applicable

Another quick nonverbal tip that can win you some easy points is nodding as someone speaks. Just like eye contact, nodding indicates to the speaker that you understand what they are saying. This is somewhat of a mind trick, and feel free to test this out, but when someone starts nearing the end of what they intended to say, and you want to hear more, nod your head three times. This encourages them to elaborate further, which people often do.

Step 7: Remain Aware Of Your Body Orientation

Something else you might want to pay attention to is how you orient your body. For example, you generally want to be positioned so that your chest is facing the person you’re speaking to in a one-on-one engagement or towards the center of the group when in a group setting.

Even if you’re head is facing toward the individual you’re speaking to, if your torso is facing elsewhere, that person will get the sense that you are not giving them your full attention.

Slightly more advanced is ensuring that your feet are correctly oriented. Again, you want your feet to generally point in the direction of the person you are speaking to or towards the center of the group in a group context. Feet can say a lot about people’s intentions. When someone is about to leave a conversation, you can often tell because their feet will turn in the direction they intend to go before the rest of their body.

Step 8: Keep a Good Posture

Confidence is a massive part of making a good impression. When people congregate together in a room, it’s not the coy individuals on the side that everyone notices. No. The confident individuals in the center of the room catch people’s attention.

A good posture is one of the best ways to convey confidence. That means keeping your back straight and chin up. If you’re someone who happens to slouch often, trying to fix your posture can understandably feel awkward. Furthermore, some people may find even overcorrecting and strain their backs in a forced effort to keep it straight. You definitely want to use your back muscles to support your weight but not to the point where you feel uncomfortable when holding your form.

Also, keeping your chin high means not tucking in your chin too often. Someone constantly looking at the floor or otherwise in a downward direction comes off to others as shy and unconfident, which is the exact opposite of the message you want to send. This also shouldn’t be overdone to the point where you’re looking down on people, but it is something that you’ll want to pay closer attention to.

great networking tips

Step 9: Use Reciprocal Tonality

It’s not likely that this is a term you’ll find being used elsewhere, but the idea represents the use of tone to respond appropriately to what is being said. For example, if someone just told you about a fantastic weekend they had, it would be an excellent opportunity for you to add some excitement to your voice. This lets the speaker know they’re doing a fantastic job sharing their experience and makes them feel better being listened to.

Getting this wrong could significantly hurt your chances of making an excellent first impression. Not that I’d imagine anyone to do this, but if someone were to tell you they were ill, a proper response would not be to respond with, “Hey, that’s great!” Failing to respond appropriately could lead to a very awkward situation, so be mindful of how you respond.

Step 10: Have A Strong Voice

Again the goal in your interactions should be to come off as being confident. In addition to having good posture, another way to demonstrate that you are indeed a confident individual is to have a strong voice. As with all of the advice thus far, moderation is key.

You want to be loud enough to easily be heard by those you are speaking to but not so loud that you’re basically screaming at people. On the other hand, being too loud or soft in your speech can irritate some people. No one likes to be yelled at, and there’s nothing more frustrating than putting in more effort to try and make out what someone is saying.

Follow the Goldilocks Principle and find that perfect medium that will pave the path for you to sound like a complete rockstar.

sales recruiters

Step 11: Use Hand Gestures Thoughtfully

Lastly, using your hands can be a great way to help make a lasting impression. Using your hands will allow you to be much more expressive in communicating your thoughts and enable others to remember what you’re saying more easily.

When using your hands to communicate, you want your gestures to match what’s being said. For example, when describing something small, a pinching gesture could do well to accompany your message.

Gesturing also helps you convey a sense of enthusiasm and confidence, which is precisely what you want to do when trying to network.

So, as a quick recap, you want to pay attention to eye contact, nods, posture, tone, volume, and hands. It may be a bit much to try and improve on all of these areas all at once, so I recommend focusing on just 1 or 2 at a time. Then, once you feel well-mastered in one place, move on to the next until you become a networking virtuoso.

