Humbly Confident Executive Assistant

Lehi, UT, United States Full-time

(*Please note: this is one of the very few jobs at YNAB that's not remote. It will be in our Utah office. More details below.)

At YNAB, we build the world’s best budgeting software. We have an amazing product, and we’re super proud of how we teach people to align their money with their priorities, in turn changing their lives.

We’ve grown quite a bit over the last couple of years (from 20 or so employees to 58) and with our current Executive Assistant taking on a lot of the HR responsibilities, her plate is getting pretty full. This is where you come in. We’re looking for full-time help with a lot of assistant and office admin work. A small sampling: you’d be arranging flights and travel itineraries, planning a yearly company retreat, and finding unique Christmas and birthday gifts for all team members. Yes, you read that right, you get to give presents as part of your job. We have an incredible team of some of the most passionate and friendly people you will ever meet and as an assistant, you get to help make sure everyone has an exceptional work experience at YNAB.

That’s a small taste of what you’ll be working on, but first, you need to know if you’ll even like working with us. (We think you will.)

A Bit About Us

We build the best budgeting software around, YNAB or “You Need a Budget” if you have a lot of extra time on your hands. For more than a decade, people have been buying YNAB and then telling their friends what a difference it has made in their lives. (Google us and you’ll see what we mean.) We love building something that has a huge positive impact on people’s lives.

We’re profitable, bootstrapped, and growing. YNAB started in 2004 and we haven’t taken any outside funding—we’re in it for the long haul.

We have one overarching requirement when it comes to joining our team: our Cultural Manifesto has to really click with you. If you’re nodding emphatically while reading it, you’ll probably fit right in, in which case, we can’t wait to hear from you!

First, let’s talk about life at YNAB and then we’ll go into detail about what we’re looking for.

How You’ll Work at YNAB

We work really hard to make working at YNAB an amazing experience. We have a team full of truly exceptional people—the kind you’ll be excited to work with. Here’s how we operate:

Remote Culture

We’re a distributed team, with people spread all over the U.S. and a handful of international folks as well. Proximity doesn’t influence productivity. As I write this, Taylor (our CTO) is in, London or Brazil, or maybe back in Austin? Not all of us travel so extensively, but the fact that he does is totally okay because we’re all adults (except for Jesse’s kids, that do menial office work). Three of us work in an actual office in Lehi, UT, and that’s where this position will work from as well.

No Crazy Hours

We rarely work more than 40 hours per week. There have been a few occasions where things got a little crazy and people had to log some extra hours. 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; no need to go crazy on the hours.

Take Vacation (Seriously)

We want you to take vacation. In fact, we have a minimum vacation policy of three weeks per year (plus two additional weeks for Christmas break). It’s important to get out and do something. We’ll look forward to seeing pictures of your vacation in our internal chat room, creatively named #office_wall.

The YNAB Retreat

We get the teams together once a year to catch up on spreadsheets and powerpoints in a Best Western conference room. Just kidding. This year it was a beach house in the Outer Banks. Last year was at a gigantic cabin in the mountains. The time before that it was in Costa Rica.  We do really fun things, but the highlight is always just hanging out together and having a blast. (You’ll actually play a BIG role in pulling these retreats off!)

Up Your Game

We’re serious about helping you improve your craft. You can speak up and let us know you’d like to take on a project that scares you (and us!).  


We have fantastic 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, no big deal, we’ve got you covered!)

We also have Traditional and Roth 401k options. YNAB contributes three percent whether you choose to throw any money in there or not. It vests immediately. (Are you a personal finance junkie like 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. You’re not a PF junkie? Then trust us, it’s great.)

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 helps in deciding what we should give you for your birthday and Christmas: No gift cards here. We tried that. Super boring.
  • We have a bonus plan based on profitability. You’ll be in on that from day one. YNAB wins, you win. That kind of thing.
  • 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 (health insurance premium 100% covered!). We look at what you’re accomplishing, not how long you sit (have you tried standing?) in front of a computer.
  • 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 I mention we make 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 I want to talk about you. You will play a big part in helping our team members have an exceptional experience working at YNAB.

Who you’d be working with:

Everyone at YNAB works remotely, except for three of us in the Lehi office. (Actually, it’s a cute old house that we turned into an office. Very quaint.)  You’ll certainly rub digital shoulders with the whole company, but we’d love for you to join the three of us in the office: 

Caitlin is our current Executive Assistant and is starting to run the ship on more and more HR stuff. You’d be the one taking a lot of things off her plate. She’s a master at travel logistics, keeps all of us on schedule, and can keep a hundred plates spinning without dropping a single one. Her happy place is on the beach (preferrably Maui), and she can teach you how to travel hack your way to free flights all over the U.S. Oh, and she’s having her first baby this fall (so excited for you Caitlin!) so we’ll need your help filling her shoes while she’s on maternity leave.

Chance is our COO and gets to obsess about building a great company and making sure that people really love their work at YNAB. He has the best job in the world. When he’s not with his family outdoors, you can find him on a golf course, tennis court, or trying to shoot a steel gong from 1,000 yards away.

Jesse’s the CEO and founder of YNAB. He’s super stuffy, wears a suit constantly, and is really good at barking out orders. Just kidding. Read the Cultural Manifesto and you’ll get a pretty good feeling for Jesse’s personality. He cares deeply about YNAB and the people making it a success. Don’t let the workout clothes fool you, this guy knows his stuff.

