in review
As we look to the year ahead, we’re energized by the possibilities of this next cycle and grateful for the partners who continue to build it with us.
2025 marked an inflection point for growth-stage technology. After a few years of correction and recalibration, the market regained its balance. Management teams with focused leadership innovated and accelerated revenue growth, all while preserving strong unit economics. And although the generative AI era technically began in 2022, this was the year it blossomed into a Golden Age of AI that is reshaping how companies operate and how markets form.
At the same time, the ecosystem continued to feel the aftershocks of the past cycle with an increasing number of companies remaining private, fewer exits, less liquidity flowing back to LPs, and growing concern about the contours of an AI-driven bubble. The paradox of 2025 was that both momentum and imbalance defined the landscape.
For us, that combination sparked extraordinary opportunity. The pipeline of compelling investments grew deeper and more diverse. Our portfolio companies delivered meaningful improvements across nearly every performance metric. The persistence of illiquidity only reinforced the strengths of our strategy. Through it all, we stayed focused and executed with discipline, resilience, and conviction in our long-term strategy.
New Investments
This year’s new investments reflect a clear throughline: visionary teams building the infrastructure, intelligence, and tools that will define the next decade of innovation. From AI systems reshaping how humans work to platforms reimagining data, cloud, health, and financial operations, these companies share a common ambition: solving deeply complex problems with elegant, scalable technology.
Portfolio Impact
This year has been marked by extraordinary momentum across the portfolio, as our companies shaped markets, forged major partnerships, and achieved milestone valuations.
Across transformative acquisitions, multibillion-dollar raises, and strategic alliances with industry giants, these leaders not only advanced their own missions, but they helped redefine what’s possible across healthcare, software, defense, fintech, and consumer services. The headlines below offer a snapshot of the scale and breadth of their impact.
Community as Capital
The Circle continued to serve as a real-time intelligence engine with a window into how the strongest growth-stage companies are operating, adapting, and scaling.
AI reshaped every function and forced leaders to rethink work itself. GTM teams retooled for efficiency and precision. Across conversations, a sharper picture emerged of the capabilities that truly separate durable companies from drifting ones.
Trend #1
AI Adoption Became the Defining Competitive Differentiator
Companies that embedded AI into core workflows saw measurable productivity gains, more confident planning, and a flattening of the traditional headcount curve. These teams just weren’t experimenting, they were redesigning cost structures.
Trend #2
GTM Efficiency Rose as the Central Lever for Sustainable Growth
With customer acquisition costs rising and buyers self-educating deeper into the funnel, GTM efficiency became the dominant growth narrative. The strongest teams restructured motions around hybrid human + AI models, standardized their sales processes, and tightened RevOps ownership.
Trend #3
Cyber + AI Threats Pushed Risk Management to the Board Level
The risk landscape shifted meaningfully. Cybercrime accelerated with AI-powered automation, ransomware moved from operational disruption to reputational blackmail, and unmanaged internal AI usage introduced new vulnerabilities. These forces pushed cybersecurity out of IT and squarely into the CFO and board domains.
Trend #4
Leadership Strength Emerged as the Key Signal of Scaling Companies
Across dozens of conversations from CFO influence to budgeting discipline to board alignment, one theme continually surfaced: executives at the highest-performing companies influence across functions, forecast with rigor, and aren’t afraid to push back when the stakes require it.
More than any single trend, 2025 affirmed the power of peer learning, The Circle’s true superpower.












Top Content of 2025
What to know about refresh strategies, valuation volatility, and managing investor and employee expectations
Tactical examples for CFOs and finance teams to use today
Evolve from the budget holder to a cyber risk steward
What you need to know about the 2025 overhaul to maximize your tax savings
Video “show and tell” of practical ways to move beyond pilots and embed AI where it matters most
From us to you, may your 2026 be filled with growth, connection, and unshakable purpose.
Here’s to another year of supporting great companies and the visionary leaders building them.

Ken Loveless
Partner, Co-Founder

Mike Jung
Partner, Co-Founder

Mark Dempster
Founder, The Circle

Amy Aina
Investment Administration

Andrew Boston
Partner

Anthony Matusich
Chief Financial Officer

Avery Cannon
Chief Administrative Officer

Dominick Richiuso
Investor

Hannah Starbranch
Senior Content & Communications Manager

Kalee Gardella
Partner / Chief Community Officer, The Circle

Marilu Livermore
Partner/Chief Operations + Growth Officer

Nikki Tatalovich
Senior Manager, Events & Partnerships

Owen Van Arsdale
Partner

Ryan Morrison
Partner

Tyler Zengo
Investor























