Head of Operations, YNAB

• Have at least five years of total experience in operations, ideally at the director level or higher
• Have at least three years of financial operations leadership experience (think strategic finance, revenue optimization, partnerships, and monetization)
• Have experience scaling operations at a dynamic, growing company with cross-functional concerns (managing teams across finance, HR, legal, and/or people operations)
• Be willing to travel about five times per year, typically for one week at a time
• Note: If you believe you’re a fit for this role, but don’t meet our preferred qualifications, we still encourage you to apply. While our hard requirements are non-negotiable, we’re otherwise open-minded, and don’t need you to be the perfect candidate on paper

Desirable

• We’re looking for a strategic, hands-on leader to join our executive team and own our operations function, including finance, HR, people, and legal, so these are seamlessly supporting the company’s growth
• This role blends high-level strategy with deep operational execution, acting as a connector between the financial health of the business and the underlying systems that drive it
• As Head of Operations, you’ll sit at the intersection of financial strategy, operational excellence, and company culture
• You’ll make decisions that strike the right balance between pragmatism, compliance, and long-term vision
• We’re looking for someone with a finance-first background who’s also passionate about building thoughtful, people-centered operations
• And we really can’t stress this enough: YNAB’s impact starts with its people
• This role plays a key part in ensuring YNAB remains a place where great people love to do their best work

• Please be yourself! ChatGPT can sit this one out
• If you meet our hard requirements and follow the application instructions, we promise a real human will review your materials
• You’ll only be able to apply once, so make sure your answers are final before you click submit. (You can start your application and come back to it later.)
• Keep an eye out for an email from @pinpoint.email titled Thank you for applying to YNAB! This confirms your application has been received. If you don’t receive it, please apply again
• Apply here by Sunday, July 13, 2025 at 11:59pm PT
• Heads up! We'll be reviewing applications as they come in rather than waiting until the deadline. While July 13 is our official cutoff date, there's a chance we might fill the position sooner if we find the right fit!
• What to include in your application:
• A resume
• Want to make sure we don't miss anything important? If possible, please highlight or point out on your resume where your experience aligns with our hard requirements and preferred qualifications (listed above)
• A cover letter, including:
• On page 1: Please introduce yourself and explain why you’re a great fit. This isn’t your typical cover letter—skip the fluff and formalities, and just help us get to know you
• Starting on page 2: Please answer each of these questions in 2-3 paragraphs or less
• 1. What excites you most about this role, and why?
• 2. If you had to pick the top qualities that separate good executives from great ones, what would they be, and why
• 3. Imagine you’re our Head of Operations. You’ve just come back from the annual executive meetup, where budget and hiring decisions for 2026 were finalized
• Before the meetup, Avery—a respected senior leader—made a compelling case for hiring a project manager to support her team
• The executive team rigorously discussed her proposal, but ultimately couldn’t approve the hire
• Now it’s your job to share the decision with Avery
• What would you say to her
• Craft your response as if you’re writing to her directly. (Feel free to make assumptions about this scenario to guide your response.)