01
Stewardship
Create the trusted financial foundation beneath the company: accurate reporting, effective controls, an efficient close, finance operations and systems that leadership can rely on.
Will MastersonStrategic Finance Advisor
The most expensive problem in a startup never appears in the budget.
Everyone is working hard. They are not always working toward the same definition of success.
Strategic finance advisor to founders and CEOs.
The reality
Everyone can be right. The company can still be wrong.
As companies grow, each team develops its own view of what matters. Sales wants capacity. Product wants engineers. Operations wants infrastructure. Each decision may make sense on its own while pulling the company in a different direction.
I know because I have sat in the middle of those decisions. As CFO of AllTrails, I drove the financial and operating work behind more than 10× revenue growth. Most recently, I helped bring together the acquired businesses behind Visa Acceptance Solutions, a $2.5 billion global platform growing in the low 20s.
Earlier in my career, I advised technology companies on M&A at Greenhill and worked in CFO advisory at Deloitte. I have seen finance from multiple angles, sat in front of boards and translated strategic vision into financial commitments, operating plans and measurable results.
At every stage, the challenge is the same: more people, capital and opportunity create more versions of what matters.
Finance is what brings them together.
The philosophy
Most companies use finance to report the business. Few use it to run the business.
Finance should translate strategy into a shared operating plan, connecting people and capital to the company’s priorities. From the boardroom to the most junior person on the product team, everyone should understand what success looks like and the part they play in achieving it.
I help founders build that finance function through four roles: stewardship, resource allocation, accountability and scenario planning.
My operating lens
My framework for the role of finance
Over the course of my career, I have developed a four-part framework for the role finance should play in a growing company. Together, these capabilities connect reliable information with the decisions, resources and accountability required to move the company forward.
02
Resource allocation
Connect strategy to capital and people. Determine where the next dollar and next hire should go, what the company is buying with its runway and which opportunities justify further investment.
03
Accountability
Turn strategic priorities into explicit commitments. Establish the owner, resources, expected outcome, timing and evidence for each major initiative so the organization understands what success means.
04
Scenario planning
Translate uncertainty into financial choices. Understand what happens when assumptions prove right, wrong or take longer than expected, while preserving the company’s ability to respond.
The filter
Working together starts with a conversation.
I work with only a few founders and leadership teams at a time. It is the only way I can do work that materially improves the decisions in front of each company. A short note helps me understand what you are working through and whether I am genuinely the right person to help. No polish required. Just tell me where the company is stuck.
Start a ConversationFrom the other side of the table
The same questions shape how I invest.
I also invest in overlooked public companies where valuation, governance and capital allocation create a meaningful gap between price and long-term potential.
Whether working inside a company or investing from the outside, I return to the same questions: Where should capital go? What return should it produce? Who owns the outcome? What evidence should change the decision?