The 7 Secrets of Success for SaaS CEOs with Randy Wootton CEO of Maxio

Ryan Staley interviews Randy Wootton who shares his incredible journey from the U.S. Navy to working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing. Randy reveals the seven secrets of success for SaaS CEOs, offering invaluable insights on navigating the challenges of scaling a business.

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  • Randy Wootton transitioned from a successful career in the U.S. Navy and working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing.
  • As a CEO, Randy emphasizes the importance of delivering shareholder value, establishing a winning strategy, shaping company values and standards, building an effective executive team, managing the board and investors, allocating capital strategically, and investing in your personal growth.
  • Randy discusses the challenges of selling to CFOs compared to CMOs, highlighting the need for a different go-to-market motion that involves bringing in influencers and references, as CFOs tend to be more introverted and rely heavily on relationships when making purchase decisions.
  • Maxio uses the McKinsey Horizon Model to allocate funds for current and future growth, dedicating resources to core business (Horizon 1), near-term opportunities like payments (Horizon 2), and long-term game-changing initiatives (Horizon 3).
  • Randy believes that AI will significantly impact go-to-market strategies, with boards expecting companies to incorporate AI efficiency assumptions into their fiscal year 2025 planning, and he advises businesses to start experimenting with AI tools now to stay ahead of the curve.
  • To navigate the challenges of being a CEO, Randy recommends finding a mentor who has been in a similar position, working with a coach to improve interpersonal effectiveness, joining peer groups like EO or YPO, and cultivating a personal advisory board for support and guidance.
  • Randy highlights the importance of being a system of record and having differentiated data that can be leveraged with AI to create intelligent engines that offer benchmarks and insights to help customers run their businesses more effectively.
  • By sharing his experience co-founding the VetForce platform at Salesforce, which empowers military veterans, Randy demonstrates his commitment to making a positive social impact alongside his professional achievements.


“I am there to deliver shareholder value. That’s primarily driven by delivering the results.”

“One of the things when I became CEO, the first time was I wanted a mentor, someone who had been in the same context.”

“I think for my own career growth, I had reached this inflection point where I thought, gosh, the patterns that I’ve seen in this scenarios, would it apply to a different vertical in this case, selling to the CFO?”

“Unless you’re absolutely crushing it and everyone’s gonna make a whole bunch of money, like there is [something] everyone starts to revert to it’s like Maslow’s hierarchy of need. They’re all nice until it becomes, okay, how are we going to carve up the pie?”

“I think anyone who’s truly appreciative of what’s happened in their life will also recognize how much luck has played and connections, and we’ll be willing to give back to other folks.”

Ryan Staley

Founder and CEO

Whale Boss

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: