In this edition of Ellen’s Three Things, in light of our recent funding announcement of $113 MM led by KKR and Bessemer Venture Partners, I want to share three milestones that signaled to me that we were building a generational technology company—one that doesn’t just succeed but reshapes an entire industry.
These moments aren’t just about the numbers or accomplishments, but the foundations: customer value, trust, and a shared vision with our customers and investors.
1. ROI metrics for the Payments module exceeded our expectations
Every founding team starts with hypotheses. We had done the work—countless customer interviews, co-development of our first product Payments, and ensuring our strategy and foundations were strong. But as every founder knows, there’s always uncertainty when running a startup, where most things don’t go as planned and pivots are the norm.
After deploying our first product Payments module to our initial customers in 2021, we crunched the numbers to assess the value we were delivering to our customers. The analysis came in, and they were even better than we’d hoped. I remember looking at each other during our leadership meeting and everyone having a moment of “Holy smokes, this actually works...better than we expected!”
This was also underscored in the wild. I attended an alliance conference where we were running a demo to an audience. Midway through, an Aiwyn customer, unsolicited, exclaimed, “This shit works!” This kind of visceral reaction—it’s something every founder dreams of.
💡 Lesson: Everything else falls into place when you deliver true, 10x value to your customers. Get that piece right to go very far.
2. Investor reaction was overwhelmingly positive
In 2023, the macroeconomic environment was bleak. Headlines were filled with stories of tough times in venture funding, and the trough of disillusionment was deep. But we knew what we had. We knew our business. We saw the numbers, the trajectory, and the strength of our strategy.
We thought, *we don’t know what’s going to happen—it could go either way because the macro environment is so hostile—but our business is strong.* So we went out to test the fundraising markets.
What happened next is something founders only dream of: we received 10+ term sheets within a month from both venture capital and private equity firms. That response from the capital markets was an incredible validation—not just of our conviction in the business but also of the market’s recognition of our potential.
All of our hard work culminated into this $113MM fundraise that we just announced, where we partnered with Bessemer Ventures, the GOAT of vertical SaaS venture investing and KKR, an unrivaled force in the realm of private equity and venture capital investing.
It was a moment that underscored how far we could go.
💡 Lesson: Build a great business and everyone, including customers, investors, and partners, will want to work with you.
3. When we announced PracticeOS at Unlock, our user conference
Earlier this year, we hosted our third user conference in Nashville, and it was a moment to celebrate. Each year, the conference has grown in size and energy, and this latest one was no exception. It was a joy to see so many passionate customers and leaders in our accounting profession come together.
At the conference, we unveiled pivotal product developments—most notably, PracticeOS. As a founding team, you always set your sights on a North Star. But the journey toward it is rarely linear. You don’t know exactly how long it will take, or whether the destination might shift along the way—and that’s okay.
When we announced the vision for PracticeOS, it wasn’t just a product milestone. It was the realization that we were building on the strong foundation we had created—our incredible customer love, our innovative technology, the trust we had built over years of consistently delivering—and we were accelerating toward the future we had dreamed of.
I knew then that we had hit an inflection point and we were on our way to delivering the kind of transformational technology that accountants not only need but deserve.
💡 Lesson: A vision is only as strong as the foundation supporting it. Building trust and delivering consistent value over time creates a flywheel that gives you the right to further expand and serve.
These milestones underscore what it takes to build a generational technology company. It’s not just about big wins—it’s about the steady, unrelenting focus on solving real problems, creating transformative value, and building trust with customers, investors, and your team.
These moments remind me of why we started Aiwyn: to empower the accounting profession with technology that drives impact and unlocks potential. The road ahead is exciting, and we’re more energized than ever to keep building, innovating, and delivering on this vision.
The best is yet to come.
