SaaStr Podcast #025: Anthony Kennada, VP of Marketing @ Gainsight On Why Events Are So Important for Startup Marketing

Startup marketing has a funny way of making founders believe the internet is the whole battlefield. Launch the website. Post on LinkedIn. Run ads. Pray to the algorithmic gods. Repeat until the budget starts coughing dramatically in the corner.

But in SaaStr Podcast #025, Anthony Kennada, then the founding VP of Marketing at Gainsight, made a case that still feels remarkably fresh: for startups, especially B2B SaaS startups, events are not just “nice brand moments.” They can become category-building machines, customer-learning labs, partner ecosystems, sales accelerators, and community campfires all rolled into one very expensive badge printer.

The episode focused on Kennada’s work at Gainsight, where he helped lead marketing across demand generation, brand marketing, and the creation of Pulse, the Customer Success community event that became closely tied to Gainsight’s rise. What makes the story valuable is not merely that Gainsight hosted an event. Lots of companies host events. Some even remember to order coffee. The lesson is that Gainsight used events to make an emerging business category feel real, urgent, and human.

That is the heart of this article: why events matter so much for startup marketing, what SaaS teams can learn from Anthony Kennada’s approach, and how founders can use events even without a giant budget, a celebrity keynote, or a fog machine that says “Series B.”

Why This SaaStr Podcast Episode Still Matters

SaaStr Podcast #025 arrived during a period when B2B SaaS was maturing fast. Startups were no longer judged only by product features. They were judged by their ability to create markets, educate buyers, build trust, and move upmarket. In that environment, marketing could not simply be the department that made brochures look less tragic. It had to create belief.

Anthony Kennada’s perspective was especially interesting because Gainsight was not selling into a market everyone already understood. Customer Success, now a familiar SaaS term, was still developing as a formal business discipline. Gainsight had to do more than explain its product. It had to help executives understand why retention, expansion, customer health, and post-sale experience deserved boardroom attention.

That is a much harder job than selling software in an existing category. When a company enters a crowded market, the message is often, “We are better.” When a startup creates or defines a category, the message begins earlier: “This problem matters. This role matters. This community matters. You are not alone.”

Events are unusually powerful for that kind of work because they turn an abstract idea into a room full of people nodding at the same problem. A category stops being a slide deck and starts looking like a movement.

Gainsight, Pulse, and the Power of Community-Led Marketing

Gainsight’s Pulse event is a textbook example of community-led startup marketing. Instead of treating the event as a standard user conference, the smarter play was to build a gathering for the broader Customer Success profession. That distinction matters.

A user conference says, “Come learn about our product.” A category conference says, “Come shape the future of your profession.” The second one is much more compelling, especially for people who are trying to win internal budget, define their team’s value, or convince leadership that their work is not just support wearing a blazer.

Pulse gave Customer Success leaders a shared stage, shared vocabulary, and shared identity. That helped Gainsight become associated not only with software, but with the entire movement around customer retention and growth. This is the kind of brand positioning that ads struggle to buy because it is built through participation, repetition, and trust.

Events Turn Customers Into a Market Signal

For startups, customer logos are useful. Testimonials are useful. Case studies are useful. But a room full of customers, prospects, partners, analysts, and operators is a different kind of proof. It tells the market, “Something is happening here.”

That signal is especially valuable when a startup is early in a new category. Buyers may wonder whether the problem is big enough. Investors may wonder whether the market is real. Prospects may wonder whether they are too early. An event answers those doubts in a physical, social way. When hundreds or thousands of people gather around the same topic, the category gains weight.

In other words, an event is not just a marketing activity. It is market theater in the best sense: a live demonstration that the conversation is bigger than one vendor.

Why Events Work So Well for Startup Marketing

Events work because they compress trust. A prospect who ignores ten emails may have a meaningful conversation after one good breakout session. A customer who feels mildly engaged may become an advocate after meeting peers with the same challenges. A partner who has been “circling back” since the Bronze Age may finally commit after seeing the energy around the brand.