Need help growing your network and connecting with potential employers? Join Rainmakers now!

why get a new sales job

Should You Change Jobs?

Here’s a complete list of pros and cons to consider when thinking of making a switch. ​​

Look on any LinkedIn Jobs Posting, and it becomes apparent that it is a buyer’s market in the Tech SDR and AE talent pool. More sales jobs are available than at any other time in our history and with good reason. A top-notch AE can be a rainmaker for a company bringing in millions to the bottom line.

SDRs only have a market life of 18 months, but a skilled Sales Development Rep sets up an AE with solid leads to close, and this is an invaluable skill in our modern business climate. With a new tech company popping up with funding every week and savvy recruiters prowling LinkedIn’s rich waters, chances are if you are a good salesperson, someone will make you an offer too good to refuse. We need to look at the pros and cons of a job offer.

However, does it make sense to change? Change is good, but with any job change, you need to look at the new vs. old job with a critical eye. Try to make a pros and cons list of a job offer outlining everything that needs the critical eye before the jump.

Perceived PRO: Earning Potential = More Money

Perceived CON: Not As Much Income Security

Did you find a better job, or does it just look better?

Where does it fall in the job change decision matrix?

Are the benefits, the work environment, and the income potential all aligned?

Salespeople sell and are sold to. This means we buy easier than the average person.

That sales manager who’s talking to you… he sells for a living, and right now, he is trying to sell you this job.

That new job looks all shiny and awesome. “You can make X,” the Manager says, but WILL you make that?

When asked, “Why do you want to leave your current job?” This is an incredibly tough question because you know what they are thinking. Well, when will he leave us if he leaves the other guys? But, on the other hand, if you answer for the money, is money the only thing keeping you there? A bad job is not worth any amount of money.

Perceived PRO: It’s a Better Company to Sell For.

Perceived CON: You Could Get Better At Your Current Role.

Is the old job terrible, or do you need to improve? Tom was never in the top percentile at his SDR position and sometimes felt his managers didn’t give him the best leads.

He wanted to know more when a new job was dangled his way. His best friend (who got him the old job) cautioned him:

“You need to get better at all the things that make up this job. THEN if you want another job you can go knowing you gave it your all. Plus, you won’t leave with a good recommendation; you have never hit your quota.”

The big takeaway: The grass always looks greener, and perhaps it is green, but leaving before you have the numbers might leave you at a disadvantage.

Perceived PRO: It’s The Job I Want Now.

Perceived CON: It Doesn’t Lead to My Desired Job in 5-years.

Which job will let you grow to your highest potential?

Where do you want to be in 4 years?

An SDR’s life is not easy; it’s daily grunt work! Lots of emails. You’re texting, cold calling, sending white papers, and doing social media work. But, in the long run, it has a logical payout- the coveted Account Executive position. So here is the question: is your SDR Position getting you there? Are you heading toward becoming an AE?

These are things to consider before changing jobs. What is your current agreement with your Sales Manager about getting you to the AE position? Do you believe her? Letting your current Manager know how hungry you are for the AE position might change the dynamics of your current position. Your Manager could fast-track you; quitting would cut off that path.

Perceived PRO: It’s a Hungry Startup With Lots of Potential.

Perceived CON: Last Hired Is Often First Fired.

When Martin came into his new AE position, everything looked great. Then, the last quarter’s numbers came in lower than expected, and the funding dried up. His position was the first to go. “I wish I had spent more time looking at the bottom line details. They were struggling, but all I saw was the money.”

Startups can be heavy with egos struggling to survive. Is it the environment? Is the sales floor an uncomfortable, competitive, and toxic environment? How do you explain this? Try outlining the environment you work best in. Do you thrive in silence, or does the loudness drive you to new heights? I’ve worked with many salespeople who actually struggled in quiet environments. Personally, I love them. Making a move to find a place where you can work better is a narrative that works.

