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Strategic Communications Advisory For Visionary Founders
Actionable
Takeaways
Target meaningful pilots for clear ROI:
When piloting your solution, make sure it's run for long enough and with a large enough group to generate statistically significant data. This helps prove ROI and supports expansion.
Create a hybrid category to stand out:
If your solution overlaps multiple existing categories, clearly define your own niche. Jennifer calls Rising Team a "team performance platform," which merges learning, team-building, and engagement tools.
Leverage early adopters for growth:
Early champions, even from unexpected industries like banking, can help validate your product. Prove success with pilot data to secure long-term relationships and expand across the organization.
Adapt your offering to evolving market needs:
Rising Team initially focused on 1:1 manager tools but pivoted to team-focused solutions after discovering a larger demand for team-wide workshops and AI coaching.
Use psychological pain points to drive GTM:
Identify specific pain points (like low engagement or lack of budget for offsites) and tailor your marketing to offer immediate solutions, such as improving psychological safety or boosting team connections.
Conversation
Highlights
How Rising Team Rewrote Their Entire Go-to-Market Playbook in Under Six Months
February 2020 was an interesting time to hatch a startup idea. Jennifer Dulski, CEO and Founder of Rising Team, had just outlined her vision for a team performance platform when the world shifted beneath her feet. By April, she’d incorporated the company—right as the pandemic was forcing every organization to confront what she’d already identified as the core problem: building connected, engaged teams in an increasingly distributed world.
In a recent episode of Category Visionaries, Jennifer shared the tactical pivots and hard-won lessons that transformed Rising Team from a bootstrapped idea into a platform serving Google, Cisco, Airbnb, and other Fortune 500 companies. This isn’t a story about raising capital or hitting unicorn status. It’s about the specific go-to-market decisions that separated signal from noise.
The Product Pivot That Changed Everything
Most founders will tell you product-market fit is everything. What they won’t tell you is how brutally specific that fit needs to be. Rising Team’s original version focused on managers using assessments and tools one-on-one with each team member. It made logical sense—personalized attention, individual development, clear use cases.
It was also completely wrong.
“The very first version of the product was built mainly for managers to use one on one with each person on their team,” Jennifer explains. “And then what we realized and what was the huge unlock for the growth of the company was that doing this as a team would be more effective for two reasons. One is it saves a lot of time, you know, it’s much faster to get the whole team together in one meeting than to meet each person separately and the other is teams really crave this. They really want to know each other better.”
That second insight—that teams actively crave connection—became the foundation for everything that followed. The platform now helps leaders run interactive workshops without external facilitators, then channels those insights into a hyper-personalized AI coach that knows everything about the team. But the shift from individual to collective wasn’t just a product decision. It fundamentally changed how Rising Team went to market.
The Unlimited Pilot Trap
Here’s a mistake that costs startups months of momentum: optimizing for activation over value capture. Jennifer learned this the hard way.
“When I first started, I was like, we just need to get people to use this, whatever it takes,” she recalls. “And I offered unlimited teams for $1,500 for some short period of time, and a lot of people bought it, but then they didn’t really use it. There wasn’t really an incentive to get going with unlimited teams and so forth.”
The fix wasn’t intuitive. Rising Team didn’t shorten the pilot or lower the price. They went the opposite direction: twelve-month pilots with several hundred people, depending on company size. Why? Because that’s what generates statistically significant data to prove ROI.
“That’s what gives you statistically significant data to prove that it’s working,” Jennifer notes. “And that’s what then gives people the reason to see the ROI and continue expanding.”
This isn’t about being difficult or creating barriers. It’s about understanding what actually drives expansion decisions at enterprise companies. A CIO doesn’t expand based on anecdotal feedback from three teams. They expand based on data showing measurable improvements in engagement scores, manager effectiveness, and retention rates.
The Category Question Nobody Gets Right
Ask most founders about their category and you’ll get either a Wikipedia definition or a convoluted explanation that tries to be everything. Rising Team sits at the intersection of learning and development, team engagement, and team building—which sounds like a positioning nightmare.