Digital marketing is excellent for reach, targeting, and measurement. But events add something that dashboards cannot fully capture: emotional momentum. People remember who helped them meet the right person, understand a hard problem, or feel like they belonged in a professional community.

1. Events Build Trust Faster Than Content Alone

Content can educate, but events create direct experience. When a founder speaks honestly on stage, when customers share practical lessons, or when attendees ask unfiltered questions, the brand becomes more believable. The company is no longer just a logo online. It has a voice, a face, and hopefully a registration desk that does not collapse under pressure.

For startup marketing, this trust advantage is huge. Younger companies often lack the reputation of established competitors. Events give them a chance to borrow credibility from customers, partners, speakers, and the quality of the conversation they host.

2. Events Help Startups Educate the Market

When buyers do not fully understand a category, education becomes marketing. Gainsight’s work around Customer Success shows how valuable that can be. The company was not only explaining features; it was helping professionals understand a new way to operate recurring revenue businesses.

Events are ideal for education because they support multiple formats: keynotes for vision, panels for social proof, workshops for implementation, roundtables for peer learning, and hallway conversations for everything people are too polite to say into a microphone.

3. Events Create Content That Keeps Working

A well-run startup event should not end when the lights turn off. Sessions can become blog posts, short videos, podcast clips, email campaigns, sales enablement assets, social content, customer stories, and executive thought leadership. One strong event can fuel months of content if the team plans ahead.

This is where many startups underuse events. They treat the event as a single day instead of a content engine. The smarter approach is to capture the best ideas before, during, and after the event, then redistribute them across the funnel. Your keynote should not retire immediately after lunch. It deserves a second career.

4. Events Strengthen Sales and Marketing Alignment

Startup sales teams love warm conversations. Marketing teams love proving influence. Events can make both groups temporarily stop side-eyeing each other in the revenue meeting.

Before an event, sales can identify target accounts, invite key prospects, and schedule meetings. During the event, reps can deepen relationships in a natural environment. After the event, marketing can segment follow-up based on attendance, session interest, engagement, and account priority.

The result is not just “lead generation.” It is relationship acceleration. That matters in B2B SaaS, where buying committees are complex and trust is built across multiple touchpoints.

What Anthony Kennada’s Event Playbook Teaches Startups

The big lesson from Kennada’s Gainsight era is that events should serve a strategic narrative. Pulse was not random. It connected directly to Gainsight’s mission, category, customers, and long-term brand. That is why it mattered.

Startups often make the mistake of asking, “Should we host an event?” A better question is, “What market conversation do we need to own?” If the event does not help answer that, it may become an expensive party with lanyards.

Start With the Community, Not the Company

The strongest startup events are built around audience pain, not vendor ego. If every session is basically “Here is why our product is amazing,” attendees will detect the sales pitch faster than a teenager detects slow Wi-Fi.

A community-first event asks better questions: What problems are our buyers trying to solve? What do they need to explain to their bosses? What peers do they want to meet? What frameworks would help them do their jobs better? What topics are they already debating privately?

When the event helps the audience become smarter, better connected, and more confident, the brand earns attention instead of demanding it.

Make the Event Bigger Than Your Product

Gainsight’s Pulse became powerful because it represented Customer Success as a profession, not merely Gainsight as a platform. That approach made room for customers, experts, partners, and even broader industry voices.

For startups, this is a useful principle: the narrower your product pitch, the smaller your event feels. The bigger your market thesis, the more people can see themselves in it.

A cybersecurity startup might host an event about trust in AI workflows. A fintech startup might host a roundtable on operational resilience. A developer tools company might create a community series around engineering productivity. The product still matters, but it sits inside a larger conversation.

Design for Belonging

People attend events for content, but they remember how the event made them feel. Did they meet useful peers? Did they feel included? Did sessions respect their intelligence? Did the agenda solve real problems? Did the coffee taste like coffee, or like a printer cartridge with ambition?

