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/