SaaS Backwards Episode 196 - The SaaS Opportunity Hidden Inside Services

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

In this episode, we explore how a professional services business can uncover, validate, and fund a SaaS opportunity.

Dillon Okner, founding partner of The Oak Group, joins SaaS Backwards to share the story behind SiteRise, a SaaS platform built for retail construction, development, and site planning teams. After years of working on retail development at Apple, Tesla, and Enjoy Technology, Dillon kept seeing the same operational problem: growing teams were managing high-stakes store openings with fragmented documents, inconsistent naming conventions, scattered reports, and no single source of truth.

Rather than raising venture capital immediately, Dillon and his team bootstrapped SiteRise through their services business. That approach gave them time to validate the product, stay close to customer pain, and build a stronger foundation before scaling sales.

We also discuss how services and software can reinforce each other. The Oak Group’s consulting work exposes real customer problems, while SiteRise gives clients a structured system for document management, project reporting, location data, and planning.

Dillon explains why the messy “Google Sheets to scale” phase is such an important trigger for SaaS founders to recognize. When teams start creating reports from other reports, managing separate data sets, and using inconsistent nomenclature, the business may be ready for a purpose-built platform.

The conversation also covers go-to-market lessons for early-stage SaaS companies, including relationship-led outbound, conference strategy, LinkedIn Sales Navigator, founder-led sales, and the transition to hiring a dedicated account executive.

Key takeaways:

• How to identify SaaS opportunities inside repeated services work
• Why bootstrapping through services can reduce pressure and improve product-market fit
• How SiteRise helps retail teams centralize construction documents, project reporting, and location planning
• Why inconsistent data, naming, and reporting are signs a market may be ready for software
• How in-person events and creative lead capture can support early SaaS growth
• What changes when a company moves beyond founder-led sales

Prefer to watch? Check out this episode's video here. 

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting