This report shares insights from 41 Founding Account Executives on hiring, compensating, and setting up the first sales hire for success in B2B startups.
Dan Oakes is the founder of Startup Sales Consulting. He was previously the first employee and founding account executive at a venture-backed fintech, and now he helps B2B founders scale beyond founder-led sales. He holds a BS in mechanical engineering from the University of Michigan and an MBA from Stanford's Graduate School of Business.
I surveyed 41 Founding Account Executives. Here's what they had to say:
How to find your first sales hires and set them up for success
For B2B startups, the first sales hire (or Founding Account Executive) is the cornerstone of scaling the business beyond founder-led sales.
A great first sales hire will do more than just execute the strategy. They’ll steer the company into the right markets, provide critical feedback to the product team, and scale the GTM motion into an effective and capital-efficient process.
Many founders don’t get this hire right the first time, so I surveyed 41 Founding Account Executives (AEs) to share their perspectives on how to be successful.
Here’s the link to the ten-question open-ended survey and the link to request access to the raw responses. I’ve listed the questions below, along with key insights.
Why did you want to take the role as a first sales hire?
Understanding the motivation of folks who want this role is helpful for recruiting purposes.
Though every situation is unique, zero respondents answered this question, indicating they wanted to take this role for more cash.
Higher cash comp is a bigger driver for AEs to take on new roles at growth and mature-stage companies. It’s less of a driver for the AEs who want to take a Founding AE role.
Founding AEs want to be challenged, build something from the ground up, and learn from a great founding team.
How did you first connect with your employer to get the role as the first sales hire?
Lean on your network!
Of surveyed founding AEs, 44% landed their role through someone on the team or a mutual connection.
What would you recommend to founders as the ideal compensation structure for a first sales hire?
Getting compensation structure right is critical in ensuring your first sales hire is motivated to drive results.
Startups won't have a predictable or repeatable sales motion at this stage, so the comp structure shouldn't reflect this like it should for an AE comp structure at a growth stage or mature company.
What are the minimum experiences needed before becoming a successful Founding AE?
When recruiting AEs at mature companies, sales leaders typically look for a track record of success beating quota in previous selling roles.
This isn't a bad screen to de-risk applicants, but this shouldn’t be the only screen since the role of the founding AE is dissimilar to a sales role at a mature company.
Startups don't have a sales playbook or oceans of data on what has worked and what hasn't. The first sales hire needs to "figure out" the playbook AND execute.
Here are some snippets of responses:
“...Founding AE's are the hungry grinder types that on paper might not be as 'qualified' or 'experienced'. The 'experienced' won't take the risks associated with the first chair, and the hungry are looking for an opportunity to make a name for themselves…”
“...I wouldn't say anything is ABSOLUTELY necessary. Prior to my first time as a founding AE, I had been an SDR for 9 months and a closer for 6. Many would have considered me unqualified to be a founding AE but I ended up having a lot of success as it just fit my working style and personality very well….”
“...Understanding sales is good, but understanding the market is more impactful...”
“...A craving to learn and excellent communication, the rest of it falls into place as you go. Your first sales hire needs to be malleable and have some kind of connection or passion for the industry you serve or the business's model…”
What's something your founders did that set you up for success as a first sales hire?
"...My founders did a fantastic job by bringing me to the discussion table and genuinely listening to my customer feedback. When I shared insights from the field, they were quick to pivot and add the functionality we needed. They also gave me the room to fail, which was crucial. This support allowed me to experiment, learn from mistakes, and ultimately find the right approach for our sales strategy. Their openness and flexibility made all the difference..."
"...In the interview process, they opened up the CRM and the financials, and just let me ask questions to learn what was truly going on with the pipeline currently. I had zero surprises in my first week because I had made no assumptions, I already knew what the CRM looked like and what it needed to get to...."
"...They brought me to a conference in the first several weeks. This allowed me to practice my pitch hundreds of times and have a lot of customer conversations - also observe the founders repeatedly talk about the product and vision..."
What specific advice would you give to founders regarding ensuring their first sales hires are set up for success?
"...Ideally you have a predictable process for generating and closing deals and the sales hire is just to scale that. If you don't have this process in place, I suggest getting a mentor and figuring it out for yourself first...
"...Make sure [the founder] has been able to sell into the target market they're asking the first sales hire to sell into. This is AFTER they've exhausted their sweetheart deals and have managed a few full sales cycles with non-network customers."
"Set the AE up with some quick wins, referrals, let them take over ops founders have in place…"
What specific advice would you give to founders regarding recruiting and interviewing their first sales hires?
“...It’s more important for the AE to have a proven hard work ethic than seeing that they have sold a ‘blue chip’ product…"
“...Find the grittiest hustlers you can and then pay them well so you keep them..”
“...Ask them questions about legitimately what their gameplan would be in the first 30, 60, 90 days…”
“...Don't sugarcoat reality. The best candidates, the ones who are ready to get in the trenches, don't need a polished version of the truth…”
When should a founder hire their first sales hire? How early is too early?
“...I admire founders who grind and sell on their own to start. They need to prove out the value to a first sales hire and that they have a product that the market needs/wants. I think sometime after 20-30 sales...”
“...The best case situation is when there are key wins from an early founder sales motion and an increase in inbound queries…”
“...Founders need to have sourced and closed 10+ repeatable strangers from cold outbound. When you just close people in your network, it can fill you with false confidence/PMF...”
“...We were brought on before the product was fully ready, and our eagerness to close deals led to setting unrealistic expectations. The product couldn’t keep up, which caused issues with early clients. It’s crucial to have a bit of stability and proven use cases before bringing on a sales team to scale things up effectively...”
*Of the answers that referenced a specific customer count, every recommendation was 𝗯𝗲𝘁𝘄𝗲𝗲𝗻 𝟱-𝟯𝟬 (depending on ACV). “Customer count” is a broad definition; some responses specified “live” customers, or customers who have been using the product for a certain amount of time (i.e., six months)
**Of the answers that referenced a specific ARR level, every recommendation was between $𝟮𝟬𝟬𝗸 𝗮𝗻𝗱 $𝟱𝟬𝟬𝗸
Final thoughts
When done right, the first sales hire will turn the revenue traction you've built into a well-oiled GTM machine.
My three biggest takeaways from the survey responses are:
1) You need to have traction first.
2) Find the right candidate for this role - not the future role you envision once you already have hundreds of paying customers.
3) Ensure you set them up for success.
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