I surveyed 41 Founding Account Executives. Here's what they had to say...

Guest Contributor: Dan Oakes, Founder of Startup Sales Consulting

Dan Oakes is the founder of Startup Sales Consulting. He was previously the first employee and Founding Account Executive at Arc and later Head of Sales at Trunk Tools. Now he helps B2B founders scale beyond founder-led sales. He holds an MBA from Stanford's Graduate School of Business.

A great first sales hire will do more than just execute. They'll steer the company into the right markets, provide critical feedback to the product team, and scale the traction a founder has made into an effective and capital-efficient GTM motion. Many founders don't get this hire right the first time.

I wanted to understand what separates successful founding sales hires from unsuccessful ones. I surveyed 41 Founding AEs about their experiences, motivations, and advice for founders (complete survey results).  Here's what I discovered:

Insight #1: Why Top Performers Choose to Be First Sales Hires

Not a single respondent cited “higher compensation” as their primary motivation for taking on the founding AE role. Instead, they were more interested in learning how to build a business, many so that they could then become future founders.  The insight is key because it helps inform how a founder should think about traits to screen for and the types of interview questions to ask that help identify individuals that truly exhibit these traits.  

Insight #2: Effective Recruiting and Interviewing

Piggybacking off of Insight #1, the survey challenged conventional sales-hiring wisdom - sales leaders typically look for a track record of success beating quota in previous selling roles.  Instead, hiring should focus on candidates with:

• Focus on work ethic and resourcefulness over past quota attainment

• Genuine passion for the industry or problem space

• Adaptability and comfort working with constantly evolving products

• Self-motivation and ability to operate with minimal structure

• Resourcefulness in creating their own sales enablement materials

• Detailed questions about their 30-60-90 day plan

"Founding AEs 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….”

“...Ask them questions about legitimately what their gameplan would be in the first 30 60 90 days…”

One final thought here - as one respondent advised founders: "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."

Insight #3: How Founding AEs Find Their Opportunities

The survey revealed clear patterns in how these crucial hires connect with early-stage companies:

• 44% landed their role through team connections or mutual introductions

• The remaining paths included direct outreach, recruiter connections, and founder networking

• Several noted that their personal experience with the problem the startup was solving made them compelling candidates

Insight #4: Setting First Sales Hires Up for Success

Respondents offered clear guidance for founders:

• Establish a repeatable process for generating and closing deals before hiring

• Complete several full sales cycles with non-network customers

• Provide initial momentum with warm introductions and handed-off opportunities

• Maintain founder involvement in early sales cycles for rapid feedback loops

• Ensure product readiness for the target customer segment

"...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 opps founders have in place…"

Insight #5: Timing of First Sales Hire

The survey showed consensus on timing indicators - founders should validate their ability to sell to non-network contacts before bringing in dedicated sales professionals.  General guidelines:

• Customer Count: Every recommendation fell between 5-30 customers (varying by ACV)

• Revenue Milestone: All responses suggested between $200K-$500K ARR

• Validation: Multiple respondents emphasized having "10+ repeatable strangers from cold outbound" before hiring

Final Thoughts

My three biggest takeaways from the survey responses are:

1. Validate traction first: Founders must prove repeatable sales before hiring

2. Find the right candidate for this unique role: Look beyond traditional sales credentials

3. Set them up for success: Provide the resources, context, and support needed to thrive in ambiguous conditions

Want to see the complete results from Dan's survey of 41 Founding AEs? Click here for the raw data and expanded insights.