About
Al Mays
I think like a CEO. I speak the language of engineering. I fix what I find.
Blue Bear Advisory · Denver, CO
What Makes This Different
I don't just see the technology stack. I see the business.
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.
The operating system I bring to every engagement wasn't designed in a consulting practice. It was built across twenty years of being accountable for outcomes, through the successes and the hard times. You learn the most when things aren't working: when an integration is harder than anyone projected, when an engineering organization can't ship and customers are losing confidence, when a product portfolio built through acquisition has no shared strategy and the teams are pulling in different directions. The frameworks and operating models I use today came from those moments, from having to figure out what was actually wrong and build the tools to fix it. That's a different kind of credibility than presenting a methodology designed in a classroom. And it's why my work doesn't stop at the assessment. Fixing what I find means working with board members who think in multiples, CEOs navigating uncertainty, engineering teams spread across continents, and customers who have lost confidence. Meeting people where they are and bringing clarity to conversations that have been going in circles is what turns an assessment into actual change.
Twenty years. Every side of the table.
Outcomes from operator roles and advisory engagements combined. The cross-business lens doesn’t distinguish between them.
10X
Revenue growth at a VC-backed startup
2.5X
Revenue growth at a PE-backed platform through M&A
30+ pts
EBITDA improvement
50%
Cloud cost reduction through FinOps and modernization
200+
People managed across global distributed teams
$30M
Technology budget managed
18 → 6 mo
Integration timeline compression
60% → 5%
Change failure rate transformation
15+
M&A engagements across buy-side, sell-side, and direct integration, as CPTO of a seller, CPTO of a buyer, and as an advisor
4
Industry verticals: digital experience & content, e-commerce & data, healthcare technology, and automotive technology
10
SaaS product markets including DXP, CMS, DAM, CMP, customer journey analytics, e-commerce & search, privacy & consent, healthcare administration, healthcare data & analytics, and automotive retail technology
Where It Comes From
20+ years of product and technology leadership across every side of the table: 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 independent advisor on buy-side and sell-side diligence. I've sold directly to customers as a sales engineer, owned the relationship as an executive sponsor in good times and bad, and 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, from PE board rooms to front line engineering teams across the US, Europe, and Asia.
About the name
Blue Bear was my son's first stuffed animal. Still in his room today, still showing up in family photos, still a quiet code name in conversations. When it came time to name the practice, I thought about Doug Cutting naming Hadoop after his son's stuffed yellow elephant, and how the best names in tech often have personal roots. This one does too.
How the practice is structured
Blue Bear is intentionally a small practice. I take on a limited number of active engagements at a time so each client gets the senior attention they're paying for.
When an engagement calls for parallel workstreams, specialized depth, or capacity beyond what one advisor should responsibly carry, I bring in trusted collaborators from a network built over twenty years of operating and advisory work: former SaaS executives, PE operating partners, and outsourcing delivery partners with direct PE, M&A, and post-merger integration experience. People I've worked with and delivered alongside. The cross-business lens stays consistent. The bench scales when the work demands it.
Voices
What colleagues, clients, and leadership teams say about working with me.
“Often you find strong CPO/CTOs that have amazing technical acumen but lose sight of the ultimate goal of being a successful business, or ones that have strong business acumen but are challenged in gaining the full trust of their teams. Al brings both to everything he does.”
David Fuoto
Software Leader | Strategic Growth | CCO | M&A Integration Executive
“Well-run ELTs require leaders to take the functional hat off and be a business leader with no borders. Al was a leading example of this, day in and day out. His area required, as it frequently does, hard decisions and complete control of large spans. Al was frequently first to the table with hard solutions that supported the broader business.”
Aaron Whiting
Software Operating Executive | M&A Integration | Business Architecture
“Al navigated multiple M&A situations we faced. Acquisitions can be stressful, particularly for those concerned about job security or disruptive changes. Al always took these concerns seriously, acknowledging the fears of employees while still executing the necessary changes. His ability to balance empathy with the need to drive the business forward was nothing short of extraordinary.”
Andreas Knoor
Global Head of Product | Building AI product teams at scale
“Al played a key role in transforming a struggling business via some very difficult decisions while simultaneously keeping key members engaged and productive, something not all leaders can claim.”
Jodi Reynoso
HR Executive | Private Equity | SaaS B2B | Global M&A
“One of Al’s greatest strengths is his rare combination of deep technical expertise and sharp business acumen. He never lost sight of the ultimate goal: building a successful business while ensuring that our technology strategy aligned with the company’s needs.”
Christoph Feddersen
Product & Tech Leader | Driving Innovation and Growth in Tech Industries