Hiring Scenario: What to Know While Deciding to Join A Sales Team for a Tech Startup

Getting hired as the first salesperson at a tech startup can be daunting. There is a lot to gain if you join the right company at the right stage. But, if you join a team who misunderstands early-stage sales operations and KPIs, or one with poor culture, you can be taking a step backward. It’s all preventable if you look in the right places and ask the right questions. So that’s what we’re going to show you how to do today.

So how do you make sure you’re finding the right fit for you?

I sat down with Michael Cardamone to record a scenario where I aimed to find out what he would recommend a first-sales-role candidate should do before taking a position at an early-stage tech startup.

Why Michael? He is ideal for this interview because he has a lengthy and successful career in tech from joining the revenue team at Box in 2008 as employee #25, to now being the CEO of Acceleprise, a B2B SaaS focused accelerator and fund founded in 2012.

Listen to the full interview:

Michael, how do you suggest salespeople search for and choose the ‘right’ early-stage startup?

Before answering that, you need to ask yourself what your goals are. How do you want this opportunity to play into your overall career? Are you trying to optimize for any upside potential? Are you trying to line yourself up for the next step in your career? Knowing the answer to this is crucial in finding the right startup that aligns with your personal and professional goals.

Going in as the first sales hire is high risk, and it can be easy to get drawn into a role because of the company culture or because of the new responsibilities or title you will be getting. Those things are important but not as important as your ability to execute the functions of a job with excellence. Your performance within the position, and the experience that comes from it, is what will shape the future of your career.

To start determining if an early-stage startup is the right fit, you should look at who the investors are and how well the CEO can talk about their market. Look at how their business is evolving and why they know they are going to win. This can be hard to tell in a Seed stage, so if you are optimizing for upside but also care about having a brand name company on your resume, Series A would be the right time to jump into a startup. At this point, you can more easily see the momentum and have more data points to make an informed decision about coming on board.

What are some of the tactics and strategies you suggest for early stage job-seekers, starting with who I should speak with internally, and why?

As a candidate to become one of the first salespeople, you should be able to speak with whoever has been selling to date, which likely will be Founder(s) or CEO. It’s important to understand what has been working and what isn’t and how they think about the sales role and what they want to get out of it. You should also speak with any customer success employees to really understand the pulse of the customers and get a feel for what the customer perspective is. If you’re able to, you could even reach out to current customers to get further insight into their relationship with the startup.

What about vetting my own potential employers?

It’s important to look into the background of who you’re going to be reporting to. Were they successful in building teams in the past? Do they have experience in this industry? Finding out about past and current roles, and how they align into the current product, is useful for making sure it will be a good match.

Learn about the CEO’s background, if it wasn’t in sales, what was it? Ask yourself if they will make a good leader. Do they speak well about the product and inspire you? Do they advocate for good company culture? Try to research some of these questions and use the answers to aid how you move forward.

As a new salesperson, how do I make sure I’m not stepping into a bad situation for prospecting, demand gen, and hitting quota?

In some situations, you may find a company that gets an influx of leads from raising a C Round or getting positive PR. Their natural reaction will be to hire a salesperson who comes from a large “brand name” company who used to get leads handed to them on a silver platter – an experience that doesn’t fit the style of selling at an early stage startup. Once the new salesperson blows through all the leads generated from the raising the C Round or PR, they will be asked to generate leads at the top of the funnel and bring them to a close, something they likely don’t have experience doing. That’s why it’s important to set the expectations early on and have discussions on the short and long term duties required for the role. Understand if the pipeline is growing consistently, what the inbound channels are, how repeatable are they, how do you determine who is qualified, etc.

If sales have been founder-lead and you’re going to be the first sales hire, be sure to understand factors like how much time they spent selling, how many customers they sold and at what price point, what will be expected of you and how your success will be measured.

What should my next steps be?

Start doing your research. There are a lot of paths you can go down for seeking the perfect startup to work for, but one last way is to reach out to some of the top VC firms in your area and ask them for help getting in contact with some of their portfolio companies. They want to be helpful to their businesses, so you should try leveraging them to get introductions to the right people. There are also local resources like BuiltIn that host career-building events which may be helpful in your search.

If you’re looking for more information on joining a tech startup as a sales position, or even if you come on at a higher level like a CRO or VP,  be sure to seek out the Revenue Collective and Sam Jacobs, they have some great resources for helping their members advance their career.

If you are seeking this type of hire OR looking for the best early-stage tech organization to join as a salesperson, head to the home page of Rainmakers.co to get started.

Additional Links and Information:

To get involved in Acceleprise as a pre-seed SaaS company, you can apply for upcoming cohorts in SF, NYC, and Toronto.

Connect with Michael Cardamone on Linkedin

Follow Michael Cardamone on Twitter 

Follow Acceleprise on Twitter