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We're Hiring a Humbly Confident National Sales Director

We build “You Need a Budget,” the best budgeting software and educational resources around. (Those in the know call us YNAB, which is pronounced “why-nab”). For more than a decade, people have been using YNAB and then telling their friends what a difference it has made in their lives. Google us, or read some of our reviews on the app store, and you’ll see what we mean. We love building something that has a huge positive impact on people’s lives.

We are looking for an experienced sales professional to help grow our Financial Wellness Program. We want someone who is earnest about B2B sales, and understands the importance of a customer-centric process.

In this role, you’ll be laser-focused on helping us connect with HR benefits managers, PEOs, and businesses looking to boost their benefits package by empowering employees to take total control of their money with YNAB. This position will play a huge part in helping us build a long-term sales strategy that is authentically YNAB. (If you’re not familiar with us, keep reading—you’ll catch our vibe.)

You’re our ideal candidate if you love to connect with people, solve problems, and are known for being genuinely invested in helping others. You’re a critical thinker with an open mind, have top-notch communication skills, thrive in collaborative and autonomous environments alike, and always lead with empathy. You love to dream, and get that our dream is to help everyone eliminate financial stress through the life-changing power of a budget. 

Qualifications and Requirements*

  • You’re located somewhere in the 48 contiguous United States, and are able to travel within this region as needed. This one is a must.  
  • You have a minimum of 5 years of successful experience as a B2B sales representative obtaining new business. 
  • Experience in HR, PEO, and/or employer benefits sales models is preferred but not required.
  • You have experience selling to managers, directors, and VP levels within organizations.
  • You have a proven track record of consistently meeting or exceeding assigned annual/quarterly goals.
  • You’ve demonstrated consistent and persistent sales prospecting to identify new revenue opportunities and progress them through the entire sales cycle.
  • You’re attentive to forecasting and business reporting responsibilities. 
  • You recognize and deliver solutions for spoken needs as well as hidden or unspoken needs of suspects, referral partners, clients, and prospects. 

*If you know you’re a great fit for this role, but fall a little short on some bullet points, we encourage you to go ahead and apply. We don’t need you to be the perfect candidate on paper. On a similar note, we know impostor syndrome can be a powerful force, and may discourage fantastic people from applying. Please apply anyway. Many of us here have it too, so you’re in good company.

We promise to go into more detail about what you’ll be working on, but first, you need to know if you’ll even like working with us. Let’s talk a bit about life at YNAB.

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, and we can’t wait to connect with you!

We live our Core Values every day at YNAB, and we mean it when we say we are an equal opportunity employer. We believe that a diversity of backgrounds, abilities, beliefs, and experiences is critical to our success, and we are passionate about creating a welcoming, supportive, and collaborative environment for all employees. All are encouraged to apply as we continue to grow a smart, hard-working, and diverse team that loves working together to build something that matters.

We also work really hard, together, to make working at YNAB an amazing experience, and we were (humbly) proud to be named Fortune’s #1 Best Small Company to Work For two years in a row. We have a team full of truly exceptional people—the kind you’ll be excited to work with.  

Who you’d be working with:

You’ll be our very first sales hire, but don’t worry, you won’t be working in isolation. Here are a few of the people you’ll get to work with closely:

Chance, Head of Operations: Chance is who you’ll report to. He gets to obsess about building a great company and making sure that people really love their work at YNAB. He cares deeply about YNAB and the people who make it a success and has big plans for Financial Wellness by YNAB. He also oversees the company budget and financials. When he’s not championing the YNAB team experience, you’ll find him with his family outside in Southern Utah, usually on a mountain bike, a tennis court, or at the lake. 

Haley, PR Manager: Haley was our first PR hire and she has done ALL the things and worn all the hats for a whirlwind two years. True story: on Haley’s first day, we were in the middle of launching our YNAB for Good program and she jumped right in and made key improvements to the messaging like she’d already been on the team for 10+ years. She is full of strategic, big ideas without ever losing sight of the details. Not to mention punny, just so, so punny. 

Kody, Group Programs Manager: Kody is on a mission to bring YNAB to the masses through our Financial Wellness program, and has big dreams to introduce YNAB to college campuses nationwide. He also might just be one of the most helpful people you’ll encounter at YNAB (and that’s saying a lot, because everyone here is very helpful). Somehow, he has the inside scoop and answer to every single question you might possibly have. Maybe that’s why you’ll see him pop-up from time-to-time as the Question Master in our ever-popular #QuestionOfTheDay Slack channel. Blink twice and you might miss the monthly poster change in the background of Kody’s Zoom. From Star Wars to comic books, you never know what will pop up next month, but you can always count on Kody to champion your ideas and help make them possible.

You’ll also cross paths with—well—probably everyone else. People like Lindsey (our Head of Marketing), Arturo and Dane (a couple of our developers), Jen and Renae (two veteran support specialists), and Emily (a product marketing writer).

How You’ll Work at YNAB

Now that you’ve met some of your potential future teammates, let’s talk more about YNAB as a company. Here’s how we operate:

Live (Almost) Anywhere You Want 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 located in the 48 contiguous United States. Anywhere in that region is fine,  just make sure you have a reliable internet connection.

No Outrageous Hours

We want everyone to have a full life outside of YNAB, and we seldom work more than a standard work week. There have been a few occasions where things got busy and people had to put some extra time in. But then they took some extra time off, so it all balances out. We work hard and smart but we’re in this for the long haul.

