About Woodrow

Enterprise finance and operations teams run critical processes across multiple systems. When traditional software can’t handle the work, people carry the load —and there’s no room for error.

Woodrow exists to make repetitive work scalable. We’re building an AI agent with finance and accounting expertise that follows defined guidelines, works across your tools, and documents every step, so you stay in control.

Like a stellar employee, Woodrow follows your instructions, learns from feedback, and works 24/7, so you can scale your team's impact without ramping up headcount.

We’re builders and operators focused on one thing: making AI agents accurate and reliable in enterprise finance and operations.

Leadership

Sidharth Kakkar

Founder

Sidharth is a repeat founder who co-founded Subscript, a B2B SaaS finance platform, and previously founded and led Freckle (Front Row Education) through scale and acquisition.

At Woodrow, he leads product and technical direction, focused on building agents that execute enterprise finance and operations workflows with clear controls, predictable behavior, and audit-ready transparency.

He holds a B.S. in Computer Science from Carnegie Mellon University and an MBA from Northwestern University’s Kellogg School of Management.

Phil Sharp

Interim CEO and CMO

Phil has spent his career building growth engines for SaaS companies, with leadership roles at Udemy, UserTesting, and Brightwheel. He has partnered with Sidharth for years—as VP of Marketing at Freckle and later as CMO and Interim CEO at Subscript.

At Woodrow, Phil leads go-to-market, working closely with enterprise finance and operations leaders to turn real workflow pain into what the team ships.

He holds a B.A. in Molecular and Cell Biology and Education from the University of California, Berkeley.

Michelle Lee

Head of People and Operations

For more than a decade, Michelle has worked at the intersection of strategy and operations,  with experience spanning Bain & Company, Freckle, Greenlight, and Subscript, where she was Co-founder and Head of People and Operations.

Today at Woodrow, Michelle is focused on the team, culture, and internal systems that keep standards high as the business scales.

She earned her B.A. from Dartmouth College and an MBA from Harvard Business School.

Investors

The Woodrow Standard

A manifesto for reliable and accurate AI

We’ve spoken with hundreds of finance and operations leaders. The excitement around AI is real, but so are the concerns: how do you scale without sacrificing accuracy; how do you maintain visibility across systems; and how do you make sure you’re not introducing a black box into processes that already have enough complexity.

Woodrow is built around a simple belief: enterprise finance and operations teams should be able to delegate repetitive work to AI with confidence. Here is how the team builds toward that standard.

Control is non-negotiable

Our job is to help enterprise finance and operations teams automate more work while making the process easier to trust, review, and defend. If Woodrow changes a record, sends a message, or reconciles a number, the customer should be able to see exactly what happened and why, with full transparency and the precision to stand up to audit.

AI built for the real world

Our customers rely on us for automation that holds up under real conditions—even as edge cases arise, policies evolve, and tools change. We build for repeatability so the same inputs produce the same outputs, and customers can run their processes with confidence in the accuracy of each result.

Act with urgency and rigor

We operate with urgency because customers feel the cost of manual work every day. Our default is to make progress in controlled increments: clear owner, clear scope, and clear success criteria. We pair that speed with rigor, grounding our work in finance and accounting principles and holding a high bar for correctness.

We’re committed to developing an AI agent that is powerful without being flashy, capable without pretending to be boundless, and honest about what it can and can’t do.

‍Woodrow is built to a finance-grade standard, measured by accuracy and operability, not novelty.

About Woodrow

We’re builders and operators focused on one thing: making AI agents accurate and reliable in enterprise finance and operations.

Amplify your team’s impact with powerful and accurate AI.