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 Mainsail Talent Summit brought together people leaders from across the portfolio for candid conversations on what defines great leaders today, how software companies are putting AI to work in practice, and how people teams can build their own AI workflows right now, no engineering bottleneck involved. Every conversation was grounded in experience from operators navigating the same challenges. In between sessions, the group took a breath at Sundance: hiking the trails, tooling leather journals, riding horses, and ziplining.
- - Leading people through uncertainty around AI and building a culture where adoption can take hold
- - Traits of great entrepreneurial leaders and the team dynamics that define high-growth companies
- - Guidance for People leaders to help drive AI enablement across their organizations
- - Working sessions to build practical AI agents and workflows for people teams
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
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!
