About Us and Why We’re Hiring

We’re YNAB (“why-nab”), a financial education company with a spendfulness app that helps people all over the world spend their money (guilt-free!) on what matters most. For over 20 years, YNAB’s proven method has been changing lives—and people can’t stop telling their friends about the difference it’s made. Think: debt paid off, marriages strengthened, goals achieved, stress erased, and sleep finally restored. But don’t just take our word for it—dive into our vibrant communities on Facebook, TikTok, and Reddit (really!) or skim through our glowing app reviews. You’ll quickly see why people rave about YNAB and why we’re so passionate about creating something that truly changes lives for the better.

Big things are happening at YNAB, and we’re strengthening our executive team to help guide what’s next. 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.

What We’re Looking For

Hard Requirements

For this role, you must: 

• Live in the United States and be authorized to work here
• 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

Preferred Qualifications

These aren’t required, but are likely to set you up for success: 

• Experience with B2C SaaS or subscription-based business models
• Experience at a small to mid-sized company
• MBA, CPA, or similar experience/certification

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. 

Life at YNAB

That’s a quick snapshot of what we’re looking for. Before we go further, let’s make sure you’re excited about working with us. We’ll share more about YNAB, then dive into the role details and application process (be sure to read all the way to the end!).
YNAB started in 2004 and we haven’t taken any outside funding—we’re established, profitable, and in this for the long haul. We have one overarching requirement when it comes to joining our team: our Core Value Manifesto has to really click with you. If you’re nodding emphatically while reading it, you’ll probably like it here!

We live our core values every day at YNAB, and we mean it when we say we are an equal opportunity employer. We believe a diversity of backgrounds, abilities, and experiences is critical to our success, and we are passionate about creating a welcoming and supportive environment for every employee. All are encouraged to apply as we continue growing a smart, hard-working, and diverse team that loves building something that matters.

We also work really hard, together, to make working at YNAB an amazing experience. We’re (humbly) proud to have received many of Fortune’s “Great Place to Work” awards over the years, including #1 two years in a row! We have a team of truly exceptional people—the kind you’ll be delighted to work with. Let’s introduce you to a few of them!

Who You’ll Work With

The Executive Team

You’ll be a close partner to Todd, our CEO. Todd started at YNAB in 2010 after a search for a spending management solution evolved into a conversation with YNAB’s founder, Jesse. One job led to another, and since then he's been a part of developing and scaling up Support, Product Design, and Product Management at YNAB until, in February 2021, he became the CEO. Being a CEO keeps him pretty busy, so he otherwise keeps it as simple as he can—eating, sleeping, sitting, feeding the birds, cutting flowers, and ultrarunning.

You'll also sit on the executive team with the co-founders, Jesse and Taylor, as well as Angela (Head of Support), Lindsey (Head of Marketing), Sebastian (Head of Technology), and Sarah (Executive Assistant). They’re a tight-knit group who are passionate about YNAB, and you’re going to love joining forces with them. 

The Operations Team

Lauren is our accounting lead. She’ll be one of your direct reports, and someone with whom you’ll work closely on all things accounting (naturally). She loves obsessing about numbers and the stories behind them. When Lauren’s not jamming on her 10-key, you can catch her attempting a new recipe or trying a new pizza restaurant with her family. 
Caitlin, Carolyn, and Charlene will also report to you. They are, respectively, the HR, legal, and people leads at YNAB. Collectively, they manage our nine-person operations team. Outside of YNAB, you’ll probably find Caitlin drinking Diet Coke and wrangling her three little boys, Carolyn eating dark chocolate and planning her next Disney vacation, and Charlene on a slow, 11-mile treadmill run (you can ask her why when you meet).

Honestly, your role will touch almost every corner of the company, which means you'll cross paths with just about everyone at some point. We can’t even list them all, really. But rest assured, the entire team is looking forward to connecting with you!

How You’ll Work at YNAB

Now that you’ve learned about some of your future teammates, let’s talk more about YNAB and what it’s like to work here.

Building a Good Company

At YNAB, we think one of the best things we can offer is the chance to do meaningful work alongside people you respect, admire, and genuinely enjoy. And we mean that—from the beginning, we’ve been intentional about creating the company we want to work for. 

