ServiceTitan’s Add-On Strategy That Went 0 to $100 million ARR in 5 years - Ershad Jamil

From 4 to 500 Reps: Building a High-Velocity Machine - Butch Hodson

In this episode of the Vertical SaaS GTM Playbook, Orbital’s Riley Soward sits down with Butch Hodson, VP of Sales at Sellfire and author of Sales Lab Scripting, to unpack the real playbook for hiring, onboarding, and coaching high-velocity sales teams. Butch has personally hired and trained over 400 sales reps and more than 10,000 sellers throughout his career — scaling teams from scrappy startups to well-oiled outbound machines. He shares what most companies get wrong about hiring, why role-plays beat resumes, how to structure the first 30 days of onboarding, and why the best managers spend 90% of their time coaching. This conversation is a masterclass in building a repeatable GTM engine that wins through people, process, and relentless coaching. KEY TAKEAWAYS 1. Hire for intangibles. Work ethic, coachability, growth mindset, and competitiveness are the non-negotiables for high-velocity sales. 2. Simulate, don’t interview. Role-plays, live scenarios, and homework assignments reveal more than traditional tell me about a time questions ever will. 3. Onboard with intention. Start with classroom learning, mix in live calling by week two, and certify every rep before they hit the floor. 4. Managers should coach 90% of the day. The best sales leaders are in the trenches listening to calls, giving feedback, and developing reps daily. 5. If you don’t believe in someone, don’t hire them. Once you put your name on a rep, it’s your job to make them succeed.

ServiceTitan’s Add-On Strategy That Went 0 to $100 million ARR in 5 years - Ershad Jamil

Going multi-product is the fastest way for vertical SaaS companies to grow ACV and retention, if done correctly. In this episode, Ershad Jamil (former CGO @ ServiceTitan) breaks down how his team evolved from a single platform to a portfolio of revenue drivers, including embedded payments, marketing automation, product catalog, and an early AI receptionist - scaling add-ons from $0 to $100M+ ARR in under five years. He walks through how to identify “share of wallet” opportunities, time the first add-on, and stand up a tiger team to ship an MVP without derailing core product. We get concrete on build vs. partner vs. buy, product packaging, and why CSM-led upsells often stall. Ershad also shares where teams go wrong, like choosing the wrong fintech partner or misforecasting adoption, and how to set the right KPIs so the motion compounds rather than distracts. KEY TAKEAWAYS 1. Start with share of wallet. Pull customer P&Ls, run surveys/webinars, and map where your users already spend (payments, financing, marketing, telecom, fleet). 2. Stand up a tiger team. One PM, 1–2 engineers, and a part-time GTM owner can ship an MVP and de-risk without detracting from core product. 3. Partner first on complex offerings. For payments, financing, and payroll, the right partner beats building from scratch. 4. Sell at the right moment. Activate payments during implementation to cement workflows; sell marketing automation once the customer is activated. 5. Don’t let CSMs carry upsells. Use commercially oriented AEs/SDRs for upsells and cross-sells, keep incentives and ownership aligned.

New Vertical Strategy That Took Podium from $1 Million to Hundreds of Millions ARR - Than Hancock

In this episode of the Vertical SaaS GTM Playbook, Than Hancock, CRO at Podium, breaks down the go-to-market strategy that helped the company grow from $1 million to over $200 million in ARR. Than joined Podium when it was still defining its first verticals and helped build the framework the company used to enter new markets with precision. He and Riley discuss how to spot when a vertical is tapped out, how to structure sales teams for focus without limiting growth, and what it takes to keep momentum after reaching $20M+ ARR. They also unpack how Podium decided which verticals to prioritize, how the team learned to say “no” to attractive but distracting opportunities, and what expansion looks like once you’ve already dominated a core market. If you’re leading GTM at a growing SaaS company, this episode offers a concrete look at how to scale through disciplined vertical execution. KEY TAKEAWAYS 1. Growth happens in phases, and each phase requires a different level of focus, structure, and discipline. 2. The right first vertical often emerges through iteration, not strategy decks. 3. Expanding into multiple verticals too early can stall momentum more than it accelerates it. 4. After $20M ARR, maintaining speed is about redefining focus, not chasing new markets. 5. There’s a clear point where stretching your ICP definition breaks positioning — learn to recognize it early. 6. Mature GTM teams find growth not by adding verticals, but by squeezing more from their existing TAM. 7. Even at $200M ARR, the best operators think about expansion as a system, not a one-time decision.

The 5 Biggest Pitfalls in Vertical SaaS GTM (and How to Avoid Them) - Ryan Heaphy

In this kickoff episode of The Vertical SaaS GTM Playbook, Riley Soward sits down with Ryan Heaphy to uncover the Top 5 go-to-market mistakes founders make when scaling vertical SaaS. They dive into why many early hires fail, how “free pilots” sabotage momentum, the nuances of SDR deployment, and how to approach enterprise deals without blowing your growth plan. Whether you're pre-product-market fit or scaling toward $10M+, this conversation is packed with lessons you can act on now. KEY TAKEAWAYS 1. Hire only when your playbook exists - Without a documented and repeatable sales process, new hires flounder. Ryan underscores that hiring early without structure is a top mistake. 2. Beware “free pilots” - While tempting, free pilots often attract uncommitted customers. They waste time and create false expectations. 3. SDR models aren’t universally good - The SDR approach can be powerful — but only when it fits the stage and business model. Misapplication drives dysfunction. 4. Don’t over-index on industry experience - Ryan challenges the notion that only industry veterans can sell in vertical SaaS. Grit, coachability, and sales instincts matter more. 5. Enterprise sales needs guardrails - Chasing big deals without a plan or clarity invites scope creep. He discusses how to de-risk enterprise moves and how a single well-executed deal can change your business trajectory. 6. Clarity and expectations are non-negotiable - Communication and alignment with enterprise buyers on scope, security, and commitment is critical to avoiding deal failure. https://www.youtube.com/@withorbital_gtm