EP 13 - From Writer to Founding AE: How a Fractional Services Seller Tripled Inbound Close Rates

What happens when a writing & PR major becomes an early sales hire at a fractional back-office firm - and 3x’s inbound close rates in under two years?In this episode of The Founding AE Podcast, Justin Dorfman sits down with Will Oberndorfer, Business Development Representative at Milestone, to unpack what it’s really like selling fractional accounting, CFO, HR, and payroll services versus SaaS - and why understanding the customer deeply can beat a “logo-heavy” sales resume any day.You’ll hear how Stompbox (https://stompbox.io/) helped Will build a real sales foundation, why referrals and inbound are Milestone’s growth engine, and how he thinks about outbound, events, and qualifying the right clients in a trust-heavy services business.In this episode, we cover:🧩 Selling services vs. SaaSHow fractional back-office work (bookkeeping → controllership → CFO + HR/payroll) changes the sales motion compared to traditional software demos.🏗️ How Stompbox built Milestone’s sales foundationGoing from 15% to 35–37% inbound close rates by tightening discovery, running better meetings, and systematizing follow-up.👤 Why Will was chosen over a “proven” sellerThe upside of promoting someone who knows the product, team, and customers - and then teaching them sales the right way.🤝 Referrals as a pipeline engineHow Milestone works with lawyers, VCs, business coaches, and local networks to generate high-intent inbound and warm referrals.☕ Events that actually move pipelineWhy small, intimate coffees, chambers, and local CEO groups outperform the big, noisy conferences for services businesses.🧪 Outbound for trust-based servicesWhy classic “cold outbound at scale” underperforms for accounting & HR - and how Will reframes outbound as intentional networking.✅ Qualifying clients as hard as clients qualify youHow Will screens for fit so his internal team actually enjoys working with the customers he brings in.💙 Tthe entrepreneurial mindsetHow running a nonprofit since age 14 shaped Will’s respect for founders and influences how he shows up in sales conversations.Timestamps00:00 – Intro: Why Justin wanted Will on the show01:05 – From Purdue writing/PR major to Milestone03:40 – What Milestone actually does (fractional accounting, CFO, HR & payroll)05:50 – Partnering with Stompbox + becoming sales hire #308:00 – Tripling inbound close rate: what actually changed10:30 – Inbound + referrals vs classic outbound13:20 – How Milestone structures its referral engine & incentives16:00 – Events that work: small, local, and intentional over big conferences19:00 – Selling services without a “product demo”22:00 – Qualifying for people fit in a services business25:30 – Creating urgency in accounting without fake pressure31:50 – How to connect with Will & support the nonprofitConnect with Will👉 LinkedIn: Will Oberndorfer: https://www.linkedin.com/in/william-oberndorfer-389b6616a/👉 Milestone: https://milestone.inc/If you’re a founding AE, founder-led seller, or early sales hire trying to figure out services, referrals, and relationship-driven selling, this episode will hit home.🔔 Subscribe to The Founding AE Podcast for more real, tactical conversations with the people building sales from zero.

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