EP 15 - Selling SaaS to Contractors Channels, Objections, and the Local GTM Advantage

EP 15 - Selling SaaS to Contractors Channels, Objections, and the Local GTM Advantage

We’re closing out 2025 with a real Founding AE conversation.In this episode of the Founding AE Podcast, Justin Dorfman sits down with Matthew Smith, a multi-time Founding AE and current early hire at Permit Rockstar—an AI-driven platform helping construction companies with permitting, inspections (including virtual), and plan review.Matthew shares what it actually looks like to build go-to-market from zero when you don’t inherit a polished playbook—no CRM, no scripts, no templates… just a product, a couple lead lists, and the pressure to create pipeline fast.We cover:Why Matthew keeps choosing the Founding AE seat (and what makes it worth it)How he learned a brand-new vertical by “getting dirty” (calls, questions, reps, real-world context)What existed when he joined (spoiler: not much) and what he had to build from scratchThe must-have early-stage stack (HubSpot, Dialpad, Instantly, Slack… and why simplicity wins early)What channels are working in construction tech (trade shows, local associations, cold calls, email, LinkedIn, paid, referrals)The trade show playbook that led to 20 meetings booked at the boothWhy “start local” can be a superpower (and when it’s not worth the ROI)Common objections in construction - and why the “wrong persona” kills deals fastHow they’re thinking about ROI (and why rounding down builds trust)Matthew’s advice to first-time Founding AEs: team evaluation, ownership, self-sufficiency, and knowing when to clock outIf you’re a Founding AE (or hiring one), this episode is packed with practical, boots-on-the-ground lessons you can steal immediately.Connect with Matthew / Permit Rockstar:LinkedIn: https://www.linkedin.com/in/matthew-smith-sales/Website: permitrockstar.com (book a meeting/demo with Matthew)👍 Like, subscribe, and drop a comment: What’s the scrappiest thing you’ve done to generate pipeline at a startup?💪 Try FollowUp for FreeBack-to-back demos and follow-ups piling up? FollowUp instantly generates personalized Digital Sales Rooms from your sales calls—built for Founding AEs to move deals forward and enable champions to sell internally. Try it for free: https://www.gofollowup.ai/

EP 14 - $13M in Year One: How Founder-Led Sales + One Elite Founding AE Built a Rocketship

What does good founder-led sales actually look like in the AI era - and how do you successfully hand it off to a Founding AE without losing the magic?In this episode of The Founding AE Podcast, Justin Dorfman sits down with Tyler Pavlas, Founding AE at GrowthX, to unpack how GrowthX went from idea to ~$11M–$13M ARR in record time by combining:A ruthless focus on solving the #1 problem for CMOsA community- and content-first motion (before “selling”)A services-as-software model powered by AI workflowsAnd a very intentional founder → founding AE handoffTyler shares his journey from PwC strategy consulting to SDR, AE, and ultimately Founding AE at multiple startups - culminating in his role at GrowthX, where he’s closed millions in revenue and allowed CEO Marcel Santilli to spend just ~5% of his time on sales.You’ll hear how GrowthX helps companies show up in AI answers (AEO/GEO + SEO), why they’re drowning in inbound demand, and how Tyler thinks about qualification, ICP scoring, and picking the right customers when you can’t serve everyone.In this episode, you’ll learn:👷 Tyler’s path to Founding AE at GrowthXFrom PwC consulting to SDR outbounding to developersJoining early-stage startups like Rainforest, Segment, Air & CerosWhy his background in services + selling to marketers made him a perfect fit for GrowthX🚀 Inside the GrowthX rocketshipWhat GrowthX actually does for B2B companies investing in contentHow they help brands show up in ChatGPT / AI answers, not just GoogleWhy they call it “services as software” (AI workflows + human experts)🤝 The right way to hand off founder-led salesHow Marcel sold the early deals and built insane trust + demandWhat Tyler did in his first month (shadowing, learning the nuance, then scaling)How he closed ~$3M quickly without breaking what was already workingWhen he pulls the founder back into deals - and when he doesn’t✅ Qualification in a high-inbound worldWhy Tyler spends so much time on ICP definition and scoringThe 3-stage framework they use:Account DNA (domain authority, growth, funding, content volume)Engagement & excitement (urgency, trust, alignment, budget)Partnership fit (champions, approvals, expectations, “word babysitting”)How they say no (or “not yet”) without burning bridges🧰 Tools & AI workflows in Tyler’s sales processHow he uses AI (Claude, etc.) for: research, deal prep, and CS handoffWhy he rarely re-listens to full call recordings anymoreClay, SEMrush, Nooks, HeyReach, and how they fit into the motion🌐 The AI-Led Growth community & motionWhat members get inside AI-Led Growth (workshops, courses, community)How community + events create trust and long-term demandWhy “give value first, sell later” still wins - even in an AI-saturated worldWho this episode is for:Founders hiring (or thinking about hiring) their first AEFounding AEs figuring out how to step into a hot, inbound-heavy environmentCMOs & growth leaders trying to show up in AI + search resultsAnyone obsessed with the intersection of AI, content, and B2B revenue growth🔗 Connect with Tyler & GrowthX:Tyler on LinkedIn: search “Tyler Pavlas GrowthX” - https://www.linkedin.com/in/tyler-pavlas/Email: tyler@growthx.aiGrowthX: https://growthx.ai/AI-Led Growth community: https://ailedgrowth.com/If you got value from this episode, hit Like, Subscribe, and drop a comment with your favorite insight.And if you’re a Founding AE or founder in the trenches, tell us:👉 What’s been the hardest part of the founder → AE handoff for you? 💪 Try FollowUp for FreeBack-to-back demos and follow-ups piling up? FollowUp instantly generates personalized Digital Sales Rooms from your sales calls—built for Founding AEs to move deals forward and enable champions to sell internally. Try it for free: https://www.gofollowup.ai/

