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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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