Rising Team’s Remote Fundraising Playbook: $11M Raised, One In-Person Meeting

Rising Team’s Remote Fundraising Playbook: $11M Raised, One In-Person Meeting

The highest valuation offer is rarely the best deal. Jennifer Dulski knows this from two perspectives: as a founder raising capital for Rising Team, and as a Stanford business school professor who teaches case studies of founders who chose wrong.

In a recent episode of Category Visionaries, Jennifer Dulski, CEO and Founder of Rising Team, shared how she raised the company’s funding entirely remotely—and why the investors who gave the highest numbers weren’t the ones she chose. This isn’t about leaving money on the table. It’s about understanding what actually matters when you’re signing up for a multi-year partnership.

The Stanford Classroom Advantage

Most founders learn about investor selection through trial and error. Jennifer had a different vantage point. She teaches classes at Stanford’s business school about scaling growing companies, where she regularly brings in founders to discuss their journeys and dissects case studies of other companies.

“I teach in class where I bring in guests and we do cases of other peoples businesses and there are so many examples of people kind of choosing the wrong investors,” Jennifer explains.

This isn’t academic theory. These are real companies, real founders, real consequences of optimizing for the wrong variables. When you see the pattern repeatedly—founders chasing valuation bumps, then spending years dealing with misaligned investors—the lesson crystallizes.

The principle sounds obvious: choose investors aligned with your mission and focused on the long term. But obvious doesn’t mean easy, especially when you’re staring at term sheets with different valuations and different amounts of capital.

The Core Insight

Here’s what Jennifer learned from studying those case studies and applying it to Rising Team’s fundraising:

“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.”

This runs counter to how most founders approach fundraising. The conventional playbook is to maximize valuation—it’s how you win the Twitter announcement, how you justify your trajectory to employees, how you measure progress against other companies in your space.

But valuation is a moment-in-time metric. Investor alignment is a multi-year reality. The extra points on valuation feel great for a week. The wrong investor makes every subsequent decision harder for years.

Jennifer chose differently: “So I feel like we’ve chosen our investors very thoughtfully and we have an incredible group of investors who feels really mission aligned, really focused on the long term, really supportive of the company.”

Notice the criteria: mission aligned, long-term focused, supportive. Not highest valuation, not most capital, not most prestigious brand. These are relationship qualities, not transaction metrics.

The Fully Remote Reality

What makes Rising Team’s fundraising story particularly relevant is how it happened. Jennifer raised the entire round on Zoom. In a fundraising process that traditionally involved dozens of in-person meetings, multiple office visits, and relationship building over meals, she met just one investor face-to-face before closing.

Some investors she still hasn’t met in person years later.

This wasn’t a pandemic adaptation that they’re eager to move past. It’s the new normal for how capital gets raised, especially for companies that understand what really matters in investor evaluation.

The question is: if you can’t rely on in-person chemistry and office visits, how do you actually evaluate alignment?

Evaluating Alignment Remotely

The challenge of remote fundraising isn’t pitch delivery—Zoom works fine for presentations. The challenge is evaluating fit. In person, you pick up signals from body language, energy, how they interact with their colleagues, what happens in informal moments.

Jennifer’s approach centered on understanding what investors actually cared about beyond the pitch. Mission alignment isn’t about investors saying the right things during diligence. It’s about what they’ve done with their other portfolio companies, how they’ve behaved during difficult moments, what they actually prioritize when companies face trade-offs.

These signals are discoverable remotely, but you have to be intentional about seeking them out. The thoughtful investor selection Jennifer describes required doing real work: talking to other founders in their portfolio, understanding their approach to supporting companies, getting clear on their expectations and timeline.

This is where teaching at Stanford created an advantage. Jennifer had seen the patterns of what good investors do versus what they say they do. She knew which questions to ask and which answers actually mattered.