Along the way, we’ve learned that great teams aren’t built on perks or fancy titles—they’re built by bringing together high performers who thrive on tough challenges and share a commitment to doing exceptional work. We value discipline and ownership over unnecessary layers of process, and look for people who wake up excited to get important things done.

That’s the team we’re building at YNAB: one that cares deeply, works pragmatically, and always finds time to laugh (mostly at ourselves).

Live Anywhere in the U.S.

We’ve always been a fully remote team, and have people all over the world. For this particular position, however, we’re only considering candidates based in the United States. Anywhere in the U.S. is fair game, just make sure you have a reliable internet connection. 

A Human-Sized Work Week

We want everyone to have a full life outside of YNAB, and we seldom work more than a standard work week. Occasionally things get busy and people put extra time in—but then we encourage them to take extra time off, too. We work hard and smart, but at a measured pace. Remember, we’re in this for the long haul. 

Flex Your Schedule

As a remote team, a lot of our work is done asynchronously—but we also love working together in real time. We try to schedule most meetings from 12-3 pm Eastern, Monday-Thursday. Outside of your meetings, we trust you to set your schedule by balancing your team’s needs with your own needs. You don’t need to ask for permission to take off early for an afternoon appointment, or be “active” on Slack if you’re working deeply on a project. We look at what you accomplish, not how long you're in front of a computer.

Take Vacation (Seriously)

We want you to take vacation—it’s good for you, and it’s good for YNAB. We don’t track your time off, and trust you to know when it’s time to step away for a vacation. Most YNAB team members take three or four weeks per year, plus two additional weeks for our company-wide December Break. It’s important to get plenty of downtime to get out and do something. We’ll look forward to seeing pictures in our #office-wall Slack channel! 

Meet the Team IRL

While we’re a fully remote team, you can expect to travel periodically throughout the year—not too often, but regularly enough. You’ll travel quarterly to meet with the executive team, and once or twice a year for other purposes. The latter might include attending Fan Fest, an Operations team meetup, or even in-person coworking sessions with Todd.

And we can’t forget to mention our biennial company retreat! At the YNAB retreat, we love to catch up on spreadsheets and powerpoints in a Best Western conference room. Just kidding. To give you an idea, we’ve been to Costa Rica, a gigantic cabin in the mountains, a ranch in Montana, Palm Springs, and most recently, Cape Cod. We work together, play together, and strengthen the bonds we’ve made as a team and company. At the end of each retreat, we feel energized, inspired, and excited to tackle the work ahead.

Up Your Game

We’re serious about helping you improve your craft, and will provide you with a professional development stipend each year. Think conferences, online courses, coaching, and dedicated time away from work to learn something new. We love to see our people grow!

Other Benefits

Our team is spread all over the world—mostly in the United States, but also in the UK, Canada, Germany, Brazil, Mexico, and several other countries. Everyone is eligible for our generous paid family leave, vacation, holidays, and sick time. 

Since you’re based in the United States, you’ll also be eligible for our health, dental, and vision insurance, where we cover 100% of the premium for you and your family. No need to check your vision, you read that right—100%. (Although if you did need to check your vision, NBD, we’ve got you covered!) 

We also have a Traditional and Roth 401(k) option, where YNAB matches your contributions up to six percent with immediate vesting. (Are you a personal finance junkie like our founder Jesse? He set up YNAB’s 401k to have the lowest fee structure possible, where all plan costs are paid by YNAB, not your retirement nest egg. The investment funds available are fantastic, passively-managed, ultra low-cost index funds. Not a PF junkie? Trust us, it’s awesome.) 

Competitive Compensation

At YNAB, we are dedicated to providing equitable, market-driven, and data-informed compensation, along with a competitive benefits package. The starting salary for this role will range from $175,000 to $250,000 USD annually (with the higher end reserved for the most experienced candidates). Additionally, you'll be eligible for an annual raise and profit-sharing twice a year. When YNAB succeeds, so do you—that’s the idea.

