5 stops, 5 lessons: what we learned from a season of SaaS events

This spring, we packed our bags and hit the road.

ChartMogul’s goals for the start of the 2025 event season were simple. Spend time with customers. Listen more than we talk. Learn what’s shaping SaaS teams today. And walk away better informed; not just about trends, but about the people and ideas behind them.

We joined five events across Europe and North America: SaaStanak, SaaSiest, Stripe Sessions, SaaStock USA, and SaaStr Annual. What we got back was a clearer sense of what matters right now in SaaS, how different regions operate, and how much value comes from showing up in person.

If you’re planning your 2026 events calendar, here’s what stood out.

SaaStanak: grit and honesty on the Croatian coast

Sun. Sea. SaaS. This was the first stop on our spring tour, and it delivered.

3 standout themes from SaaStanak (+ a bonus):

HonestyOne through-line reverberated throughout the well-curated agenda: unfiltered honesty. There was very little posturing, which led to the kind of meaningful conversations and advice that turn into lasting friendships.

FocusOn your vision for the business and product. On honing your craft. On caring for yourself as much as your business. SaaStanak founders don’t suffer shiny object syndrome, meaning I didn’t get stuck in silly AI conversations.

GritFounders in this region often build with fewer resources and more determination. If you’re looking for inspiration on the tough aspects of building, come to SaaStanak. This crowd isn’t backing down.

BonusThe bonus theme is Enterprising Energy. It’s hard to put into words, but the team behind SaaStanak just gets what it means to do good business. From coordinating rides for speakers to genuinely thanking sponsors, and including families… It’s clear Leonard Eldić and the team care. You all make people want to do business with you. Consider that my testimonial.

SaaSiest: ambitious and tight-knit Nordic ecosystem

This was my second year attending. We chose to return because the Nordics are still underrepresented in ChartMogul’s customer base, and I want to understand why. What does it actually take to build trust and credibility with SaaS founders and revenue leaders in this region?

Back from SaaSiest in Malmö, where the energy was unmistakably Nordic: crisp, ambitious, and full of substance.

Stop 2 on ChartMogul’s spring road tour brought 3 different themes into focus:

Diversity that stands outAt the Women in SaaS networking event, I was struck by the depth of female leadership talent. We simply don’t see this level of representation in Germany. It was both energizing and refreshing. I was pleased to have the opportunity to learn more about what these businesses are doing to foster this kind of representation.

A close-knit, local-first ecosystemHeading into the event, I was curious whether the market’s perceived insularity was real. It is. Many teams prefer local tools and prioritize relationships within the region when evaluating vendors. Earning trust here requires more time and deeper context. One of my major goals this year is to build out our understanding of regional markets.

Ambition backed by strong executionThe product stories and growth milestones shared throughout the conference were impressive. SaaSiest on stage has an insane production quality. And kudos to those speakers because those are BIG stages. These brave founders are aiming high, but they’re doing it with quiet confidence and sharp focus. There’s a lot of big SaaS success stories (and potential customers) here.

Stripe Sessions: a serious but welcoming vibe

Megan Tennant had the opportunity to attend Stripe Sessions in person, and we wanted to highlight some key takeaways. Stripe Sessions is the least SaaS-y event on our agenda this spring. 

One of our goals in attending was to learn more about the latest innovations in billing and payments, and to test how the positioning of ChartMogul CRM resonates in a Stripe-centric ecosystem. The event delivered on both fronts.

Here are 3 themes that stood out:

Big ideasThis was the largest Stripe Sessions to date, and the energy at the Moscone Center reflected it. From AI to stablecoins to payment efficiency, the conversations were rich and forward-looking. With keynotes from Mark Zuckerberg, Sir Jony Ive, and the Mayor of San Francisco, it was clear everyone showed up to absorb bold ideas and explore what’s next in tech.

CraftTalks centered around Stripe’s product, billing optimization, and revenue growth strategies. A standout moment was the design-focused fireside chat with Sir Jony Ive, who reminded us of the connection between mindset and the work we produce:

“My state of mind and how I am in my practice, ultimately is going to be embodied in the work.”

Serious, but welcoming vibeThis wasn’t the kind of conference where you’d see flashy booth costumes or gimmicks. The tone was more polished and professional, but still friendly. Conversations sparked easily over coffee lines, lunch tables, or chance meetings in the garden.

SaaStock USA: A scrappy crowd, ready to build

Austin gave SaaStock a new energy – less polish, more hustle. Compared to its European counterpart, the US version attracted early-stage founders and builders, looking for traction.

Our takeaways from SaaStock Austin: 

Early-stage companies are hungry for communityMost of the people we met were in the early innings. They wanted tactical advice, peer validation, and tools that scale with them, not over them.

Fewer big names, more buildersThe sponsor floor was filled with growth-stage startups. The mix created a strong signal that smaller companies are showing up and looking to compete.

AI still dominates, but there’s nuanceYes, AI was everywhere on the agenda. But the conversations were more grounded. People talked about implementation, not just opportunity.

A moment that stuck

We finally got the chance to team up with the Pavilion crew for a pre-SaaStock coworking day and happy hour. MRR Mule, anyone? The event featured a fireside chat with Jeff Perry, CRO of Carta. The room may have been cozy, but the conversations were excellent. 

SaaStr Annual: A fresh approach to showing up

Our final stop was a familiar one. SaaStr Annual brought in a classic mix — founders, GTM teams, and public company execs. But this year we skipped the booth, and it changed everything.

What we learned:

More flexibility, deeper conversationsWithout a booth, we weren’t tied to shifts or badge scan quotas. That freedom gave us more time to go deep in 1:1 conversations, whether at side events or quiet corners.

Fewer leads, but higher qualityOur contact count was smaller than in previous years, but the conversations were more memorable. People weren’t just scanning us in passing. They were choosing to connect.

The event landscape is shiftingWe noticed some subtle shifts: fewer large booths, more consolidated sponsor areas, and a lot of attendees flying solo or in lean teams. The best SaaS businesses know there’s a lot to build, which means being thoughtful about how to spend time and energy.

A moment that stuck

At the co-hosted breakfast with our integration partner Chargebee, we reconnected with churned customers, active users, and new prospects; all in one room. We also made a few partner connections that could open doors down the line. It was a reminder that ROI sometimes comes from conversations you didn’t plan for.

What we’re taking forward

Across five cities, a few consistent themes emerged.

In-person still mattersPeople want to be heard. They want to talk to people, not just brands. The fastest way to build credibility is still to show up with curiosity, not a pitch.

Regional context is everythingWhat works in Berlin won’t land the same way in San Francisco. Local tools, cultural dynamics, and buying processes vary more than you think.

The quality of connection beats the quantityThe conversations we had will shape how we sell, market, and support moving forward.

Where we’re heading next

We’ll be back on the road later this year. In the meantime, we’re putting what we’ve learned into practice across product, content, and how we engage with customers.

Want to follow along? Each week, we curate the best insights, growth strategies and emerging trends in B2B SaaS. Sign up for our SaaS roundup.