JMI 2026 AI Product & Technology Roundtable

The question facing every software company right now is not whether to adopt AI — it’s whether leadership can move fast enough to stay ahead of their competition. That tension was at the center of JMI’s AI Product & Technology Roundtable, where more than 220 executive, product, technology, legal, and fintech leaders from across the portfolio gathered in Washington, D.C. for two days of candid conversation in June.

The through-line across every session: AI transformation is ultimately a leadership challenge, not just a technology initiative. Discussion focused on how leaders can harness AI to transform their businesses and teams — building better products, accelerating execution, and creating measurable value for customers. It requires executives to set a clear ambition, model new ways of working, build organizational confidence, and create the conditions for teams to experiment quickly while staying focused on the outcomes that matter most.

JMI’s Harry Gruner and TalentScape Partners’ Rodgers Palmer opened by connecting AI urgency to the fundamentals of great leadership. Drawing on the DARE framework — the four behaviors most strongly linked to high-performing CEOs: decisiveness, engagement, adaptability, and reliable delivery – their message was pointed: AI does not replace these behaviors, it raises the bar on them. The next phase will put a premium on faster decision-making, continuous reinvention, and a more hands-on “player-coach” model.

Marty Cagan, founder of Silicon Valley Product Group, delivered the opening keynote with a challenge that reframed the rest of the roundtable: AI can dramatically increase speed, but velocity only creates value when teams are focused on the right problems. The companies that benefit most will not simply move faster; they will pair speed with the product discipline to decide what is worth building, why it matters, and how it will improve outcomes for customers.

In his fireside chat with JMI’s Eric de Jager and Russ Wakelin, Marty sharpened the point on CEO accountability. Sponsoring AI transformation from a distance isn’t enough. The CEO has to model it. Leaders must define the outcomes that matter, give teams the context and authority to make better decisions, and align the organization around customer impact rather than output alone.

Attendees then moved into role-specific tracks, each one digging into what AI transformation actually looks like at the functional level:

• CEOs tackled how AI shifts companies from delivering software to doing work on behalf of customers, how to benchmark product velocity, and how to create protected space for new bets.
• Product leaders explored the changing cost-to-value equation, implications for pricing and packaging, and the move toward a faster, higher-value, AI-powered product development lifecycle.
• Technology leaders dug into reinventing the software development lifecycle, rearchitecting platforms, treating specs as a core software asset, and securing agentic systems by design.
• Legal leaders addressed AI-first M&A, compressed diligence timelines, evolving IP and data obligations, and the new security baseline for agentic workflows.
• Fintech leaders discussed how to scale in a fast-moving market while uncovering hidden economics across the payments stack.

The most important takeaway was also the simplest: the constraint is not the technology. It is the organization’s ability to absorb change.

AI changes how work gets done, what great performance looks like, and how quickly teams can test, learn, and ship. The companies that pull ahead will do more than deploy AI tools. They will redesign how decisions are made, how teams operate, and how value reaches the customer.

Thank you to every attendee, presenter, and track leader who made this Roundtable both thought-provoking and energizing. We are grateful to work alongside such a talented group of operators. We’ll keep the conversation going across the portfolio and hold each other accountable for turning it into action.

JMI’s next Roundtable will focus on Go-to-Market and take place September 2-3 in Washington D.C.

Disclaimer: This post is for informational purposes only and reflects general observations from JMI Equity’s 2026 AI Product and Tech Roundtable. References to AI initiatives and third-party presenters are provided for illustrative and educational purposes only and should not be interpreted as research, investment advice, or any investment recommendation. AI involves evolving opportunities and risks, including technological change, competitive dynamics, and regulatory developments. Past trends and forward-looking statements are not guarantees of future outcomes.