The Long-Term Optimization

The case for prioritizing alignment over valuation becomes obvious once you think about the actual relationship. Investors aren’t just capital providers—they’re partners who will influence major decisions for years.

When you’re deciding whether to pursue enterprise deals that require longer sales cycles, your investors’ orientation matters. When you’re choosing between growth and profitability, their expectations shape the viable options. When you’re facing a down market and need to adjust strategy, their support or pressure determines what’s possible.

Mission alignment means your investors understand and support the actual vision you’re building toward. Long-term focus means they’re not pushing for exits or growth metrics that don’t serve the business. Supportiveness means they’re helpful when things get hard, not just when everything’s going well.

These qualities sound soft until you face actual strategic decisions. Then they become the difference between investors who help you build the company you want versus investors who push you toward outcomes that serve their fund dynamics.

The Valuation Trade-Off

This doesn’t mean valuation is irrelevant. Jennifer isn’t arguing for accepting any valuation as long as investors are nice. The point is more subtle: past a certain threshold of reasonable valuation, the incremental gains from optimization matter less than the qualitative differences in partnership.

If Investor A offers $5M at a $20M valuation and Investor B offers $5M at $25M, that’s a meaningful difference. But if Investor A is mission-aligned with long-term focus and Investor B is pushing for a quick exit, the valuation premium probably isn’t worth the partnership cost.

The extra $5M in valuation is immediately dilutive to founders and employees. The wrong investor creates friction in every board meeting and strategic decision for years. The math isn’t even close when you think beyond the moment of signing.

The Stanford Case Studies

Jennifer’s perspective isn’t just from her own fundraising. She regularly sees what happens when founders optimize wrong:

“I’ve seen this really well because I teach in class where I bring in guests and we do cases of other peoples businesses and there are so many examples of people kind of choosing the wrong investors.”

These case studies reveal patterns. Founders who chase valuation end up with investors who push for aggressive growth that doesn’t fit the market. Founders who pick prestigious funds end up with partners who are stretched too thin to be helpful. Founders who take the largest checks end up with investors whose ownership requirements create problems in subsequent rounds.

The consequences play out over years. Rising Team is still in the early chapters of its investor relationships, but Jennifer made choices informed by watching how these relationships evolve across dozens of other companies.

The Rising Team Investor Group

The result of this thoughtful selection process is an investor group that Jennifer describes as “really mission aligned, really focused on the long term, really supportive of the company.”

This alignment matters in concrete ways. When Rising Team makes strategic decisions—like their pivot from one-on-one to team sessions, or their choice to pursue enterprise customers through structured pilots rather than quick deals—their investors support these choices because they understand the long-term vision.

When they face the inevitable challenges that every startup encounters, they have partners who are genuinely helpful rather than just demanding status updates. When they need to make trade-offs between metrics, their investors understand which outcomes actually matter for the business they’re building.

These aren’t just nice-to-have qualities. They’re the difference between investors who compound your advantages versus investors who add friction to every decision.

The Principle for Other Founders

The lesson for founders raising capital is clear but hard to follow: optimize for the multi-year partnership, not the moment of signing.

This requires discipline when you’re looking at term sheets. The highest valuation creates psychological pull. The largest fund has brand appeal. The fastest close feels like momentum. But none of these correlate with what actually matters: alignment, long-term orientation, and genuine support.

Jennifer’s advantage was seeing this pattern through her teaching. Most founders have to learn it through experience. But the pattern is discoverable if you do the work: talk to other founders in investors’ portfolios, understand how they’ve behaved through difficult periods, get clear on what they actually prioritize beyond the pitch meeting pleasantries.

And in a world where fundraising happens on Zoom, these signals are just as discoverable remotely as they were in person. You just have to be intentional about looking for them.

For Rising Team, this approach created an investor group that enables the company to focus on building the team performance platform that serves Fortune 500 companies, school teachers, and government agencies alike. That long-term vision requires long-term investors. Jennifer chose accordingly.