#209: Leading from Both Sides of the Table as a PE-Backed SaaS CEO - Steve Oriola

Summary of #209: Leading from Both Sides of the Table as a PE-Backed SaaS CEO - Steve Oriola

by Greg Head

53m•August 14, 2026
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Overview of #209: Leading from Both Sides of the Table as a PE-Backed SaaS CEO — Steve Oriola

Greg Head talks with Steve Oriola, CEO of Unbounce (which now includes Insightly), about what it’s like to run a private equity-backed SaaS business through major market change. The conversation focuses on the differences between founder-led startups and PE-owned operating companies, how to balance investor expectations with employee realities, and how AI and agentic software are reshaping go-to-market and product strategy in MarTech.

Key Topics Discussed

Unbounce + Insightly integration

  • Steve joined Unbounce in January 2024.
  • Unbounce acquired Insightly in July 2024.
  • The combined company now operates with roughly 200 employees.
  • The business serves mid-market and smaller customers with:
    • a landing page / conversion optimization platform
    • a sales-oriented CRM
    • project management capabilities tied to the sale process

Operating a PE-backed SaaS company

  • Steve explains the biggest shift from founder-led life to PE ownership:
    • the investors own the company
    • decisions are more finance-driven and faster-moving
    • the CEO must mediate between human concerns and hard business realities
  • He emphasizes empathy and transparency with employees, especially when explaining finance concepts like EBITDA and ARR.
  • He notes that private equity firms tend to be control-oriented and more decisive than venture capital firms.

AI and agentic software transformation

  • The company is actively rebuilding around AI and agentic capabilities.
  • Steve says software development velocity has increased, but commercialization still requires go-to-market planning, customer context, and operational change.
  • He believes SaaS is moving toward a new model:
    • “software as a service” becoming more like “service as software”
    • more managed services and forward-deployed engineering
    • human-in-the-loop support for governance and implementation
  • Unbounce is also using hackathons to surface new product ideas and has commercialized multiple ideas from them.

Change management inside an established software company

  • Steve says scaling and integrating legacy SaaS businesses often requires getting smaller and more focused before expanding again.
  • He believes reducing scope can be emotionally difficult for employees because it feels like “taking work away,” but it’s often necessary for clarity and competitiveness.
  • The company rewrote its values after the acquisition to create one shared culture.

Working with founders after acquisition

  • The original Unbounce founders remain actively involved:
    • the founding CEO is chairman
    • other founders serve as board observers and active advisors
  • Steve values their continued involvement because they bring product insight, brand credibility, and founder energy.
  • He also warns that founders often need help adjusting to the pace, structure, and governance of a larger PE-backed business.

Steve Oriola’s Main Takeaways

1. The CEO role is partly about managing both sides of the table

  • A strong CEO must understand investor logic while still protecting the business and the people in it.
  • The best CEOs can translate between the investor mindset and the employee/customer reality.

2. PE ownership is not just about optimization anymore

  • In today’s SaaS market, PE firms can’t rely solely on go-to-market fixes.
  • The underlying product and business model may need redesign, especially in the AI era.

3. AI lowers the cost of building, not the cost of building a business

  • Code can be produced faster now, but commercialization, governance, and customer adoption still require work.
  • The real challenge is redesigning the whole operating model around AI.

4. Founders can succeed in larger systems if they adapt

  • Founders who stay involved after a sale can learn a lot from structured operating environments.
  • But they need to accept that a larger company has process, pacing, and accountability that differ from startup life.

5. Focus beats sprawl

  • Steve advises founders to stay lean, avoid unnecessary complexity, and resist over-expansion before product-market fit is solid.

Advice for Founders Thinking About Selling to PE

  • Delay fundraising as long as possible to preserve control and optionality.
  • Stay lean and focused until product-market fit is clear.
  • Be careful with equity grants; make sure early allocations vest and are truly earned.
  • Know your customer deeply and keep talking to them constantly.
  • Expect PE to value metrics, discipline, and returns more than startup-style experimentation.
  • If you stay involved after an acquisition, be realistic about the fact that the buyer now owns the company and has the final say.

Notable Insight

“You’re really dealing with humans, so you’re the mediator between humanity and cold-hearted business.”

That line captures the core tension of Steve’s perspective: a CEO must balance empathy, execution, investor pressure, and market change all at once.

Bottom Line

This episode is a practical look at what happens when a seasoned SaaS operator takes over a PE-backed company and rebuilds it for an AI-first market. Steve Oriola’s perspective is especially useful for founders who may someday sell to private equity, stay involved afterward, or simply want to understand how modern SaaS companies evolve once they move beyond startup mode.