EP 5 - From Teacher & Golf Pro to Founding AE: Curiosity, Cold Calls, and Building the Sales Engine

What does it really take to be a Founding AE? In this episode, Justin Dorfman sits down with Ben Sklar (Founding AE, Pivotly) to unpack his winding path from school teacher & golf pro to tech sales, why “founding” means building for scale, and the gritty motions - power dialers, events, LinkedIn, and relentless curiosity - that move early-stage deals forward.

Ben shares the mental game behind the role, the tools and assets he set up from scratch, and practical advice for anyone considering the leap from a well-resourced sales org into a tiny, fast-moving startup.

What you’ll learn

-How a non-traditional background can be a superpower in early-stage sales

-The real differences between AE at a mid/late-stage company vs. Founding AE

-Why curiosity and patience are table stakes - and how to manage the mental swings

-The tech stack that actually matters on Day 1 (and what can wait)

-Cold-calling at scale (power dialers), turning events into pipeline, and “semi-warm” outreach

-How to design discovery for complex, technical products

-Why “founding” means building repeatable processes for the next AE

Chapters:

00:00 Intro

00:38 Ben’s unconventional path: teacher → golf pro → tech

03:04 Pandemic pivot & first BDR role

06:36 Moving into healthcare & self-education (HealthTechNerds)

06:39 Landing at Pivotly: solving integrations & the “golden layer of truth”

10:59 Why choose a Founding AE role (timing, personality, risk)

12:18 The “smack in the face” differences at an early-stage startup

14:02 Learning the lingo & owning the entire sales workflow

16:18 “Founding” = build processes that scale for the next hires

17:21 Tools: Apollo, HubSpot, Microsoft 365/Azure, power dialer

19:44 Assets that matter: cold call & discovery scripts, demo flow

22:28 Cold calls still work (especially post-event lists)

23:24 Events, in-person motion, and fast follow-ups (yes, via text)

26:27 Soft skills & the mental game (golf mindset)

28:33 Advice Ben would give himself on Day 1

30:41 Where to find Ben & learn more about Pivotly

Tools & communities mentioned

Apollo (prospecting)

Power dialers (for high-volume connect rates)

HubSpot CRM Microsoft 365 / Azure

HealthTechNerds (healthtech community)

Connect with Ben on LinkedIn: “Ben Sklar — Founding AE at Pivotly”: https://www.linkedin.com/in/ben-sklar-80510aa3/

Pivotly: pivotly.com

If you enjoyed this, hit Like, Subscribe, and drop a comment with your biggest takeaway - or the one motion you’re going to test this week.

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