I think you’ll find that everyone at YNAB is a joy to work with. It’s truly remarkable. The YNAB Team cares about each other. Really cares. We’re a really happy team and we sincerely want you to be happy too.

Now, back to you, our new Executive Assistant…

This role is a pretty good mix between an Executive Assistant and an Administrative Assistant. You’ll do a good amount of work directly for the executive team, but you’ll also stretch far beyond that in your responsibilities for the whole team. Looking into my crystal ball, I have pretty good picture of who you are:

You’re really good at what you do:

  • You anticipate and prepare for contingencies as if you’re psychic.
  • You could write a book on getting things done.
  • You never drop the ball. Well, maybe not never, but the last time was in 2007.
  • You’re very proficient with technology. You’re comfortable learning new things, and do so quickly.
  • You can’t help but notice that things could be done better/faster using this or that method/tool.
  • You have years of experience as the executive assistant of c-suite executives.
  • You’re comfortable with big, important projects, while knowing that no one is too big to do the small stuff. Like taking out the trash at the YNAB house. Or at least telling one of Jesse’s kids to do it.
  • You are incredibly organized, flexible, and collaborative.
  • You never met a deadline you didn’t love.
  • You are self-motivated and driven by nature, maybe even a little competitive.
  • You have the ability to stay laser-focused on the big picture, without losing sight of every. last. detail.
  • You are wildly productive and independent, but a team-player at heart.
  • You aren’t afraid to experiment, even if it means chalking mistakes up to learning from time to time.
  • You do well with vague directions but aren’t afraid to ask questions.

But maybe you’re also ready for a change. After all, at your current job:

  • Because your boss is so busy,  you are also extremely busy, and feel like maybe you could use an assistant (or two).
  • You can’t ever “turn work off.” You are pulled in lots of directions on any day of the week, at any time. (We’ll change this when you come on board over here! We are serious about work-LIFE balance.)
  • You’re feeling pretty burned out and are looking for something with a bit of a steadier pace. (We’re still growing rapidly, and you’ll be stretched, but we have our priorities straight and don’t love work for its own sake.)
  • You love your boss, but you’re ready for a change. 

We love all those things about you, that you’re super organized, proficient, skilled, and maybe even psychic. But for those that aren’t total psychics:

Here’s what you’d be responsible for:

  • You’ll handle all logistics for travel, not only for the execs, but the whole team when needed. People travel for quarterly meetings, conferences, team meetups, interviews, and of course, our annual retreat. You’d be booking all flights, creating travel itineraries, coordinating transportation, hotels, conference rooms, food, and the like. All while making it seamless and easy for the person actually traveling.
  • That annual retreat mentioned above? Yeah, you’ll play a big part in planning that and making it an incredible experience for the team. It’s kinda like planning a three-day wedding. Together with Chance & Caitlin, the retreat will be your baby. And trust us, the bar is pretty high.
  • You’ll handle the calendars of some of the execs and schedule interviews.
  • You’ll be in charge of getting thoughtful and unique birthday and Christmas gifts for the team (all 58 of them).
  • We celebrate when people join the team and you’ll be in charge of this. It looks something like you sending a package with a t-shirt, a gift card to their favorite restaurant, and a note from the entire team telling them how happy we are that they’ve joined. You’d want to make sure the package arrived on their first day, guaranteed.
  • When we start our bucket list initiative, you’ll help team members cross items off their buckets lists. I know, that sounds weird, but we are committed to helping team members do great stuff outside of work.
  • You’ll help wherever you can by wrapping presents, grabbing the mail, running errands, shipping t-shirts, buying supplies, and figuring out the best way to frame a jigsaw puzzle that’s so hard we’re scared to move a single piece.  
  • And on your best days you help find opportunities to wow team members or make their day at work that much better. You’ll become a bit of an evangelist of the YNAB work culture and really help bring it to life with your personality and also some ideas that you’ve brought to the table.

We envision this being full-time work at 40 hours/week. We’d like your schedule pretty set as far as being at the office at certain times. We’re also happy to have you work from home occasionally, or come in later, or earlier, or whatever. The overarching principle is that you’re doing great work, and helping others do their best work.

Bonus Points:

  • You already use and love YNAB.

How to Apply

  • Write a cover letter (attach PDF) to introduce yourself and explain why this position is of interest to you, and why you would be a great fit. Cover letters are meant to sell, so sell us!

  • In your cover letter, answer the following:

  • Hypothetical, but real situation: Todd is our Chief Customer Officer. He needs to meet with three candidates for three open support positions. We always meet with promising candidates face to face. We’d like to meet with all of them before July 15th. Todd lives in Boston. Candidates A, B, and C live in Chattanooga, TN, Sacramento, CA, and Philadelphia, PA respectively. Candidates can fly to Todd, fly somewhere central, or meet with Todd face-to-face. Organize an itinerary for Todd with everything he'll need to know to make it a seamless experience for all involved (you can use real data, or make stuff up).
  • Attach a resume (PDF). If you don’t have a resume because you aren’t even sure you’re looking to change jobs, that’s fine! An informal list of your work and education history are all we’re looking for.
  • Note: Please do *not* use the "Apply with LinkedIn" option. 

The deadline for applications is 11:59PM on June 25th, 2017. Firm. It’s a real deadline. The kind you love.