Perceived PRO: A New Product, A New Sales Process

Perceived CON: You Are Now The New

How long will it take to get you up to superstar speed? First, spend time on the floor or mirroring a top performer. Ask them, “How long until I can do what you do?” Then double it, just to give yourself breathing room. Is that a comfortable amount of time? Pros: You get to learn a new product, a new system. It’s a basket full of new. I thrive on this; I’m a quick learner. I’ve worked with several reps who take a long time to ramp up, which can cause stress in a new work environment. Some people need change; new ideas energize them. When I study the number of reps who give up, I see a trend of not seeing the act achieved in the daily grind. Did you give up too early to even make a good decision?

Perceived PRO: Feels Good To Be Wanted.

Perceived CON: Ignore Your Ego. Why Do They Want You?

What is the real reason you want to leave? Is it an incredible ego rush to hear from a recruiter saying all the right things? “We have heard great things about you!” Being wanted by another company feels good. However, this new car smell wears off quickly if the numbers aren’t delivered. Then what happens? Are you prepared for the worst as well as the best? Asking the company why they think you would be a good fit for them. This can be very illuminating. Explain how you work best, and ask to examine the environment you will sell in before determining if it will work for you.

We are blessed and cursed in the sales profession to have such a rich and vibrant market to earn our living. However, with success comes the inevitable call or text from the recruiter. Whether we decide to take the job offer or to stay depends on many factors, and a critical eye to decide which is which.

If you have decided it’s time to find a new sales job, create a profile on Rainmakers and start browsing companies that are now actively hiring!

essential sales books for beginners

Sales books provide a glimpse into the mind of another individual without the need for them to actively share their time. Their knowledge and experiences have already been eternally transcribed within the pages of their books for anyone to read at their leisure. Unfortunately, sales happens to be one of those things that you’d expect to be fairly straightforward but aren’t in practice. For that reason, we’ve listed five essential sales books for beginners. Study these to build a robust and powerful foundation for your sales career!

1. How to Win Friends & Influence People, by Dale Carnegie

This book is an absolute classic and a must-read for any sales professional. It’s probably the book you’ll hear referred to the most throughout your career. It’s simply that powerful. Though written over 80 years ago, much of the advice in his book still holds to this day. The book deals mainly with how to best communicate with other people by avoiding potential conflicts and proactively working to make a good impression. As such, this can be an excellent read for all kinds of folks, not just those working in sales. Anyone who deals with people for a living would benefit greatly from reading the teachings of Dale Carnegie.

Check it outHow To Win Friends And Influence People

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2. Secrets of Closing the Sale, by Zig Zigler

Zig Zigler is a renowned author, sales coach, and motivational speaker. If you do a quick YouTube search for his name, you’ll find a long list of videos from his speeches, interviews, or other segments where he’s given his knowledge and advice to others. If you have the time to look through a few of them, it may be worth your time, but his book will undoubtedly provide you with strategies and guidelines to make you as persuasive as possible. It’s also a relatively quick read, so it would be worth adding to the reading list for those looking for a new book to get through.

Check it outSecrets of Closing the Sale

3. To Sell Is Human: The Surprising Truth About Moving Others, by Daniel H. Pink

Here we have another book that seems to get a lot of love and attention from many professionals in the world of sales. I’ve heard this book gets mentioned in conversations on several occasions from various networking events. Having only been published in 2012, it’s a very recent book as well.

Within its pages, Pink talks about the correlation between persuasion and selling. He also outlines that regardless of your profession, a challenge that comes up quite frequently in life is the ability to effectively persuade someone else of an idea. Whether it’s getting children to do their homework or convincing a significant other to eat at a restaurant of your choosing, there is always an element of persuasion or selling necessary. Thus, Pink can derive the name of his book from this basic principle.

Check it outTo Sell is Human

best books for salespeople

4. Predictably Irrational, by Dan Ariely

Now this book doesn’t mainly focus on the art of sales or how to improve your persuasion directly. Still, it provides some fascinating insights into common mistakes most people have in their thinking. For example, Dan Ariely proves in a series of experiments that although, in theory, you would think that everyone would make the most rational decision in every situation, that’s not the case. Even more so, people seem to make the same irrational decisions predictably.