“We call it a team performance platform. I believe that is in some ways a new category,” Jennifer explains. “The categories that we tend to compete against are either learning and development. So learning management systems, facilitators, they hire to do trainings or team engagement, measurement and movement, and then possibly a third category, which is kind of just pure team building.”
But here’s what makes their approach work: they don’t force the category on buyers. Instead, they capture demand from existing pain points—bad pulse scores, eliminated offsite budgets, disconnected remote teams—then explain why their offering delivers better outcomes than traditional solutions.
“We often come in through one of the, if you will, jobs to be done of things like my pulse scores came back and they’re really bad. I need help moving them or I no longer have an off site budget. How do I still keep my team connected?” Jennifer notes.
The land-and-expand motion happens organically. A CMO tries it with their team, sees results, and the data speaks for itself. Then someone moves to a different division and brings Rising Team with them. The platform found its first enterprise customer at Bank of Hawaii—not exactly the obvious early adopter for a tech startup, but someone who saw the potential and took the bet.
The Marketing Team of One
Silicon Valley loves to throw headcount at marketing. Rising Team took a different approach. Jennifer runs a go-to-market team of five or six people total, with just one dedicated to marketing.
“At a startup, our number one value at Rising Team is we’re all one team,” she explains. “And so the idea is when things need to be done, people are going to raise their hand and they’re going to jump in and do it.”
The strategy centers on rigorous growth experimentation—hypotheses, rapid testing, measurement. One recent surprise: adding more fields to their demo signup form to better route leads actually increased conversion rates, despite conventional wisdom suggesting friction kills conversions. Another experiment, a homepage chatbot everyone said they needed, hasn’t moved the needle at all yet.
The lesson isn’t that chatbots are bad or longer forms are good. It’s that you need to test your specific context rather than following playbooks. They focus marketing on functional and divisional leaders at large companies—the CMOs, CIOs, and VPs of engineering who have both budget and acute pain. These buyers find Rising Team when searching for solutions to specific problems like improving psychological safety.
The Remote Fundraising Reality
Jennifer raised all of Rising Team’s capital on Zoom. She met only one investor in person before closing the round. Some she still hasn’t met face-to-face. This isn’t a pandemic anomaly—it’s the new normal for startups that understand what really matters in investor selection.
“It’s not necessarily true that the people who give you the absolute highest valuation and the absolute most money will be the best investors over the long term,” she notes. This comes from someone who teaches scaling companies at Stanford’s business school, where she regularly sees case studies of founders who optimized for the wrong metrics in fundraising.
Mission alignment and long-term focus trump valuation bumps. It’s the kind of advice that sounds obvious until you’re sitting across from a term sheet with extra zeros on it.
The Three-to-Five-Year Bet
Rising Team’s vision extends beyond corporate teams. They’re expanding their AI offering to handle performance reviews and one-on-ones. They’re launching “mini kits”—ten to fifteen minute sessions designed for mobile devices—to reach hourly and frontline workers in factories, retail stores, and bank branches. They’re platformizing the entire system so others can build scalable interactive workshops.
“I believe that we can help every team on earth be more successful, more connected, and more engaged,” Jennifer says. “And we’re starting to see that happen already because we have Fortune 500 tech companies, but we also have school teachers and government agencies. I have, like the Massachusetts probation officers use Rising Team, and they all see the same kind of results.”
The data from Bank of Hawaii tells the story: higher engagement scores, improved manager effectiveness, and significant lifts in employee retention. These aren’t vanity metrics. They’re the business outcomes that justify expansion budgets and multi-year renewals.
For B2B founders navigating the messy reality of finding product-market fit and building repeatable go-to-market motions, Rising Team’s journey offers something more valuable than best practices: specific decisions, with specific reasoning, that produced specific outcomes. The kind of tactical insights you can actually apply to your own context.
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