Penny

I joined Penny when there were five of us. In those early days I was responsible for product, design, marketing, and a fair amount of whatever else needed doing. As we grew, I built and led a product team of around 10 people and remained part of the executive team, helping shape company strategy, fundraising, and the direction of the product.

The original idea was pretty simple: give independent salespeople an intelligent assistant that could help them figure out what to do next.

For people working in direct selling, that meant using customer data, purchase history, and machine learning to recommend who to contact, when to follow up, and what products to suggest. Rather than making people learn how to use a traditional CRM, we wanted the software to do more of the thinking.

The early traction was remarkable.

We went from a handful of users to 15,000 in three months without spending anything on marketing. People were finding the product, sharing it with their teams, and using it to run their businesses. That organic adoption eventually caught the attention of the enterprise companies those users worked with.

What started as a tool for individuals became a platform serving large international organizations.

Over the next few years, Penny reached hundreds of thousands of users across approximately 20 enterprise customers and around $5M in annual recurring revenue. We grew from five people to more than 130 and raised institutional funding, including a $27M Series B.

More importantly, we could demonstrate the product was working. Our 2021 investor materials reported $28.8M in incremental customer sales and $41.4M in recovered revenue attributed to the platform.

Of course, the story wasn't all up and to the right.

The traditional direct-selling industry was changing, and the growth of the creator economy was shifting how brands worked with independent sellers. Eventually, we made the difficult decision to substantially reduce the size of the company and move into a different market.

That became Endlss.

Penny taught me a lot about product-market fit, building teams, and turning bottom-up product adoption into enterprise revenue. It also reinforced something I've come back to repeatedly since: building a product people love is important, but understanding how the market around that product is changing matters just as much.