If you’re interested in learning about these common falsehoods in people’s thinking, possibly even your own, this is another excellent book to add to your reading list. As a quick bonus, if you want more from Dan Ariely and his research, he recently published another book called Payoff, which dives into the hidden logic of things that shapes our motivation.

Check it outPredictably Irrational

5. SPIN Selling, by Neil Rackham

This book will likely provide you with some of the most tactical advice you can use immediately in your sales career. The book is titled after the selling methodology of the same name it evangelizes. SPIN is an acronym for Situation, Problem, Implication, and Need-Payoff. Each part of the acronym relates to the different questions you should be asking to help build interest in your product or service within the prospect and effectively guide them through the sales process.

Many of you are likely already familiar with the BANT criteria for validating a sale. This is essentially taking that concept and flipping it on its head, where you can now use the same criteria to validate the sale to the prospect rather than to yourselves internally.

Check it outSPIN Selling

tips for being a better salesperson

6. New Sales Simplified: The Essential Handbook for Prospecting and New Business Development, by Mike Weinberg

Mike Weinberg runs his own sales consultancy, and it is safe to say that he knows something about sales. He played a pivotal part in the successful growth of SlimFast in the early days, a story he talks about within his book. But, outside of his successful sales journey and the experiences that helped guide him to where he is today, he outlines an excellent framework that’s easy to follow and leverage.

He provides best practices to productively kick off your sales process with ideas and tactics that have served him and his many clients well over the last several years. He goes over everything in great detail, from approaching the prospecting process to getting mentally prepared to hit the phone with the right message. This is a must-read for newer sales professionals and a great refresher even for those who are more seasoned.

Check it out New Sales Simplified

7. Hacking Sales, by Max Altschuler

Max Altschuler was a crucial player in the explosive growth of Udemy. He explains the process he used to prioritize his prospects and key community members to get things going quickly during the infancy stages of the company. He’s since had a very successful career providing consulting work and founding an organization known as Sales Hacker. Like Mike Weinberg, Max took his advice and wrote this book for all salespeople to benefit from. He presents his ideas in a very understandable fashion. In addition, he offers more specific tactics around the sales technology tools available on the market and how to use them to your advantage effectively.

Check it outHacking Sales

Recap: 7 Essential Sales Books For Beginners

Of course, this is not to say that these are the only sales books worth reading. You can read tons of other books to improve your ability to sell, like Predictable Revenue, Think and Grow Rich, The New Strategic Selling, The Challenger Sale, Endless referrals, and so many more. In addition, some books can teach you to be a better sales coach or leader, like Coaching Salespeople into Sales Champions. Honestly, the list of books you can read in this realm can go on and on. This list should be a great starting point for your new sales reading journey. Finishing these seven books should give you a solid foundational understanding of thinking about and executing your selling ability.

Get approached by tech companies offering tech sales jobs at Rainmakers.

questions asked during sales interview

Popular Interview Questions

This article will fully summarize the four most common sales interview questions and give you the best possible answers!

Conduct Your Job Interview Like You Would The Sales Process

Whether you love or hate it, interviews are essential to the hiring process. That’s why you must be well prepared to handle any interview questions coming your way when you’re trying to get a job in tech sales.

Failure to do so will not bode well, as your potential employer might worry about how you will handle objections while on the job. How you take the questions thrown at you during the interview could make or break your chances of getting an offer, so make sure to answer them confidently.

Keep in mind that in a sense, the interview is very much like a sale, wherein you are the product and the company is the buyer.

Leverage this dynamic to your advantage and use the interview as a platform to showcase the various strategies and tactics you would use on the job. What better way to prove you’re the best candidate than to have the interviewer see you in action?

Below is a short list of 4 general questions asked during many tech sales interviews. Let’s take a moment to dig deeper into each one and identify the best ways to approach them.

best interviewing tips

1. Why do you want to be in sales? 

This question is an absolute classic and is almost guaranteed to come up during your interview. In asking this question, the interviewer is trying to understand your motivation. What about sales excites you and makes you want to get out of bed every morning?

