EP 9 - Selling Services vs SaaS, the No Demo Playbook & When to Hire Your First AE

Sales isn’t “Wolf of Wall Street.” In this episode, Chris Taylor (Founding Sales Lead at New Charter Technologies) breaks down how he went from being skeptical about sales to leading zero-to-one teams—plus the big differences between selling IT/security services and pure SaaS. We dig into what replaces the “demo” in a services motion, how to know it’s time to hire, whether your first reps should be junior or senior, red flags for the early stage, and how to protect mental health while being a present parent and an effective operator.🎙 Host: Justin Dorfman https://www.linkedin.com/in/justindorfman87/👤 Guest: Chris Taylor https://www.linkedin.com/in/chris-taylor2What you’ll learnWhy services sales requires a deeper trust motion than SaaS—and how to earn itThe “no-demo” centerpiece: proofs, scope walkthroughs, and in-person trustA simple litmus test for when to build the sales team (repeatability over heroics)Hiring early reps: hunger + hands-on builders who can grow into leadersRed flags that scream “not a fit” for zero-to-onePractical boundaries for mental health, family, and performanceChapters00:00 Intro00:49 Chris’s path: Memphis to San Diego to startups & sales03:40 Flipping the script on sales (from apprehension to alignment)07:12 Services vs. SaaS: how the buyer’s mindset really differs10:38 The “No-Demo” Playbook: what you show when there’s no product demo14:55 When to build the team: repeatable process as the green light18:50 Who to hire first: junior vs. senior, and the true sweet spot21:27 Red flags for zero-to-one sellers23:12 Mental health, boundaries, and being a present parent27:45 Where to find Chris & wrap-up👍 If this helped, hit Like, Subscribe, and drop your biggest takeaway in the comments.🔔 New episodes weekly on founding sales, GTM, and leadership.💪 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/#FoundingAE #SalesLeadership #SaaS #ProfessionalServices #B2BSales #StartupLife #MentalHealth #Sales