Founders Everywhere: Jacob Allen
Jacob Allen is the co-founder and CEO of Reportwell, an AI platform that streamlines compliance and reporting for government agencies, authorizers, schools, and school districts.
Welcome to Founders Everywhere, where we highlight the incredible people behind the companies we’ve backed at Everywhere Ventures, a global pre-seed fund supported by a community of 500 founders and operators.
Regulatory compliance is one of the most overlooked burdens for institutions. For years, organizations have relied on spreadsheets, emails, and outdated systems to manage compliance and governance. Reportwell replaces that patchwork with a single AI-powered platform for streamlined reporting and regulatory compliance for governmental agencies, charter entities, and school districts. The company is currently serving customers across 17 states and is fielding inbound interest from banks, law firms, construction companies, and federal agencies. By making compliance faster, more accurate, and easier to manage, Reportwell frees teams to focus less on paperwork and more on delivering impact.
Co-founders Jacob Allen (CEO), Lani Luo (COO), and Jennica Adkins (CCO) met over 15 years ago as Teach For America teachers in Chicago, where they lived together before relocating as a group to open charter schools in Indianapolis. Co-founders Jacob Peters (CPO) and David Spitz (CFO) later joined to grow the footprint of the school network. As school leaders, they became frustrated with the clunky, error-prone compliance processes that were used to deliver reports to city, state, and federal agencies. Determined to solve the problem, they moved to Detroit to build Reportwell, inspired by the robust funding and engineering ecosystem. According to Jacob, CEO, the team still travels, works, debates, and celebrates together like family, a dynamic they credit with helping Reportwell maintain 100% customer retention over the past three years. Jacob has also been named to the Forbes 30 Under 30 list, received the King of Color award from Morehouse College, and was inducted into the University of Washington Hall of Fame. He shares more about Reportwell and why modernizing compliance has become a much bigger opportunity than anyone expected.
What’s Reportwell’s North Star?
Our North Star is regulatory compliance and governance: making the messy, manual, risk‑filled processes around laws, policies, and oversight much more reliable and intelligent. We want boards, superintendents, and industry leaders to have a clear, AI‑assisted view of what they’re responsible for and how they’re performing against those obligations, instead of relying on scattered spreadsheets, emails, and human memory.
What sets Reportwell apart?
We built Reportwell around how organizations actually manage compliance, not how software assumes they do. Before us, teams relied on custom-built internal systems, disconnected software, or manual processes using documents, email, and spreadsheets. By working closely with customers and mapping decades-old workflows, we created a platform that mirrors real-world operations while using AI to simplify and modernize compliance without forcing organizations to reinvent how they work.
Tell us about some recent milestones that Reportwell crushed.
There are three that stand out:
We’re ahead of our revenue projections this year.
We’re getting serious inbound from industries we thought we’d tackle years down the line; for example, the largest hospital system in the Midwest called us and said they wanted Reportwell now, and we’re in the process of rolling out to about 35 hospitals.
We haven’t lost a customer in three and a half years, zero churn. Many of our customers are signing three‑ and five‑year deals and say they love both our product and our team, which is exactly the kind of relationship we were hoping to build.
How has Reportwell evolved over time?
We started in K–12, helping school boards and districts manage compliance, governance, and documentation. As we built deeper AI and workflow capabilities, other industries began knocking on our door: healthcare systems, law firms, banks, restaurants, construction companies, and even a national federal agency we can’t name yet. They all said essentially the same thing: “We have the exact same antiquated, manual problems.” What’s been surprising is how often the software just works out‑of‑the‑box for these adjacent use cases. Regulation is much bigger than education, and we’re excited to tackle large, sticky compliance problems far beyond K–12.
How has your background influenced your approach to building Reportwell?
I started in the classroom more than 15 years ago as a Teach For America teacher in Chicago, where I met my co-founders. Early on we thought the big problems in public education were mostly inside the classroom: curriculum, instructional days, teacher preparation. Later, when we opened our first charter school, we saw a different layer of problems: operations, finance, governance, legal, and regulatory compliance. Those ugly, behind‑the‑scenes issues were keeping K–12 stuck in an antiquated state. That’s why, when we decided to build something, we chose not to create another curriculum or tutoring program. Instead, we went after the hard stuff: operations, finance, governance, and regulatory compliance.
Before education, I also worked as a bartender and server, experiences that taught me the importance of listening to customers and delivering great service, values that still shape how we build our company today.
Fun fact:
My husband and I brew our own beer and make our own wine. Every Christmas, we break out our homemade beer to share amongst family and friends. One day we hope to own a hobby vineyard and farm to keep ourselves “rooted” to the land.
From the archives: Listen to Oban MacTavish with Jenny Fielding, on the Venture Everywhere podcast: In the Club with Spade. Now on Apple & Spotify. Check out all our past episodes here!
