XO Summit is an annual CEO retreat hosted by High Alpha.
As a startup CEO and founder, it’s important to, occasionally, step back from the hustle and bustle of startup life and spend quality time with peers going through similar challenges and experiences. While it’s a cliche to say that leading a company is lonely, the statement holds true. We believe connection, camaraderie, and programming that sparks inspiration isn’t just important for founders, but critical.
This year, our portfolio CEOS and founders gathered together for XO Summit 2025 in the mountains of Wanship, Utah, to reconnect and listen to speakers covering topics from M&A to GTM, brand, and storytelling. Let's dive into the highlights.
Your Story Is Your Strategy
If You Confuse, You’ll Lose
No matter the stage of your company, one thing’s certain: if you confuse, you’ll lose. In Donald Miller’s discussion, the New York Times bestselling author and CEO of StoryBrand emphasized the importance of clear and compelling storytelling in capturing audience attention and driving marketing success. Effective marketing shouldn’t make people think too hard — instead, it should organize the message for easy comprehension and motivate purchases through clear calls to action.
Your Company Is Not the Hero
The session also explored the workings of the human brain in marketing, noting that your brain is designed to conserve energy and focus on survival. Complicated explanations are often rejected by the brain, leading to disengagement. In other words, you have to capture attention or risk losing your audience to daydreaming and survival thoughts like, “what am I going to eat for lunch today?”
The solution: storytelling.
Most companies make themselves the hero when it comes to storytelling. In reality, the customer should be the hero and your product should act as the guide. In the structured storytelling approach, the hero (your customer) should have a clear need or problem that a guide (your product) can provide a plan for, that calls the hero to action, and that ultimately results in success.
Lead from Where You Are
Impact matters more than titles. During a fireside chat with High Alpha Co-Founder and Managing Partner Scott Dorsey and BambooHR CEO Brad Rencher, a central theme was focused on a BambooHR core value that empowers employees to lead from one's current position.
Brad and Scott talked about leadership development, with expectations for leaders to demonstrate functional excellence, authentic connection to the mission, and the ability to influence and inspire. The importance of authenticity and vulnerability in leadership cannot be overstated — the best leaders are consistent across interactions and recognize talent regardless of title or style.
Mastering the Game of M&A
Jeff Chang, Co-President at Qatalyst Partners presented on the current M&A landscape for SaaS companies, focusing on market multiples and trends. Some key takeaways:
- General trading multiple for software companies is around 6x, similar to levels from 2013-2017, with high-growth companies trading at 10x. Infrastructure software (trading at 7.5x) often has more pricing power than application software (trading at 5.5x).
- Despite a decline in software revenue, cash flow has increased as companies prioritize efficiency.
- Growth is still important, and commands a premium in the market.
- In 2025, 75% of deals are being led by strategic acquirers, with new buyers like Snowflake and ServiceNow entering the market.
Finally, Jeff discussed the importance of hiring a banker with knowledge of the company and strong relationships with decision-makers, the significance of due diligence and legal considerations in M&A transactions, and reiterated that founders should try their best to manage emotions and expectations during the M&A process to achieve the best outcomes.
From Conviction to Category Creation
Initially focused on returns management, Narvar Founder Amit Sharma shared the story of how the company expanded to a full logistics platform, emphasizing personalized customer options, seamless business integration, and third-party integrations.
The session also touched on leadership experiences and strategies for dealing with investor feedback, particularly regarding the perception of the company's offerings as mere features rather than a platform. Perseverance and conviction in the product’s value were critical to Narvar’s success. One example of how this manifested was the focus on female buyers and their pain points, a group that holds extraordinary economic buying power but is often overlooked.
GTM: Scale Beyond Sales
Databricks President of Global Field Operations Andy Kofoid shared learnings from growing large organizations: Databricks has experienced significant growth, reaching 8,000 employees with billions of dollars in revenue.
During the fireside chat with High Alpha Co-Founder and Partner Mike Fitzgerald, Andy shared sales structures, compensation strategy, and the shift from a subscription based model to usage-based pricing. The session also dove deep into building “A” level teams, expectation setting within your sales organization, and ramp times for employees.
The Mindset of a Champion
The ups and downs of leading a startup closely mirror the ups and downs of competing at the highest level. In keeping with the location of XO Summit 2025, Olympic skier Kaylin Richardson shared her story with our CEOs and founders, highlighting her path from Minnesota to the Olympics. She emphasized the importance of setting clear goals, which requires accountability and courage, and touched on managing risks while training at high speeds, facing physical challenges such as crashes and injuries, and how to maintain perspective during difficult periods.
Onward
Ultimately, XO Summit provides a space for founders to not only gain practical insights from industry leaders, but from each other. It's a time and place for CEOs and founders to create meaningful moments of connection, and to leave a bit more energized, optimistic, and inspired.
For us, it’s a privilege to be able to bring together such a remarkable group of founders, thought-leaders, and guests for such an impactful event.