Don’t stop with simple and vague statements like:

“I live and breathe sales” or “I’m just a natural-born salesperson”.

Provide examples that back up your claims. For example, what have you done that demonstrates your excellent sales abilities?

Why have these events influenced your decision to pursue a career in sales? What about your character and skills make you a good fit for a sales career instead of another field?

To ace this question, you need to leave the interviewer feeling there will be no need to worry about your motivation should you get hired.

They need to have that sense of confidence that even if they’re not always around to see you, you’ll have the ability and the self-motivation to stay focused and continue to perform.

tips for interviewing

2. What do you know about our company?

This question can be phrased in many ways, but ultimately, the interviewer is trying to see how well prepared you are. Therefore, use this question as a springboard to demonstrate your research prowess since it’s an extremely valuable skill for any tech sales professional.

If the company is public, you can read through their annual report or 10-K to find some golden nuggets of information, like their goals for the year or what they foresee as being some of their biggest challenges.

If instead, you’re interviewing for a private company or even a startup, there is still a wide range of resources at your disposal. Crunchbase is an excellent website for information on companies, especially early tech startups. Owler is another excellent resource you can use to find recent news about any company.

And of course, checking the company website and doing a quick Google search for the company name is a great way to get a high-level understanding of their business. At the very least, you want to understand who their customers are and how they differ from the other competitors in the space.

Try your best to piece things you find in your research together to show off your analytical skills and ability to see the bigger picture. For example, suppose you can prove you have a good understanding of the company’s environment and what its current situation means from a business perspective. In that case, there will be no doubt in the interviewer’s mind that you can do the same for your prospects and have meaningful business conversations.

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3. When was the last time you took a significant risk that didn’t pan out?

Another one that would be very similar to this would be the “What’s your greatest weakness?” question. Both of these questions require you to have a strong enough understanding of yourself to recognize your limitations. All of us are human, and none of us are perfect, but recognizing where your imperfections lie requires a strong sense of self-awareness.

Being able to point out where you could improve also demonstrates your ability to be coached which is something many hiring managers like to see in their candidates. On the other hand, someone who is completely stuck in their ways and unwilling to re-evaluate their approach can be tough to work with. Therefore, if you give the impression that you’re one of these candidates, the hiring manager may pass on you to save them from future frustrations.

This particular question differs from the ‘greatest weakness’ question because it goes one step further by gauging your risk tolerance and ability to take calculated risks. When listening to your experience, the interviewer tries to understand how you approach a risky situation, what you take into consideration, and how you ultimately factor everything into your final decision.

There is no one correct answer to this question, but there is one thing you always need to do with your response. Be clear and convincing.

Just like with question 1 on this list, there is no one correct answer or approach to this question, possibly even more so because it depends greatly on the company’s and interviewer’s tolerance for risk. Whether risk-loving or risk-averse, you want to provide an example that closely aligns with their preferences.

Your research can sometimes give you a good sense of the company’s risk tolerance. Additionally, if you’re good at reading people, you can often tell by the interviewer’s body language how aggressive of a personality they have. The more aggressive they seem, the more likely they’ll have a higher tolerance for risk. If all else fails and you can’t understand where they stand, err more on the higher risk side. After all, you are trying to work in sales. Sales managers would instead hire someone who can take action on a well-thought-out scenario than the other way around, especially if the candidate has already proven that they are very coachable.

To prove that you are indeed coachable, think back to an experience that didn’t go as you wanted and explain the lessons you learned from that experience. Bonus points if you can even talk about how you continue to use those lessons to this day. By doing this, you’re illustrating that you are someone who inherently focuses on self-improvement and embraces change for the better.

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4. Do you have any questions for me?

Though seemingly innocuous, this question can be pretty loaded. A candidate’s answers to this question reveal a lot about their character.

