Being the Founding SC with Alex Margolis
Alex Margolis discusses his experience as a founding SE at an early-stage company, explaining how the role differed from his expectations of strategic leadership. He emphasizes the importance of setting boundaries, building cross-functional relationships, and ensuring cultural fit when considering founding SE positions.
Summary
Alex Margolis, currently a Senior Sales Engineer at Freshpaint, joined the PreSales Podcast to discuss his experience as a founding SE—the first sales engineer at an organization. He deliberately targeted founding SE roles to accelerate his career progression, having spent six years at a 300-person company where traditional advancement paths were limited. After interim leadership experience, he sought a role where he could establish team structure and processes from the ground up.
When Alex joined his founding SE role, he discovered that despite initial promises of strategic responsibility, the position evolved into primarily demo execution. The company had eight AEs, numerous BDRs, and extremely high meeting volume. Though the VP of Sales initially covered many demos, Alex ended up supporting a 6-to-1 AE ratio while simultaneously building processes and infrastructure. He found himself doing approximately 40 demos monthly, with roughly half coming from teams outside his intended scope, leaving minimal time for strategic initiatives like cross-functional collaboration with product, PMM, and post-sales teams.
A critical lesson emerged when Alex analyzed his workload after three months: he discovered that half his demo work came from teams he wasn't supposed to support. He recognized he should have drawn firmer boundaries earlier, particularly by limiting his scope to mid-market and enterprise accounts while declining to support the high-volume small business segment. This taught him that pre-sales professionals must actively prioritize between supporting high-volume deals, strategic enterprise deals, and go-to-market initiatives—and that without clear boundaries, organizations will naturally expand demands.
During his interview process, Alex had been told the role was individual contributor focused, not a formal leadership position. However, he positioned it differently internally, framing the work as building scalable processes. This misalignment between his expectations and the company's actual needs—which required immediate execution rather than strategic infrastructure building—ultimately led to his departure. He recommends that future founding SEs should deeply investigate actual demo volume, scrutinize growth projections, and honestly assess whether the company needs a strategic builder or an execution-focused grinder.
Alex emphasized that the best founding SEs should be comfortable working outside their comfort zone, building relationships across product, engineering, marketing, and post-sales teams. He highlighted the unique isolation of being the only SE and stressed the importance of organizational fit, noting that cultural alignment matters significantly given how much time people spend at work. His current role at Freshpaint—where he was referred through his wife's connection and was impressed by the company's published "no assholes policy"—exemplifies this prioritization of workplace culture alongside career opportunity.
About this episode
<p dir="ltr">Alex Margolis joins the show with cohosts Jack Cochran and Mathew James to share his experience as a founding sales engineer, pulling back the curtain on what it's really like to be the first SE at a startup. Alex discusses his deliberate decision to target founding SE roles as a way to fast-forward his career after six years at a company with limited growth opportunities, expecting to build processes and lead strategically from day one. Instead, he found himself supporting eight AEs and an equal number of BDRs, running five demos a day in a high-velocity sales environment that left little time for the strategic work he'd been promised.</p> <p dir="ltr"><span style="font-size: 18pt;"><strong>Follow Us</strong></span></p> <ul> <li dir="ltr"> <p dir="ltr">Connect with Jack Cochran: <a href="https://www.linkedin.com/in/jackcochran/">https://www.linkedin.com/in/jackcochran/</a> </p> </li> <li dir="ltr"> <p dir="ltr">Connect with Matthew James: <a href="https://www.linkedin.com/in/matthewyoungjames/">https://www.linkedin.com/in/matthewyoungjames/</a> </p> </li> <li dir="ltr"> <p dir="ltr">Connect with Alex Margolis: <a href="https://www.linkedin.com/in/alexnmargolis/">https://www.linkedin.com/in/alexnmargolis/</a> </p> </li> </ul> <h2 dir="ltr">Links and Resources Mentioned</h2> <ul> <li dir="ltr"> <p dir="ltr">Join Presales Collective Slack: <a href="https://www.presalescollective.com/slack">https://www.presalescollective.com/slack</a> </p> </li> <li dir="ltr"> <p dir="ltr">Presales Collective Podcast: <a href="https://www.presalescollective.com/podcast">https://www.presalescollective.com/podcast</a> </p> </li> </ul> <h2 dir="ltr">Key Topics Covered</h2> <ol> <li dir="ltr"> <p dir="ltr">Motivations for seeking founding SE roles and fast-forwarding your career</p> </li> <li dir="ltr"> <p dir="ltr">The sales assistant trap: expectations vs. reality of strategic involvement</p> </li> <li dir="ltr"> <p dir="ltr">Supporting eight AEs plus BDRs as the only SE in a high-velocity environment</p> </li> <li dir="ltr"> <p dir="ltr">Setting boundaries and tracking workload to prioritize effectively</p> </li> <li dir="ltr"> <p dir="ltr">Cross-functional relationship building as the company "facsimile"</p> </li> <li dir="ltr"> <p dir="ltr">Interview questions to ask when evaluating founding SE opportunities</p> </li> <li dir="ltr"> <p dir="ltr">Who the right fit is for high-volume founding SE roles</p> </li> <li dir="ltr"> <p dir="ltr">Finding company culture fit and working with good people</p> </li> </ol>
Key Insights
- Alex discovered that half of his 40 monthly demos came from teams outside his intended scope, demonstrating how founding SEs can be pulled into unintended work without explicit boundary-setting early in the role.
- The VP of Sales at Alex's company actively ran demos alongside him, an unusual arrangement that revealed the company prioritized immediate execution over building a dedicated pre-sales function, which conflicted with Alex's strategic intentions.
- Alex's interview process failed to uncover critical misalignments because he took growth projections and demo volume estimates at face value rather than requesting detailed data to verify whether the company's needs matched his career goals.
- Alex argues that founding SE roles can be appropriate career transitions for mid-level SEs or professionals moving from adjacent functions (like post-sales) who need high-velocity reps, but not for those seeking immediate strategic leadership.
- Sales engineers function as organizational liaisons who must maintain relationships with product, engineering, PMM, and post-sales teams to be effective, yet founding SEs often face competing demands that prevent this cross-functional work despite its importance.
Topics
Transcript
So Matthew, I think there's something that doesn't happen much anymore. I'm actually very happy it doesn't. I don't remember back in the early days, people would have blogs and like when social media was first coming out, whenever someone would post something, what's the first thing you would see in the comments? Is it first? That's the one. Yeah, that first comment. As soon as you post, people wouldn't even read what you wrote. Someone had to be first, just saying they were first. You have four people trying to say first at the same time. I was thinking about that today because that's a terrible use of being first. But what about being the first SE at an…
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