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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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