Welcome to the Fortium Partners Insights blog, where we highlight the strategic voices shaping the future of technology leadership. Today, we’re talking with James Simmons, a Fortium Partners CTO Partner with more than 15 years of experience leading teams, defining strategy, and delivering SaaS platforms in some of the most regulated industries out there. He’s also a founder and a strong advocate for what AI makes possible in the C-suite.
Fortium CEO, Burke Autrey, sat down with James to dig into his perspective on where executive leadership and technology are headed.
Burke Autrey: James, thanks for joining. Your bio points to a unique mix of deep technical chops and executive leadership. You’ve said you’re “coding again” after 15 years in senior roles. What does that shift mean for today’s executives and their organizations?
James Simmons: Great to be here, Burke. The short answer: AI has blown open the gates. For nearly two decades I was full-time in leadership mode as a CTO, CEO, and/or a board advisor. I stayed close to the tech, but I hadn’t written a meaningful line of code in 15 years. Six months ago, that changed. I’m building again.
The real shift here is that things which were impossible for a time-strapped executive a year ago are suddenly doable - and not just doable, but almost absurdly easy. This isn’t really about executives becoming coders. It’s about the walls between disciplines dissolving. The model of “deep specialist only” is giving way to adaptive generalists who can span strategy, product, and technology. That changes how C-level leaders execute, because now they can directly touch the work instead of always working through layers.
Burke Autrey: That idea of adaptive generalists feels timely. How does rolling up your sleeves technically translate into innovation and decision-making advantages?
James Simmons: The biggest change is the speed and cost of experimentation. I can have an idea on Tuesday and test it myself by Thursday. In the old model, you needed a team, a formal proof-of-concept, and often tens of thousands of dollars to even get to a “maybe.” Now, I can validate a concept in a couple of days.
What matters most is not just speed - it’s access. AI lowers the barrier to testing by an order of magnitude and changes what ideas even make it onto the table. I’ve greenlit projects with real funding precisely because I could prove the idea worked upfront. Under the old system, those ideas never would’ve survived the cost-benefit hurdle. The whole funnel of innovation opens up when proof gets cheap.
Burke Autrey: That’s a big shift. Given the demands on an executive’s time, how do you find capacity for that kind of hands-on work? Is AI part of the answer here too?
James Simmons: 100%. The only reason I have room for this is because AI gives me back half my day. I’ve leaned into an “AI-first” mindset - whether it’s drafting content, structuring ideas, or just clearing admin overhead.
That shift frees up hours for building and experimenting, which I genuinely enjoy. The fun matters more than people think - it creates energy. And that energy shows up in how you lead.
Burke Autrey: Shifting to your client work: how do you, as a Fortium Partner, bring these benefits into boardrooms and leadership teams?
James Simmons: My role is helping companies move faster and smarter through technology. Sometimes that’s as an advisor; other times it’s stepping in as a fractional executive to lead strategy and delivery. The buckets look like this:
AI integration – embedding AI into products and processes, whether customer-facing or behind the curtain.
Scaling platforms and teams – especially for SaaS, FinTech, ConstrucTech, or investor-backed companies needing to level up quickly.
Product development and launch – making sure the right product gets built, the right way, on the right timeline.
M&A support – diligence, integration, roll-ups. I’ve led companies through acquisition, so I know both the playbook and the pitfalls.
Organizational transformation – taking companies from services to SaaS, or from one-time sales to subscription models.
The key point here is that I don’t just hand over slide decks. I pair strategy with hands-on execution so the advice actually sticks.
Burke Autrey: For the CEOs and C-suite leaders reading this, what’s one actionable takeaway you’d emphasize as they navigate the current technology landscape?
James Simmons: Be ready to pivot - and do it based on data, not ego. A lot of the limits we hit are self-imposed. You can have a well-built plan, but if the data shows the model isn’t working, you’ve got to be willing to rewrite the story. I had that experience at heyLIME. We launched with a consumer gaming focus, gained traction, but the economics didn’t hold. The hard call was pivoting away from the original vision.
The lesson: don’t fall in love with your assumptions (CYA - Check Your Assumptions). Keep asking what’s really working, and if the answer requires a hard turn, make it. That willingness is a survival skill. And today, leaders need to think of AI not as a buzzword, but as a personal and organizational force multiplier. The companies that lean in early will shape the curve. Those that wait will be playing catch-up.
Burke Autrey: James, thank you. This has been a fascinating discussion—practical, candid, and forward-looking.
Are you a CEO or C-level executive looking to drive growth, navigate complex transformations, or build a more agile and innovative technology organization? Fortium Partners brings proven technology leaders like James Simmons to your executive team, offering advisory, fractional, and interim CIO, CTO, and CISO services tailored to your unique needs.
Contact us today to discover how our "leadership-as-a-service" model can help you unlock your strategic advantage.
James Simmons is a highly accomplished technology-focused business leader with over 15 years of experience specializing in the strategy, development, launch, and operation of SaaS platforms across regulated, mission-critical, and high-security industries (B2B, B2C, and B2G). He possesses a proven ability to bring order to chaos by building high-performing teams, defining and executing strategic roadmaps, and delivering solutions to Fortune 500 clients and millions of users. His expertise spans diverse sectors, including aerospace and defense, intelligence, logistics, and legal services. Mr. Simmons has presented on technology topics at major conferences like SXSW and to government leaders, and holds a BS in Computer Science from Harvey Mudd College.