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We're Hiring a Humbly Confident Senior IT Systems Administrator

About Us and Why We’re Hiring

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 buying 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.

For this position, YNAB is looking for an experienced IT professional with a broad technical background to help us with the administration, management, and support of a wide range of internal systems and applications. We want someone who is earnest about tech and finds joy in helping their teammates.

The person in this role will be appreciated from day one, as you’ll be YNAB’s first IT hire! YNAB has been growing steadily, and frankly, we’ve exceeded the point where we need an experienced and skilled tech generalist to help us get the maximum benefit from our internal systems. That’s where you come in!

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 this, you’ll probably like it here, and we can’t wait to connect with you!

Of course, we have some firm* requirements too, like five years of professional experience in some IT capacity.

*Well, firm-ish. If you know you’re a great fit for this role but fall a little short of the five-year requirement, 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.

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

Who You’d Be Working With

Although you’ll be YNAB’s first IT hire, you won’t be alone. You will join our near 50-person engineering group and work closely with our operations team and alongside our senior security engineer. You will also support awesome people from all parts of the organization who all have one thing in common: They are a joy to work with.

You won’t find heated arguments and raised voices here. We all love to solve problems in creative ways, and we regularly take time to geek out and show each other something cool we built or found to make our lives easier. We save our competitive spirit for YNAB’s external competitors (or the occasional lively board game session), but internally we build up our teammates and celebrate their successes.

How You’ll Work at YNAB

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 the last two years. We have a team of truly exceptional people—the kind you’ll be excited to work with. Here’s how we operate:

Responsibility and Empowerment

YNAB appreciates, respects, and trusts the expertise and judgment of everyone in our engineering team, and this role is no different. Everyone is empowered to do what they think is right.

We also work collaboratively. We continuously seek a pragmatic balance between nimble flexibility and unity, structure, and security.

Even though our people are right a lot, it’s okay to make mistakes here. We freely admit when we’re wrong. If something doesn’t go as expected, we learn, bounce back, and make corrections.

You won’t be alone—others will be there to help, review, reassure, and back you up. We own our systems, applications, processes, and collective outcomes as a team.

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. Wherever you are in that region, 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 day. 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.

In this role, you’ll be collaborating with people across many time zones, so depending on where you live, some flexibility in working hours may be necessary to provide overlap for synchronous work. For example, if you’re on Pacific Time, you may need to work some early mornings to help YNAB team members in central Europe.

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 whole team 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, and most recently, Laguna Beach. 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, Lynda/Skillshare subscriptions, books, and dedicated time away from work to learn something new. We love to see our people grow.


We offer excellent health, dental, and vision insurance for 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 salary range for this position is $60,000-$75,000 USD annually, depending on experience. We consider raises every year, and have a bi-annual profit-share bonus. YNAB wins, you win—that kind of thing.

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…every week. 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 will replace it regularly.
  • Did we 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 we want to talk about you. You will play a part in building something that helps millions of people discover budgeting as an essential financial and life-planning tool.

Apply Now

You, Our New IT Systems Administrator

In this position, you’ll do things like:

  • User administration for onboarding, offboarding, and role changes—and devise methods to make this easier.
  • Set up and manage automatic provisioning and sign-on tools based on group membership (e.g., Okta Identity Cloud)
  • Management of the 3rd party tools and software used by all YNAB teammates, such as email, Slack, video conferencing, 1Password, Notion, and Google Workspace.
  • Administration for specific applications and services used by YNAB product development, such as Github, Heroku, Figma, Amplitude, SumoLogic, and Bugsnag, as well as those used by YNAB marketing, such as Facebook and Braze, and those used by YNAB support, like HelpScout, and Kustomer.
  • Troubleshoot any access or performance issues with these systems.
  • Assist teammates in setting up their computers, accessing systems, and configuring particular environments (e.g., a development environment). Serve as the first point of contact to aid with any tech-related issues. Our team is fairly tech-savvy, but there are still plenty of opportunities to help.
  • Participate in equipment purchasing, provisioning, and configuration processes for laptops, peripherals, and one-off software.
  • Maintain an inventory of all the software used by the company, by whom, and for what purposes.
  • Work closely with YNAB’s security lead to ensure security protocols and best practices are implemented and followed.  
  • Work closely with the Operations (HR) team to advise on and plan for all employee-related technical needs and systems. You’ll take a lot of the manual processes we have now, and find ways to streamline or even automate them.
  • Provision and manage security-related systems such as VPNs, Kolide, Cloudflare for Teams, or AWS Identity Management.
  • Edit configuration files and occasionally write a script to help make administrative tasks more manageable.
  • Proactively identify, suggest, and implement new systems and tools that benefit the team.

You’re our person if:

  • You’re an IT professional with at least five years of experience and know your way around managing and configuring modern systems, applications, and tools.
  • You have excellent verbal and written communication skills and enjoy using your knowledge to help others when they require support.
  • You’re process-minded and can make order of chaotic details. You can follow a process like clockwork, innovate when something could be done better, or create a new process from scratch.
  • While process-oriented, you also enjoy facilitation and collaboration, like to find ways to say “yes,” and value pragmatic solutions based on sound judgment more than simple policy enforcement.
  • You know a lot about navigating modern operating systems, have experience with Mac OS, Linux, and Windows, and are acquainted with iOS and Android.
  • While maybe not a developer, you are comfortable with a Unix command line and can write simple scripts and edit configuration files.
  • You may not be a security specialist, but you are aware of how applications, accounts, websites, and services can be exploited. You are security conscious while you work and are protective of company and customer data and privacy.  
  • You have excellent troubleshooting skills and can find problems and devise solutions.
  • You can’t help but notice that things could be done better/faster using this or that method/tool. And then you take the initiative to actually make it better.


YNAB is an equal opportunity employer. We believe a diversity of backgrounds, beliefs, abilities, and experiences is critical to our success. 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, experienced, and diverse team that loves working together to build something that matters.

How to Apply

  • Apply by filling out this form. You’ll need to log in to your Google account to access it.
  • The deadline is 11:59 pm PT on Sunday, July 10, 2022.
  • Our goal is to make the hiring process as accessible as possible. If we can help you with an accessibility need, email us at and indicate in the subject line that you’re applying for the IT Systems Administrator position. (Please note that this inbox is only monitored for messages related to accommodations.)

We’re excited to hear from you!

Apply Now

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 Senior IT Systems Administrator