Belonging is not soft. It is strategic. When people feel part of a community, they come back, tell others, share content, and become more open to the brand behind the experience.

How Startups Can Use Events Without a Massive Budget

Not every startup can build the next Pulse on day one. That is fine. Trying to copy a major conference too early can drain resources and produce a sad ballroom full of empty chairs, which is basically a haunted house for marketers.

Early-stage startups should think in smaller, sharper formats.

Executive Dinners

An executive dinner with ten carefully selected people can outperform a large generic event. The goal is not scale; it is relevance. Invite people who share a real business challenge. Keep the sales pitch light. Use thoughtful prompts. Capture themes for future content and product messaging.

Customer Roundtables

Roundtables are excellent for learning. They reveal customer language, objections, priorities, and emerging trends. They also help customers feel heard. For startups still refining positioning, that feedback is gold with appetizers.

Virtual Workshops

Virtual events still matter when they are practical. A workshop that helps attendees solve a specific problem is far more valuable than a vague webinar titled “Innovation in the Modern Enterprise,” which sounds like it was generated by a bored conference committee.

Partner-Led Field Events

Partnering with complementary companies can reduce cost and increase reach. The key is alignment. The audience should make sense for everyone involved, and the topic should not feel like four vendors taped their pitch decks together.

Measuring Event ROI Without Losing Your Mind

Events are powerful, but they also create measurement anxiety. Leadership wants numbers. Finance wants justification. Sales wants pipeline. Marketing wants attribution that does not require detective work and three emergency spreadsheets.

The best approach is to define success before the event. Different event types should have different goals. A customer advisory dinner may be measured by retention insights and executive engagement. A field event may be measured by target-account meetings and pipeline influence. A large conference may be measured by community growth, content production, brand lift, partner engagement, and revenue impact.

Useful metrics include target-account attendance, meetings booked, opportunity creation, pipeline influenced, customer expansion conversations, speaker/customer advocacy, content views after the event, social engagement, and post-event survey quality. The trick is to avoid pretending one metric explains everything.

Events influence people in layered ways. Someone may attend a session, read the recap, forward a clip, talk to a peer, and only then request a demo. That does not mean the event failed attribution. It means humans are not vending machines.

Events as Category Creation Engines

Anthony Kennada’s broader marketing philosophy is often associated with category creation, and events are one of the strongest tools for that work. A new category needs language, stories, rituals, proof, and champions. Events can create all five.

Language emerges through keynotes and frameworks. Stories come from customers and practitioners. Rituals form through annual gatherings and shared traditions. Proof appears when respected companies participate. Champions emerge when attendees begin repeating the message in their own organizations.

This is why events can be so valuable for startups trying to change how buyers think. They do not just generate leads; they generate consensus. And consensus is what turns a “new idea” into a budget line.

Common Event Marketing Mistakes Startups Should Avoid

Mistake 1: Making the Event Too Sales-Heavy

Attendees can tolerate some product discussion, especially if they are customers or active buyers. But if the entire agenda feels like a commercial, trust drops fast. Teach first. Sell second. Brag somewhere near the end, and only if you have earned it.

Mistake 2: Inviting Everyone

A great event is not always a big event. Startups should prioritize the right people over the most people. A room of qualified decision-makers, practitioners, and advocates beats a giant crowd that came only for free snacks and hotel Wi-Fi.

Mistake 3: Forgetting Post-Event Follow-Up

The event is not the finish line. The follow-up is where much of the value becomes visible. Segment attendees. Personalize outreach. Share relevant content. Ask for feedback. Connect people who should know each other. Turn the event into an ongoing relationship, not a calendar memory.

Mistake 4: Underinvesting in Experience

Experience does not always mean expensive production. It means thoughtful design. Clear signage, useful sessions, smooth check-in, good moderation, and intentional networking can make a modest event feel premium. Meanwhile, a huge event with confusing logistics can make attendees question their life choices by 10:17 a.m.