A Few Other Tidbits

• Once you start, we DEMAND (in a friendly, ALL CAPS IS YELLING way) that you fill out your “bucket list” spreadsheet with 50 items. (That’s harder than it sounds!) 
• We love to celebrate with you when you complete something on your bucket list—AND, we love using your bucket list as inspiration for your birthday present! 
• We want you firing on all cylinders, so we’ll set you up with a shiny new computer and replace it every three years.  
• Did we mention that YNAB makes a huge, positive difference in people’s lives? You may not think that matters, but then a few months down the road you’ll realize it’s made your job really, really enjoyable. Don’t underestimate this!

If this sounds like your ideal environment, read on because now we want to talk about you, and how you’ll play a big part in changing people’s lives.

Now back to you, our new Head of Operations....

Our mission is to teach everyone to love how they spend their money. No small thing, right? To get there, we need operations that are thoughtful, well-designed, and effective. That's where you come in. 

You’re our person if:

• You're an exceptional strategic finance leader who thrives across boundaries. You possess the extraordinary combination of operational finance expertise and revenue strategy in B2C SaaS, while effortlessly shifting between finance, HR, legal, people, and other domains—understanding the nuances of each world without getting lost in translation.
• You lead with confidence and humility. You can guide cross-functional teams without having to master every domain, honoring others' expertise while providing clear direction.
• You put people at the center. You understand that behind every policy and financial decision are real people—both team members and customers—and you work to ensure they all feel valued. 
• You simplify complexity. Whether tackling tax issues, legal considerations, or financial forecasting, you provide clear, decisive recommendations without getting lost in the details.
• You're both practical and forward-thinking. You manage tradeoffs effectively and have a sense for when to add process and when to remove friction to support growth.
• You don’t just support great work—you do great work. You don’t hesitate to jump into the details, from tax nitty-gritty to contract deep dives, and everything in between. 
• You align with our core values. Operations at YNAB isn't just about keeping things running—it's about building the company we want to work for, and protecting it at all costs. Really, this bullet comes first.

What you’ll do at YNAB:

Strategic & Operational Finance

• Partner with our CEO to build a financial strategy that balances immediate growth with long-term sustainability, using business model optimization to keep us financially healthy at every stage.
• Create clear financial metrics, reports, and forecasts that enable executives to make confident, data-driven decisions while working with our accounting lead to manage cash flow and tax planning.
• Collaborate with our Product and Marketing teams on subscription models, pricing structures, and retention levers, and with our executives on revenue planning and long-term financial sustainability.
• Work alongside our accounting lead to maintain strong, reliable finance operations—whether it’s sorting out spreadsheets, handling vendor docs, or staying on track with compliance filings.

People, HR, & Culture

• Balance compliance with flexibility by consistently making people-first operational decisions that respect both regulations and our culture.
• Partner with our HR lead to develop competitive compensation packages, meaningful benefits, and sensible employment policies that attract and retain great (really, really great) people.
• Create an environment where people can do their best work, feel valued for their contributions, and have clear opportunities to develop their skills and advance their careers.

Legal & Risk Management

• Provide thoughtful perspective on risk decisions across the company, helping teams make choices that protect our business without stifling innovation or growth.
• Work alongside our legal team to find the right balance between compliance requirements and business objectives, turning potential obstacles into workable solutions.
• Develop practical, pragmatic policies that give the team clear guidance without creating unnecessary red tape or bureaucracy.

Operations & Cross-Functional Leadership

• Champion a culture of continuous improvement, where we regularly revisit how we work to find and fix bugs in our company before they become larger problems.
• Make decisions that balance ideal theoretical approaches with practical realities, focusing on solutions that deliver tangible business results rather than just looking good on paper.

Whew—that’s a big list! To sum it all up, let's say your success as Head of Operations comes down to this: Your ability to create systems that enable every team member to focus on what they do best—all while ensuring YNAB remains financially healthy and true to its mission for decades to come. If this sounds like the kind of work that lights you up, let’s talk!

How to Apply

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.)

Tips

• 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. 
• If we can help with an accessibility need, email us at accommodations@ynab.com and indicate in the subject line that you’re applying for the Head of Operations role. (We can only respond to messages related to accommodations.)
• Finally, please click here for an outline of what this hiring process will look like. It’s rigorous, but truthfully, people say it’s fun!

We look forward to hearing from you!