Al Mays

Most technology advisors can tell you what's happening inside the engineering organization. That's the easy part. What I do is connect it to everything around it: the commercial model, the financial structure, the go-to-market motion, the customer dynamics, and the investment thesis.

That perspective isn't something I developed later in my career. It's where I started. My first job in technology was in a call center, writing code on an IVR self-service platform where I grew to be accountable for both the technology and the business outcome it served. I sat on the budgeting committee before I had a title that suggested I should. Technology and business have never been separate for me because they never were from the beginning.

I've sat in board meetings translating technology decisions into financial consequences, worked with sales leadership on how product capabilities shape the pipeline, partnered with finance to restructure cost models that were quietly destroying margin, and then walked into the engineering room and led the team through execution. That range isn't a nice-to-have. It's the difference between a technology assessment that lives in a slide deck and one that changes the trajectory of a company.

But seeing the business clearly is only half of it. The other half is getting people to move. Fixing what I find means working with board members who think in multiples, CEOs navigating uncertainty, engineering teams spread across continents and cultures, and customers who have lost confidence. The ability to meet people where they are and bring clarity to conversations that have been going in circles is what turns an assessment into actual change.

Twenty-plus years across every side of PE-backed SaaS: as a CPTO managing 200 people across globally distributed teams and complex multi-product portfolios, as the buyer leading M&A integrations, as the target company navigating an acquisition, and as an advisor on buy-side and sell-side diligence through Crosslake Technologies and Brainware Consulting.

I've sold directly to customers as a sales engineer. I've looked customers in the face as an executive sponsor, in good times and bad. I've led the professional services teams responsible for delivering on what sales promised. I've been the continuity through CEO and CFO transitions, holding the institutional knowledge of the business when leadership turned over. And I've built trust across every level and background, from PE board rooms to front-line engineering teams across the US, Europe, and India.

I’ve also made the hard call about my own role, recognizing when a company’s evolution meant it needed different leadership alignment, raising it directly with the board, and stepping away knowing it was the right thing for the business even when it wasn’t the easy thing personally.