A lot of the time, you may have legitimate questions about the job that are left unanswered, and this is the right time to ask those questions. However, as a fair warning, it would be highly advisable not to make every question about the company’s benefits or what you stand to gain from the position. Instead, though they may be necessary, try to sprinkle in some additional questions around anything unclear about how you’d actually do your job. You can probably get many simple answers to your benefits questions by doing a little research on the company’s Glassdoor profile.

That way, you can ask other questions more relevant to the job at hand during the interview. For example, what tools will you be using? What are everyday struggles they see with new hires coming on board? What have others before you done to succeed? Try to think more along these lines, as this will convey to your interviewer that you are serious and excited about the work.

This is almost always the last question asked during the interview, so don’t squander the opportunity to make a great final impression. Instead, utilize the peak-end rule to your advantage and go out with a bang to ensure you have the highest chance of getting that job offer.

Lastly, remember that just as much as the company is trying to evaluate your fit into their business and available role, you should also be assessing the fit of the position to your personal preferences. Everyone is different, so if certain things about a job are essential for you, make sure to touch on those as well. The last thing you’d want to do is hastily join an organization just for the sake of getting a new job only to find out soon after that you made the wrong decision and, even worse, may have to go through the whole job search process again because you joined the lousy company.

PS – Check out this video below by Richard McMunn for another in-depth look at the most common sales interview questions and the best ways to answer them:

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ai future of sales

It’s no secret that we’re currently on the brink of an unprecedented AI revolution. Over the past few decades, technology has quickly taken over the way we live. Many of us today use our computers to make a living and it’s now simply the cultural norm to rely on technology as your primary source of entertainment among many other things.  

With the vast efficiencies and capabilities that technology brings, it’s easy to understand why technology has become so omnipresent in our lives. What would have taken our ancestors weeks to write on a manuscript can now be drafted in a matter of days on any word processor. In the past the speed at which this process could be completed was limited by the speed at which you could type but now we can draft as quickly as we speak thanks to modern voice to text technology, granted edits will be necessary. However, in the near future there will come a time when our computers can not only transcribe our words but also revise it to a final draft for us. In fact, it will actually be capable of accomplishing a great deal more than that.

The driving force that will deliver us these amazing new capabilities is called natural language understanding which is a subtopic in the broader field of artificial intelligence. We’re not there yet but it’s only a matter of time before a computer is built that will have the ability to code changes into itself. Soon thereafter we’ll be dealing with what is called artificial-superintelligence which is AI that achieves a level of intelligence greater than all of humankind. It would be too lengthy to discuss this idea in its entirety as well as its ramifications for society but if you’re curious to learn more about it, this is actually a really good article that does an amazing job of providing a comprehensive overview of the current state of AI and where its headed.

Instead this article will focus on the impact that AI will have on the professional world of sales. Like many other sectors, salespeople will see their jobs being impacted in some way or another by artificial intelligence with many of them possibly even losing their jobs to it. NPR put out an interesting interactive that provides predictions of how likely your job is to be taken over by a machine if you’re curious to check that out. AI will indeed have an impact on blue-collar jobs but interestingly enough data shows that in fact there are many more use cases that threaten the security of white-collar jobs than blue-collar ones. We’ll touch more on what this means for the modern sales professional a little later in this article.

For the most part though we can expect that in most instances AI will augment rather than replace the work that we perform. We’re seeing the the start of this already with a myriad of AI business solutions like Einstein from Salesforce. Einstein currently offers things like predictive lead scoring,  lead insights, as well as predictions and alerts for high priority opportunities with a strong likelihood to close. That’s not to say though that Salesforce is the only player or the best vendor in the space.

