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Guest: Dillon Okner, Founding Partner of The Oak Group / SiteRise

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In this episode, we look at how a services business can become the proving ground for a SaaS opportunity.

Dillon Okner, founding partner of The Oak Group and creator of SiteRise, joins us to talk about building software from the inside of a professional services business. SiteRise was born from repeated problems Dillon saw while helping retail brands manage construction, store openings, document control, reporting, and cross-functional planning.

We dig into why Dillon chose to bootstrap the SaaS product through services revenue instead of raising venture capital, how his team identified product-market fit, and why messy spreadsheets, inconsistent file naming, and disconnected reports are often signs that a market is ready for software.

Dillon also shares what is working in SiteRise’s go-to-market motion, including outbound, conferences, relationship-based selling, LinkedIn Sales Navigator, and a creative “headshot-led growth” tactic that turned trade show engagement into product interaction.

Key takeaways:

• How services can reveal repeatable SaaS opportunities
• Why bootstrapping can protect product focus
• What breaks when teams scale with spreadsheets and disconnected reports
• How better construction and retail development data can support boardroom-level planning
• Why founder-led sales eventually needs operational support

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Guest: Tim Schumacher, Co-Founder of saas.group

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In the AI era, code alone no longer drives SaaS value the way it once did.

In this episode of SaaS Backwards, we sit down with Tim Schumacher, co-founder of saas.group, to explore how AI is changing what buyers value in SaaS businesses and why that shift is forcing founders to rethink exits. We get into why code has become easier to recreate, while customer loyalty, proprietary data, strong products, and defensible market positions are becoming even more important.

We also unpack the new urgency AI is creating for founders. For some, AI is opening up real operational upside and making growth more efficient. For others, it raises a harder question: will this business stay differentiated in a market where software is easier to rebuild and replicate?

Along the way, we cover what makes a SaaS company attractive to acquirers, the mistakes founders make when preparing for an exit, and why bootstrapped founders should start with personal goals instead of trying to time the market.

Key takeaways

• Why code is losing value as a standalone SaaS asset
• What buyers value more now: data, customers, moats, and strong products
• How AI is influencing founder exit decisions
• What acquirers look for in bootstrapped SaaS businesses
• How founders can better prepare for a sale

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Guest: KG Charles-Harris, Founder & CEO of Quarrio

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The SaaS AI trap is believing fast answers are good enough when the real advantage comes from trustworthy, decision-grade intelligence.

In this episode of SaaS Backwards, Ken Lempit talks with KG Charles-Harris, founder and CEO of Quarrio, about why most AI tools fall short in enterprise environments where decisions need to be accurate, auditable, and actionable. KG explains the difference between probabilistic AI and deterministic AI, and why that distinction matters far more than most SaaS leaders realize.

They also explore why business users do not want more dashboards or more software to learn. They want answers to questions, delivered instantly, in a way they can trust. The conversation covers Quarrio’s long path to market, how enterprise trust is built through founder-led sales, and why compressing the cycle from data to decision to action may become one of the biggest competitive advantages in SaaS.

Key takeaways:

• Most enterprise AI tools are fast, but not reliable enough for decision-making
• Deterministic AI is better suited for auditable, enterprise-grade answers
• SaaS users want answers, not more dashboards or reporting delays
• Decision velocity may become a major competitive advantage
• Founder-led sales and trust are critical in early enterprise go-to-market

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Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup.

🔗 Get your free SaaS GTM Checkup