Summits & Events
Bringing together talented leaders across our network
Mainsail's annual summits and events work to bring together leaders from across our portfolio companies to network, share ideas, and brainstorm strategies to efficiently grow their software companies.
The 2026 CEO Summit brought together Founders, CEOs, and Board Directors to Scottsdale for two full days of candid conversations on leading vertical software companies through transformation, embedding AI, and positioning for the next stage of growth. Attendees participated in engaging case studies and small group discussions while building connections that extended beyond the sessions.
- - Lessons in vertical market and AI transformation
- - Building a corporate, product, and data strategy as your differentiator
- - Elevating customer engagement and education as a strategic, non-data moat
- - Owning your ecosystem through data and distribution
- - Using add-on M&A to accelerate growth and expand TAM
- - Building the right team for an AI-native environment
- - Leading under pressure with clarity and trust
The 2026 Product & Tech Summit brought together product and technology leaders from across our portfolio for two days in Denver. The theme, Leading Software Companies Through the AI Shift, centered on how teams can move from experimentation to execution as AI reshapes how software is built, priced, and delivered.
- - A growth mindset as the foundation for AI adoption
- - Accelerating innovation: redesigning workflows and doubling output
- - Building a GTM motion as fast as your product
- - Outcomes-based pricing in the age of AI
- - Activating your data flywheel as a competitive moat
Payment leaders from across our portfolio came together in Denver for the 2026 FinTech Summit, with data strategy as the driving focus. Every session was a working session — real operators sharing lived experiences and tackling shared problems.
- - Turning non-monetized payments volume into revenue
- - Using AI to deepen customer and data intelligence
- - Closing the feedback-to-product loop
- - Marketing payments as a product rather than a feature
- - Building features for workflow gravity
- - Building your data strategy
Mainsail hosted our annual Growth Summit in Chicago, bringing together sales, marketing, and customer experience leaders from across our portfolio. The theme, Building the AI-Driven Revenue Team, centered on how AI can accelerate growth and help go-to-market teams find greater efficiency and scale. The Growth Summit also celebrated standout GTM achievements from 2025 and concluded with a poker tournament that put everyone’s competitive instincts to work.
- - Becoming an AI-first leader
- - Building a 2026 strategic plan, capacity model, budget, and unlocking new pipeline sources
- - Driving accountability and scale within teams
- - AI use cases and a hackathon to identify new customer insights
- - How to successfully rebrand a business
- - M&A integration and cross-sell best practices
Finance leaders from across the Mainsail portfolio gathered in Chicago to exchange ideas, discuss opportunities and address challenges they face today. The agenda blended strategy with connection, from CFO roundtables and interactive panel discussions to a citywide scavenger hunt and enjoying Chicago deep dish pizza.
- - AI use cases and adoption in finance
- - Budgeting best practices
- - Legal considerations for embedding AI into products
- - RevOps and its evolution
- - Data lake design and implementation
People leaders from across the Mainsail portfolio gathered in Austin to explore how attracting, retaining, and developing talent drives scalable growth. The summit sparked practical conversations on how to build strong, high-performing teams.
- - Leveraging AI to streamline and optimize HR operations
- - Creating equity programs to boost engagement and recognition
- - Understanding how talent strategy can impact company valuation
- - Building communication skills through conversational intelligence
Fintech, Go-to-Market, and Product leaders from Mainsail’s portfolio gathered in Denver to explore how software companies can expand revenue opportunities through compelling payments and fintech offerings.
- - Implementing AI to drive adoption and feature utility
- - Accelerating time to value and boosting customer utilization
- - Exploring fintech strategies to strengthen competitive moats
Founders, CEOs, Board Directors, and Mainsailors enjoyed two days in Scottsdale discussing strategies to embrace AI, drive customer-centric innovation, and scale effectively in a fast-changing market. Attendees participated in engaging case studies and small group conversations while building valuable connections from the ballroom to the pickleball court, hiking trail and golf course, and back.
- - Case Studies on AI-Driven Products and Productivity Gains
- - Strategic Leadership & an AI-First Mentality
- - Customer-Centric Innovation
- - Market Conditions & Ways to Respond
- - What’s Working to Drive Growth
- - Lessons Learned Post-Recap/Exit
We value the collective brainpower of the leaders across our portfolio companies and celebrate opportunities to get together, expand our knowledge banks, and have fun!