Practical Event Strategy for SaaS Startups

For a SaaS startup inspired by SaaStr Podcast #025, a simple event strategy might look like this:

• Define the market conversation: Choose the problem or category your company wants to lead.
• Identify the audience: Decide whether the event serves executives, operators, users, partners, or a mix.
• Select the right format: Use dinners, workshops, webinars, roundtables, or conferences based on stage and budget.
• Recruit credible voices: Customers, practitioners, and experts often carry more trust than internal speakers alone.
• Plan content capture: Record sessions, collect insights, interview attendees, and repurpose the best material.
• Connect sales early: Build target-account lists and meeting strategies before the event begins.
• Measure multiple outcomes: Track pipeline, engagement, learning, content, and community growth.

This approach keeps the event tied to strategy instead of vibes. Vibes are nice. Strategy pays invoices.

Additional Experiences and Lessons Related to Startup Event Marketing

One of the most useful experiences a startup team can have is watching how buyers behave when they are not trapped inside a sales call. Events reveal the market in motion. You hear the phrases prospects actually use. You notice which topics make people lean forward. You see which objections appear repeatedly. You learn who influences whom. That kind of intelligence is difficult to get from analytics alone.

For example, imagine a SaaS startup selling a platform for customer onboarding. Online campaigns may show that “reduce churn” gets clicks, but a roundtable might reveal that the real emotional pain is different: customer teams are exhausted because every onboarding process feels custom, chaotic, and impossible to scale. That insight can reshape messaging, product packaging, sales discovery, and future content. The event becomes a research tool disguised as a professional gathering.

Another important lesson is that events create internal alignment. When product, marketing, sales, customer success, and executives all attend the same customer conversations, the company develops a shared understanding of the market. This is underrated. Many startups struggle because each department has its own version of the customer. Events put everyone in the same room with reality, and reality is a very effective meeting facilitator.

Events also help startups discover advocates. The best advocates are not always the biggest customers. Sometimes they are the most thoughtful practitioners, the most generous community members, or the people who explain your category better than your own homepage. A smart event team pays attention to these voices. Invite them to speak. Feature their stories. Ask for feedback. Help them build their own professional credibility. Advocacy works best when it is mutual, not extractive.

There is also a confidence-building effect. Early startup teams often wonder whether their message is landing. A strong event provides immediate feedback. If the room is engaged, questions are sharp, and attendees stay after sessions to continue the conversation, the team knows it is touching a real nerve. If the room is quiet enough to hear the projector fan reconsider its career, the message may need work. Painful? Yes. Useful? Extremely.

Finally, events teach patience. The ROI may not appear instantly. A prospect may attend a dinner in March, join a webinar in June, introduce a colleague in September, and become an opportunity in November. That does not make the event weak. It means the event planted trust early in a long buying journey. Startup marketers should track outcomes carefully, but they should also understand that the most valuable relationships are often built over time.

The experience behind SaaStr Podcast #025 remains relevant because it reminds startups that marketing is not only about capturing existing demand. Sometimes the bigger opportunity is to gather people around a problem, give them language, create belonging, and help them see a future they want to join. That is what great events do. They make the market feel less like a spreadsheet and more like a movement.

Conclusion

SaaStr Podcast #025 with Anthony Kennada is more than a throwback episode from the SaaS archives. It is a reminder that startup marketing becomes far more powerful when it moves beyond campaigns and starts building community. Gainsight’s use of Pulse showed how events can help define a category, educate buyers, elevate customers, and create a durable brand advantage.

For modern startups, the lesson is clear: do not treat events as decoration. Treat them as strategic assets. Whether you host a ten-person dinner, a tactical workshop, a customer summit, or a full-scale conference, the goal is the same. Bring the right people together around a meaningful problem. Help them learn. Help them connect. Help them believe that your company understands where the market is going.

That is why events are so important for startup marketing. They create the one thing every startup needs and no automation tool can fully manufacture: trust at human speed.

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