The Rising Team Pivot: From One-on-One to Team Sessions in Six Months

The Rising Team Pivot: From One-on-One to Team Sessions in Six Months

The first version of Rising Team made perfect logical sense. Managers would use assessments and tools one-on-one with each person on their team. Personalized attention. Individual development. Deep dives into what makes each team member tick. The kind of thorough, thoughtful approach that leadership books recommend.

It was also completely wrong.

In a recent episode of Category Visionaries, Jennifer Dulski, CEO and Founder of Rising Team, shared how a fundamental misunderstanding about what teams actually need nearly derailed the company. The pivot that saved them wasn’t about building better features or finding new markets. It was about recognizing a human truth hiding in plain sight.

The Logical Product That Nobody Used

When Jennifer started building Rising Team in early 2020, she drew from decades of experience leading teams at Yahoo, Facebook, and Change.org. She knew what managers needed: better tools to understand and develop their people. The solution seemed obvious.

“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 it had the same kind of set of assessments and tools that you could use, but it was meant to be done individually.”

The logic was airtight. Managers constantly struggle to really understand their team members. How do they prefer to communicate? What motivates them? Where do they need development? One-on-one sessions provide dedicated time to explore these questions without the noise of group dynamics.

This is the kind of product that wins awards from HR thought leaders. It’s backed by research on individual development. It aligns with best practices about personalized management. On paper, it solves a real problem managers face every day.

But something wasn’t working. The product existed. Managers could access it. But the growth trajectory wasn’t there. Rising Team was solving a problem that managers agreed they had, using an approach that made complete sense, and still something felt off.

The Two-Part Insight

The breakthrough came from watching how the product was actually being used—and more importantly, noticing the gap between intended use and actual behavior.

“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,” Jennifer recalls.

The first reason was purely practical. Time efficiency.

“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.”

Do the math on a manager with eight direct reports. Eight separate sessions to go through assessments and tools. Even at 30 minutes each, that’s four hours of manager time, plus eight 30-minute blocks from team members. And that’s just for the initial assessment. Ongoing development requires repeated sessions.

The time commitment alone created a barrier. Not because managers didn’t value understanding their teams—they did. But because four hours of back-to-back individual sessions competes with everything else on a manager’s calendar. The product was asking for more time than most managers could realistically commit.

But time efficiency alone doesn’t transform a product trajectory. Plenty of tools save time without becoming essential. The second insight was what changed everything.

Teams Crave Connection

Here’s what Rising Team discovered: effectiveness wasn’t just about managers understanding their team members. It was about team members understanding each other.

“The other is teams really crave this. They really want to know each other better. They want to feel more connected. And especially in hybrid and distributed work, they feel that strongly,” Jennifer notes.

This is the insight that traditional management thinking misses. We treat team building as something managers need to do for their teams. A tool to improve performance. A mechanism to reduce friction. An intervention to solve problems.

But teams don’t just benefit from connection. They actively want it. They’re hungry for it. Especially in hybrid and distributed environments where casual interactions don’t happen naturally, teams are craving structured opportunities to understand how their colleagues think, work, and communicate.

The one-on-one approach solved the manager’s problem. The team approach solved something deeper: the human need to feel connected to the people you work with every day. This wasn’t just a feature change. It was a fundamental shift in understanding the job to be done.

The Sales Motion Transform

When you change what problem you’re solving, you change who buys and why. The one-on-one version of Rising Team sold to managers focused on individual development. The team version sells to leaders feeling acute pain about team disconnection.

The buyer persona shifted. Instead of targeting managers looking to improve their one-on-one skills, Rising Team now targets functional leaders whose teams are struggling with engagement, connection, or performance in hybrid environments.

“We tend to sell to functional and divisional leaders at large companies who have these pain points,” Jennifer explains. “Sometimes it’ll be a CMO or a CIO or a VP of engineering who says, I really want something like this for my team.”

These buyers aren’t shopping for management training. They’re solving urgent problems. Their pulse scores came back bad. Their distributed team feels disconnected. People are leaving because they don’t feel part of something. These are the pain points that get budget approved and decisions made quickly.

The value proposition changed too. Instead of selling time-efficient individual development, Rising Team sells team building that delivers measurable results. The platform helps leaders run interactive workshops that build connection and skills simultaneously, then channels those insights into an AI coach that provides personalized advice.

The Unexpected Benefits

The pivot from individual to team sessions unlocked benefits Rising Team didn’t initially anticipate. One was scalability. With the one-on-one model, a manager with eight people needed eight sessions. With the team model, one session serves everyone. The unit economics improved dramatically.

Another was data richness. When teams go through assessments and activities together, the platform captures not just individual preferences but team dynamics. How do different communication styles interact? Where are potential conflict points? Which combinations of people naturally collaborate well? This data feeds the AI coach and makes it exponentially more useful.

But perhaps the most significant benefit was creating a product that users actively wanted rather than something they knew they should use. There’s a massive difference between “I should do more one-on-ones with my team” and “My team is begging for more connection opportunities.”

One is guilt-driven adoption. The other is demand-driven adoption. Guess which one creates sustainable growth.

The Timing Factor

It’s worth noting when this pivot happened. Jennifer incorporated Rising Team in April 2020. The pandemic was forcing every team to confront distributed work challenges. The thing she thought was important suddenly became urgent for everyone.

“I built this because it was the tool I wish I had as a leader of teams throughout my career. I always wanted something like this, and it never existed. And then the thing that I thought was important overnight became urgent to everybody because building more connected, engaged teams, you know, when everyone’s team was remote, all of a sudden everyone really needed a way to help them do that.”

But timing alone doesn’t explain the pivot’s success. Plenty of team building tools existed when the pandemic hit. Most focused on fun activities or surface-level icebreakers. Rising Team’s insight went deeper: teams don’t just need activities, they need structured opportunities to understand each other in ways that directly improve how they work together.

The assessments and tools that made sense for one-on-ones made even more sense when the whole team experienced them together. Instead of a manager understanding each person individually, the entire team builds shared language and understanding simultaneously.

The Underlying Principle

The lesson here transcends team building software. It’s about the difference between solving the problem you see and solving the problem your users feel.

Jennifer saw managers struggling to understand their team members. True problem. Real pain point. Logical solution: give managers better tools for one-on-ones.

But the deeper problem—the one users felt acutely—was teams craving connection with each other. Managers weren’t just seeking to understand their people better. They were trying to create cohesive teams in environments where natural connection was becoming impossible.

The pivot succeeded because it solved the felt problem, not just the logical one. And in doing so, it transformed every aspect of the business. The buyer changed from managers to leaders. The pain point changed from individual development to team performance. The value proposition changed from time efficiency to measurable engagement improvements.

Most importantly, the adoption model changed from should-use to want-to-use. And that difference is what separates nice-to-have tools from essential platforms.

For founders building products that logically solve real problems but aren’t gaining traction, the question isn’t whether your solution works. It’s whether you’re solving the problem users feel most acutely. Sometimes those are the same thing. Often they’re not.