Head of Finance

Lassie; San Francisco (CA); On-site; USD 100,000 - 150,000; Full time

Job summary

Lassie, located in San Francisco, is searching for its first finance hire to establish robust financial operations from the ground up. In this pivotal role, you will work closely with CEO Steijn Pelle and advisor Jason Warnick, overseeing critical financial decisions and developing AI-native systems to enhance operational efficiency.

The ideal candidate has hands-on experience in a startup environment and is prepared to translate complex financial metrics into actionable insights for leadership. This unique opportunity will allow you to shape the company's financial future.

Qualifications

• Experience building financial operating models and scenario planning in a startup.
• Proven track record of managing finance operations hands-on.
• Ability to present complex financial data clearly to non-finance audiences.
• Experience implementing financial systems and processes from scratch.
• Familiarity with AI-driven finance solutions.

Responsibilities

• Establish and report on key financial metrics.
• Build and maintain the financial operating model.
• Ensure timely monthly closings and actionable financial statements.
• Manage the full FP&A cycle: budget, actuals, reporting.
• Partner with the CEO through future fundraising efforts.
• Develop AI-native finance infrastructure across various functions.
• Lead strategic finance projects beyond core FP&A.

Skills

Building operating models

Hands-on finance operations

Translating financial data

Implementing finance systems

AI-native workflows

Job description

Our mission is to help small businesses run themselves. We’re starting with doctors’ offices, building autonomous systems that handle busywork and complete the workflows that keep the office moving every day. Our team is small, flat, and ambitious. We value craft, intellectual rigor, and direct communication.

About the role

As Lassie's first finance hire, you'll build out the company's financial operations from the ground up. You'll work alongside CEO Steijn Pelle and Lassie advisor Jason Warnick (former CFO, Robinhood). You'll own the transition from founder-led finance to a world-class, AI-native function. This is a unique opportunity to build the systems that shape how Lassie grows and operates.

This role is as strategic as it is operational. You'll be involved in every major financial decision, from daily tradeoffs to strategic finance projects, and you'll be the person who gives the leadership team confidence in where the company stands and where it's headed financially.

What you'll do

• Establish and own the reporting of the company's key metrics (think active practices, ACV, ARR, net dollar retention, churn, payback period) so you can measure progress
• Build and maintain the company's financial operating model, including scenario planning and tradeoff visibility, so leadership can make confident resource and growth decisions
• Ensure an accurate, timely monthly close and deliver financial statements that give leadership an actionable view of the business
• Own the full FP&A cycle: budget, quarterly actuals, monthly reporting
• Serve as the CEO's key finance partner through future fundraises
• Build scalable, AI-native finance infrastructure across accounting, forecasting, spend management, and payroll, choosing tools that reduce complexity and grow with the company without overbuilding
• Lead strategic finance work beyond the core: pricing structure, sales commission design, rev ops foundations, and more

What we're looking for

Must-have

• You've built operating models, scenario plans, and unit economics from scratch in a startup environment, and you can defend your assumptions with board-level rigor
• You're a hands-on operator: you've closed the books, managed vendors, and run payroll, not just managed people who do those things
• You translate complex financial data into clear insights for a non-finance audience and are comfortable presenting to founders, board members, and investors
• You have a track record of implementing finance systems and building processes from scratch. You know when the current tool is right-sized and when it's time to graduate, and you don't over-engineer
• You've designed or built AI-native workflows for finance tasks, or have a strong instinct for where AI eliminates manual work without adding fragility

Nice to have

• You've owned a fundraising process or been the key finance partner in one. You know how to organize a data room, work through diligence questions, and build investor confidence through metrics and narrative
• You've managed a transition from outsourced to in-house accounting
• You've worked on rev ops, pricing strategy, or sales commission structures alongside core FP&A work

Joining us

To start, you'll have a handful of conversations with our team and founders. If there is mutual excitement, we'll invite you to the office where you'll work on a small project and meet the team.