A CRO who helped scale a company from its first dollar of revenue to a $500M+ acquisition joins Verticals for a practical conversation on sales, scale, and vertical AI.

In this episode, Luke Sophinos and Nic Poulos sit down with Martin Roth, former CRO of Levelset, where he built and scaled the sales organisation from day one through their acquisition by Procore.

We go deep on what actually changes as sales teams scale, the mistakes founders make as revenue grows, and how vertical AI is starting to reshape sales roles earlier than most teams expect.

This is an operator-level conversation grounded in lived experience, not theory.

We cover:

• What really changes when sales moves from early traction to scale

• Common mistakes founders make as revenue grows

• How sales roles and structure evolve over time

• Where vertical AI is genuinely changing sales workflows

• Where AI is overhyped, and what still requires humans

• Why incentives and structure matter more than tools

• What breaks first when growth accelerates

• How to think about scaling sales before problems appear

If you’re building or leading sales in vertical SaaS or vertical AI, this episode offers practical insight from someone who’s seen the full journey, from zero to exit.

New episodes drop every Wednesday.

00:00 – Intro: Verticals, sales, and vertical AI 01:20 – Introducing Martin Roth (CRO, Levelset → Procore acquisition) 04:00 – Joining at $0 revenue: what the early days really look like 07:30 – Early sales hires: what matters and what doesn’t 11:00 – When sales starts to break — and why it’s normal 15:00 – Scaling structure vs scaling headcount 18:30 – Founder-led sales vs professional sales leadership 22:30 – Incentives, quotas, and misaligned behaviour 26:30 – What changes as revenue grows from millions to scale 30:30 – Vertical AI enters sales: what’s actually useful today 34:30 – Where AI is overhyped in sales organisations 38:30 – Humans vs automation: what doesn’t get replaced 42:00 – Retention, expansion, and durable revenue 46:30 – Common mistakes founders make too late 50:30 – How to think about sales design before scaling 54:30 – Lessons from seeing the full arc, end to end 58:30 – Closing thoughts: building sales systems that last

A founder who sold his first company for $100M+ and now builds businesses-in-a-box joins Verticals for a deep, operator-level conversation on vertical software, services, and scale.

In this episode, Luke Sophinos and Nic Poulos sit down with Dan Friedman — founder of Thinkful (acquired by Chegg) and now co-founder of Bolton & Watt, an incubator launching vertical companies like Moxie (MedSpas) and Meadow Memorials (funeral homes).

We unpack what actually makes business-in-a-box work, why most attempts fail, and how vertical SaaS founders should think about services, software, and defensibility in an AI-driven world.

We cover:

• Why “business-in-a-box” only works when three conditions are true
• How Moxie became the “Stripe Atlas for MedSpas”
• Why assembling off-the-shelf tools first beat building software too early
• The real reason vertical SaaS founders under-capture wallet share
• Services as a wedge vs a moat — and when they break
• Retention math, percentage-of-revenue pricing, and ROI defensibility
• Why vertical focus matters more as OpenAI expands horizontally
• How to spot vertical opportunities founders consistently misjudge

If you’re building in vertical SaaS, vertical AI, or compound startups, this episode offers practical frameworks — not theory — from someone who’s built, sold, and scaled repeatedly.

New episodes drop every Wednesday.

Episode Chapters / Minutes

00:00 – Intro: Verticals, vertical tech & AI 01:30 – Introducing Dan Friedman (Thinkful → Chegg, Bolton & Watt) 04:30 – Why Dan loves years 1–3 of building more than scaling orgs 07:00 – What Bolton & Watt actually is (incubator vs venture studio) 10:30 – How Moxie started: spotting unmet demand in MedSpas 14:00 – “Business-in-a-box” explained — and why most versions fail 18:00 – The three conditions required for business-in-a-box to work 22:30 – Why Moxie started with off-the-shelf software (not custom) 26:00 – Launch → Run → Grow: the Moxie operating model 30:00 – Percentage-of-revenue pricing & retention realities 34:30 – Churn, early failures, and moving up-market 38:30 – Why ROI calculators matter more than features 42:00 – Services + software: wedge vs defensibility 47:00 – Why most vertical SaaS founders underuse services 51:30 – The role of scale economics and national purchasing power 55:00 – Vertical focus vs horizontal AI expansion 58:30 – What founders consistently get wrong when choosing markets 1:02:00 – Closing thoughts: building durable vertical businesses

A VC and a Founder intellectually spar on Vertical Tech & AI, covering the latest news, unpacking in-depth business strategies, and interviewing world-class leaders in the space. New episodes drop every Wednesday.

In this episode, Luke Sophinos and Nic Poulos sit down with Sam Youssef, Founder & CEO of Valsoft, one of the largest vertical SaaS aggregators in the world, with 130+ acquisitions, 3,000+ employees, and ~$750M in revenue. Sam breaks down how Valsoft built a Berkshire Hathaway, style software platform, what actually drives value creation post-acquisition, and how AI is reshaping vertical markets from the inside out.

We cover:

- How Valsoft scaled from a single hotel software acquisition to 130+ vertical SaaS companies

- Why small, rational verticals outperform “big TAM” markets for aggregation

- The real drivers of post-acquisition growth: payments, AI labs, global delivery centers, and product expansion

- How to evaluate founders, integrity, and culture before buying a business

- Why AI will accelerate value creation for systems of record, and destroy vendors with too much tech debt

- What most people misunderstand about the threat of vertical AI upstarts

- How Valsoft sources deals across 25+ countries with 100+ people in M&A

- What founders should know before selling to an aggregator (and when to raise their hand) Whether you’re building in vertical SaaS, vertical AI, private equity, or exploring aggregation models, this episode gives you a masterclass in buying, scaling, and compounding durable software assets