Take Vacation (Seriously)

We want you to take vacation. In fact, we have a minimum vacation policy of three weeks per year. Five weeks feels about right (plus two extra weeks for our company-wide December break). It’s important to get plenty of downtime and get out and do something. We’ll look forward to seeing pictures of your adventures in our #office_wall Slack channel!

The YNAB Retreat

When the pandemic isn’t keeping us from traveling, we get the teams together once a year to catch up on spreadsheets and powerpoints in a Best Western conference room. Just kidding. So far, we’ve done Costa Rica, a gigantic cabin in the mountains, a beach house in the Outer Banks, a ranch in Montana, Laguna Beach, and most recently Palm Springs. We do really fun things at these retreats, but the highlight is inevitably just being together and having a blast.

Up Your Game

We’re serious about helping you improve your craft. We budget for it (hey-o!). Think conferences, online courses and subscriptions, dedicated time away from work to learn something new…it’s really up to you and your manager. We love to see our people grow.  


We offer excellent health, dental, and vision insurance to our US employees, 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, we’ve got you covered!

We also have a Traditional and Roth 401k option. YNAB matches your contributions, up to six percent of your paycheck. Matches vest immediately. (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.) 

We also offer generous paid parental leave for all full-time team members. Here’s to increasing the world’s budgeters, one child at a time!

Competitive Compensation

The starting on-target earning for this position is $150,000+ with an uncapped commission plan. You win and we pay you for your success—yay!

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!) 
  • The bucket list really helps in deciding what we should give you for your birthday and the holidays.
  • We’re all adults. There’s no need to punch a clock, or ask for permission to take off early one afternoon to go see the doctor. We look at what you accomplish, not how long you’re in front of a computer.
  • We’re currently trialing a four-day work week. For us, this means four regular days of work followed by a three-day weekend. Though for this role, particularly with travel, it’s possible there will be weeks where a fifth day is needed. This is new to us, and we're learning a lot, but we're excited about what it could mean both for the company and our team members.  
  • 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 much, but then a few months down the road you’ll realize it’s made your job really, really enjoyable. Don’t underestimate this one!

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.

You, Our New National Sales Director

In this position, you’ll do things like:

  • Work hand-in-hand with our marketing and leadership teams to discuss goals, prioritize projects, and execute on sales strategy
  • Proactively research, qualify, and cultivate new leads and markets for Financial Wellness by YNAB 
  • Utilize phone, email, in-person events, and outbound marketing campaigns for direct prospect and customer communication
  • Present YNAB products’ technical features and benefits as they relate to solving prospective customers’ problems 
  • Prepare, issue, and follow through on proposals and quotes for prospective customers
  • Establish, develop, and maintain positive business relationships and communication throughout the entire sales cycle
  • Join forces with our amazing support team to create a smooth handoff between sales and implementation
  • Utilize a sales automation tool or CRM to ensure we have up to date information on all prospects and customers 
  • Facilitate marketing efforts by regularly communicating discovered needs, trends, beneficial events, and other market intelligence
  • Communicate, explain, persuade, explore and otherwise get all the things done in asynchronous formats. Yes, we like talking to each other in real-time, but as a remote team, much of our collaboration is asynchronous and written.

You’re our person if:

  • You’re a humbly confident sales professional with at least five years of experience.
  • You’re not only undaunted but excited about the above list of responsibilities, and are appropriately self-assured in your ability to tackle most of them.
  • You have the ability to think strategically and long-term, and turn that thinking into tactical progress.
  • You’re a collaborative team player, but are also comfortable working independently with lots of autonomy.
  • You organize things in your sleep and enjoy making sense of chaos, but you’re also comfortable living in spots where messy is THE place to be.
  • You have excellent verbal and written communication skills. You strive for accuracy, intentionality, and integrity in every interaction.
  • You display positive persistence, optimism, and empathy at every turn. You like to find ways to say “yes” to people. 
  • You have excellent problem-solving and decision-making skills. 
  • You’re totally comfortable with being one of the faces of YNAB. You’re confident you’ll be able to internalize our brand, marketing strategies, and support ethic in no time.
  • You value pragmatic solutions based on sound judgment.
  • You have a healthy relationship with failure, and view it as necessary for growth. 
  • You can listen to ideas, questions, and critiques from teammates with grace and patience—not because that’s nice, but because you see this as critical to our shared success.

How to Apply

  • Apply below by 11:59pm PT on Sunday, October 16, 2022. Firm. It’s a real deadline. The kind you love.
  • Attach a PDF of your cover letter. In your cover letter:
  • Introduce yourself and explain why this position is of interest to you, and why you would be a great fit. Please limit this to one page.
  • Attach a PDF resume.
  • Our goal is to make the hiring process as accessible as possible. If we can help you with an accessibility need, email us at accommodations@youneedabudget.com and indicate in the subject line that you’re applying for the National Sales Director position. (Please note that this inbox is only monitored for messages related to accommodations.)
  • Though we know it is customary in some areas, we’d prefer it if you didn’t share a headshot in your application materials. Thank you!

We’re excited to hear from you!

P.S. We'll send you a confirmation email once you apply. Please add that email to your safe sender list to ensure that future emails come through. (If it’s not there, be sure to check your spam or junk email folder.)

P.P.S. If you’re not interested in this position right now, but know someone who might be, we’d appreciate you passing this along!

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We're Hiring a Humbly Confident National Sales Director