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. 💪 Try FollowUp for FreeBack-to-back demos and follow-ups piling up? FollowUp instantly generates personalized Digital Sales Rooms from your sales calls—built for Founding AEs to move deals forward and enable champions to sell internally. Try it for free: https://www.gofollowup.ai/

EP 12 - 3x Founding AE: Why 70 % of First Sales Hires Fail (and How to Get Yours Right)

Most founders massively underestimate how hard it is to make their first sales hire. The data says ~70% of first sales hires don’t make it to 12 months — and for early-stage startups, that mistake can be fatal.In this episode of The Founding AE podcast, Justin Dorfman sits down with Ian Illig, 3x Founding AE and Co-Founder of Stompbox, to break down exactly how to de-risk your first sales hire and set them up to win.Ian shares his journey from first employee at a dorm-room startup to multiple successful exits, and how that led him to helping founders build a repeatable sales system before they hand the baton to a Founding AE.You’ll learn:When you’re actually ready to hire your first AEThe 3-part readiness checklist: clear ICP, real paying customers, and a founder calendar that’s full of sellingWho to hire (and who to avoid)Why “big logo” reps from Salesforce/HubSpot often flame out in early-stage rolesWhy early-career, coachable reps with grit usually outperform “superstars” with RolodexesHow to think about industry experience the right wayHow to interview and evaluate a Founding AESimple live exercises to test coachability and humilityRed flags vs green flags for the first sales hire in a startupOnboarding that actually worksWhy overloading them on product knowledge kills momentumHow to structure a 30 / 60 / 90-day planThe scorecard system: inputs, outputs, and outcomes so you’re not flying blindSales mindset in 2025 and beyondWhy the “spray and pray” AI-powered outbound arms race actually makes high-integrity, relationship-driven sellers stand out even moreWhy the people who hate “icky sales” are often the ones who should absolutely be in salesIf you’re:A technical or non-sales founder about to make your first AE hireA founder who’s already 0-for-1, 0-for-2, or 0-for-3 on sales hiresOr an aspiring Founding AE who wants to understand what great looks like…this episode will give you a practical, honest playbook for getting it right.🔗 Resources mentioned:Stompbox's Sales Hiring Checklist: https://stompbox.io/before-you-hire-the-sales-checklist-for-founders-2/Stompbox's Sales Activity Scorecard: https://stompbox.io/free-weekly-scorecard-template/Connect with Ian on LinkedIn: https://www.linkedin.com/in/ian-illig-2326b139/👉 If you enjoyed this episode:Hit Subscribe for more deep dives on the Founding AE roleDrop a comment with your biggest takeaway or your first-sales-hire war storyShare this with a founder who’s about to hire their first AE (and needs to hear it before they do)💪 Try FollowUp for FreeBack-to-back demos and follow-ups piling up? FollowUp by AssetMule instantly generates personalized Digital Sales Rooms from your sales calls—built for Founding AEs to move deals forward and enable champions to sell internally. Try it for free: https://www.gofollowup.ai/

EP 11 - How to Succeed as a Founding AE: Red Flags, Green Flags & Real Advice

What does it really take to be the first sales hire at a startup?In this episode of The Founding AE Podcast, Justin Dorfman sits down with Anda Willett, a seasoned B2B SaaS seller with 15+ years experience selling into local government, higher education, and nonprofit markets — and most recently, a true Founding AE at an early-stage startup.Anda breaks down the reality of building GTM from zero: the chaos, the creativity, the red flags, the green flags — and why she fell in love with the founding AE role.If you're a founder hiring your first AE, or a seller thinking about becoming one, this episode is mandatory listening.⭐ What We Cover:🔥 The Founding AE Role — What Makes It DifferentWhy the first sales hire is NOT a traditional AEThe emotional highs, lows, and ownership mindsetWhy you must see your impact immediately (the good, bad, and ugly)🔥 Red Flags & Green Flags When Evaluating a StartupWhen NOT to take a founding AE jobHow to identify whether a founder is actually ready for salesWhy a handful of truly happy early customers matters more than anything🔥 30/60/90 Expectations for Founding AEsWhat realistic expectations look likeWhy you shouldn’t promise revenue in 30 daysHow to show traction early without closing deals🔥 Creative Prospecting That Cuts Through NoiseAnda shares her 3 favorite unconventional strategies:Handwritten letters that stand outHigh-impact 60-second Loom videosUsing podcasts + community to spark conversations🔥 The Must-Have Tools for Your First 90 DaysCRM or no CRM? (HubSpot vs. everything else)Core systems you need before anything fancyWhat tools can wait until later💬 Connect With Anda WillettLinkedIn: https://www.linkedin.com/in/awillettEmail: anda.willet@gmail.com🎙️ About The Founding AE PodcastEvery week, we go deep with early-stage sellers, founders, and GTM leaders who have built companies from zero — and learn how they did it. If you're the first seller at a startup (or want to be), you're in the right place.💪 Try FollowUp for FreeBack-to-back demos and follow-ups piling up? FollowUp by AssetMule instantly generates personalized Digital Sales Rooms from your sales calls—built for Founding AEs to move deals forward and enable champions to sell internally. Try it for free: https://www.gofollowup.ai/