Head of Finance

We’re looking for a Head of Finance to lead and own Leland’s financial and M&A strategy. As Leland’s first finance hire, you’ll be the architect of our financial systems, ensuring we invest in the right opportunities and scale efficiently. If you are excited about owning finance at a fast-scaling startup and passionate about driving impact while helping people achieve their career and educational dreams, we’d love to chat.

What you’ll be doing:

• Develop and execute a comprehensive financial strategy to support Leland’s growth, ensuring we can scale efficiently

• Design and implement robust financial systems, processes, and controls to ensure organizational efficiency, transparency, and scalability.

• Maintain accurate financial forecasts, monthly reports, and performance metrics, partnering with cross-functional teams to track key business indicators and identify growth opportunities.

• Provide financial insights to support growth initiatives, collaborating closely with marketing, operations, and other teams to make data-driven decisions.

• Work closely with the CEO on strategic projects like M&A, investor relations, board communications, and future fundraising efforts.

• Work with accounting/tax teams to ensure we are accurately reporting and in compliance.

• Oversee the development of budgeting, pricing, and financial planning strategies, ensuring they align with Leland’s goals and objectives.

• Lead the structuring and diligence process for any M&A that Leland elects to pursue, including securing funding and ensuring the deal is executed smoothly.

Your skills & experience:

• 8-10+ years of experience in finance, investment banking, private equity, or related analytical roles, ideally in a startup or fast-paced environment.

• Strong quantitative and analytical skills, with proficiency in Excel and financial modeling.

• Proven ability to lead strategic finance initiatives and build a finance organization from the ground up.

• Experience working closely with senior leadership and contributing to high-level strategy and decision-making.

• Hands-on and scrappy mindset—you’re not afraid to dive into the details while driving high-level strategy and growth.

• Excellent communication and collaboration skills, with the ability to work cross-functionally and influence key stakeholders.

Why Leland?

• Opportunity to own finance at a high-growth startup with a deeply impactful mission.

• A collaborative, high-energy environment where your contributions will have a direct impact on the company’s growth.

• Competitive salary and benefits.

• The chance to join a passionate team helping people achieve their career and educational goals.