There are a tremendous number of other businesses as well that are trying to leverage the benefits that AI offers for commercial success. These include companies like, Spiro, Clearbit Connect, LeadCrunch and Crystal, each of which provide some very interesting value propositions. is a virtual assistant who schedules meetings on your behalf by proposing free times and automatically sending calendar invites for agreed appointments. Spiro is another type of virtual assistant but one that’s focused on helping sales professionals stay focused on top prospects by sending reminders and notifications based on previous activity within a deal cycle. Clearbit Connect is a gmail plugin that’s leveraging AI to streamline the arduous process of prospecting by taking care of the search for emails and LinkedIn profiles for you. LeadCrunch is another notable business assisting in the prospecting realm and one that helps identify new potential customers based on your existing customer profiles. The final business on our list, Crystal is a service that’s looking to coach sales professionals on how best to reach out to their prospects by considering their personality and communication styles.

Understandably to some of you these products may seem gimmicky and to others it may simply be more money than you’re willing to pay for the benefits. However the underlying message here is not that these are all businesses or services we need to be taking advantage of right now. Rather, what should excite us is the fact that we’re seeing seedlings of what will soon be a technological revolution that will bring tremendous convenience to the everyday sales professional that has never been available before.

For the average salesperson this would mean they no longer have to deal with manual data entry and will instead have a future CRM that can automatically track and log all of their activities for them. Companies like Sudo are making the early inroads towards making this ethereal vision a reality through a virtual assistant chatbot. Though a chatbot isn’t the minimal user interface CRM that you may be imagining it’s again important to recognize that these are the initial steps towards a more convenient future.

Thanks to Moore’s law what is a chatbot today can quickly evolve into an intelligent personal assistant that’s possibly even more advanced than the ones we carry around in our smartphones today. Additionally, this same CRM could possibly even prospect and conduct outreach on our behalf while leveraging the benefits of increased insights better than any human ever could.

And as time continues, mergers and acquisitions as well as more efficient development cycles will lead to the merging of the many capabilities we’ve discussed so far which should be even more exciting news to the modern sales executive.

A future with artificial intelligence will likely mean a future where professional data is so abundant, connected and available that records can be updated in real time eliminating the whole notion of “dirty data” or outdated information.  Reports and summaries could be built in a matter of minutes upon verbal request to a computer and the costly process of finding and building target lists can be as easy as asking, “Computer, what is my addressable market?”.

What this means for the modern sales professional is that you’re life is going to get a lot easier over the next few decades but only if you have a sales job that isn’t likely to be automated by a machine. This technological revolution won’t take place tomorrow or next week but it’s important to understand that it is indeed a serious and imminent trend and one that needs to be taken into consideration when planning for your career. The best way to understand whether or not your job has a high likelihood of being automated is to look at your job description. The more your work is repetitive in nature and requires little to no cognitive judgement to complete the more likely your job is to be replaced by a machine because the financial and productivity incentives for businesses will be too strong to ignore. These would likely be roles in an administrative, business development or otherwise entry level function in a sales organization.

The next most likely group to feel pressure on their job security are those that are charged with maintaining a sales process or system. Reason being, at the moment these duties do require some level of human oversight but there will be a time when AI evolves from artificial narrow intelligence to artificial general intelligence and because a machine has no need for food, sleep, insurance or a raise, it’s inevitable for businesses to start replacing some of their workforce with these machines. This would probably apply to many folks working in a sales operation capacity.

The jobs least likely to be impacted and taken over the pending AI revolution are those that inherently requires some human element of thought or trust. Because humans are social creatures, no matter how efficient machines can become and how closely they can resemble our intelligence, there is a level of human trust that can’t be built up with a machine. As such there will always be some need for “human” reassurance in business. These roles will likely revolve around things like sales strategy, contract negotiations, training or coaching and the like.

If you want to learn more on how to slowly develop a career path towards these kinds of roles, check out the Rainmaker platform for sales professionals. There you can check out new opportunities are there for your in the next step of your sales career and also see how you stack up against your peers. It’s a great resource to get a better understanding of your professional competency and to make sure you’re not leaving any untapped opportunities on the table.

-Dean Park

Dean Park is a seasoned tech sales professional that’s been involved with a wide range of organizations from startups to enterprise businesses. Dean is also a sales mentor at GrowthX Academy in San Francisco.

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