Reasons not to join On Deck

If you were to join On Deck, we’d want you to really love it. We also know that it can be hard to tell from the outside looking in whether that would be the case for you. So, we challenged ourselves to come up with an honest set of reasons someone wouldn’t want to join our company. We hope it helps you make an informed decision about whether On Deck is a place you’d love to work.

1. Another company’s mission would get you way more fired up

On Deck is on a mission to help ambitious builders and makers accelerate their ideas and careers. We believe this work is good, important work, that facilitates economic growth and expands access. We want to work with people who believe that, too. There will be times when the company or community requires something of you that feels outside your skillset, out-of-scope for your job description, or frankly just not that fun. The most satisfied, most impactful members of our team do them anyway because they believe that progress towards our mission, and the success of our members, is their success. They take pride and derive satisfaction in putting the needs of the company and community members before their own.


Am I particular about how, where, and when I’m willing to contribute? Is there another flavor of work I think I should be dedicating my time and energy to right now? Is a critical tweet here and there likely to change your personal relationship with your company or your work?

2. You want a 9-5 job

We work entrepreneur-style at On Deck. We don’t mean sleeping under your desk or not being able to make it to the dinner table for time with loved ones, but you should expect to work more than the standard 40 hrs/week at some odd times. We think about hours, schedules, and commitments in terms of work/life blend more than work/life balance. Depending on your role, you might be supporting a community or collaborating with team members that span multiple time zones. Something urgent and important may come up that causes some last-minute calendar Tetris. Many members of the OD team find the flexibility an advantage of working at On Deck, because it means they can manage their work schedule to the ebbs and flows of their energy and personal life. Need time away from Slack? Set your status and shut it down. Need to pick your kid up from school? Go for it. Want a work block for focus time but there’s that one 15 min catchup smack in the middle of your 3-hour opening? Ask your colleague to move it; they won’t mind. We don’t evaluate performance based on facetime or hours worked; just that the work gets done and done well.


Would you be willing to have a recurring meeting on your calendar after 5pm? Does it bother you to get a Slack message on a weekend? If you get a work message when you’re not working, are you annoyed at the person who sent it, or yourself for checking work messages when you’re not supposed to be working?

3. You do your best work in highly-structured, steady-paced, meticulously-planned environments

The work at On Deck can oscillate between highly collaborative and highly independent, big picture thinking and in-the-weeds execution, contemplating strategy and maniacally shipping. Depending on your role, phase of project, or company needs, you might even get all of that in a single day. The people who find the work at On Deck most enjoyable like making their own to-do list and then getting everything on it done. They seek support, not supervision. They like solving their own problems and, when they need support or think it would accelerate the pace or impact, they ask for what they need proactively. We hire a lot of entrepreneurs and former founders.


When something comes up unexpectedly requiring your attention, do you feel bogged down? Is shipping something when it’s great, but perhaps not perfect in your eyes, a dealbreaker? Do you prefer to rely on your manager to help you decide what to work on and how to work on it?

4. You like finding and poking holes more than you like filling them

We are a lean team of caring, motivated, and hard-working problem-solvers. If something’s broken, you don’t need permission to fix it. Our highest-impact team members run towards challenges, not away from them. They have a knack for sniffing out the highest priority work, and getting it done with relentless determination and focus. This also means identifying and acknowledging what low priority work isn’t going to get done right now, while the focus is on bigger things. We’d always rather have it done sooner than later. We hire people who find it more interesting and satisfying to implement solutions today, not talk about problems and how they can be solved tomorrow.


Do you dislike being in the weeds when the weeds are really thick and maybe a little thorny? If you noticed the emperor wasn’t wearing any clothes, would you bring him some pants?

5. You see differences as divisions

On Deck is, and always will be, a welcoming home for people across every spectrum of identity. It’s unlikely that you’ll agree with the political or social views of every On Deck employee or community member. That’s a feature, not a bug. In fact, we seek it because we want to foster a culture that facilitates the free exchange of information and ideas, leave room for experimentation, taking risks, and making some mistakes. We see openness, vulnerability, and discourse as a requirement for that environment. We also see those who share ideologies and engage in behavior with the intention to alienate or judge as a threat to that environment. Our most effective team members are inclusive thinkers, warm operators, and measured communicators. They seek to bring people together, default to trusting others, approach differences of opinions with curiosity, and can disagree without being disagreeable. They show up to every interaction with respect and kindness, especially when faced with ideas and opinions that might conflict with their own. We don’t aspire to be a company of robots, but we do want to work with people with the maturity and presence to be both human and professional.

Borrowing from our friends at a16z, we don’t have quotas or goals or objectives to be diverse — we have a goal to be the most talented company in the industry and we end up being diverse as a result of that goal. Given our focus on expanding access, we focus on quantity and outcomes, not on percentages (i.e. equitable), and aim to put more people from all backgrounds in business than any other venture firm in the world


If you learned that one of your colleagues had different political leanings, would you still be as enthusiastic about working together? Do you shut down or get heated when faced with a difference of opinion? What about when you really, really disagree with that opinion? Are you supportive of a16z’s values around embracing differences (outlined here, in the ‘we are all different’ section) and Stripe’s value around maintaining neutrality (outlined here in the ‘Stripe Service’ section)? (We are). Do you unequivocally believe in free speech? (We do).

6. You believe that something has to be exclusive for it to be cool

If we’re wildly successful, anyone with ambition, passion, and an idea will have a home somewhere in the On Deck community and ecosystem. “Gatekeeping” is an anti-goal. The majority of our team and community members have felt like an outsider at some point in their lives and/or work, and find joy in extending warm invitations to join our world. We're excited to welcome many, many ambitious and talented people into our company and community (in-line with our goal that every new member adds value). We take pride in our belief that access to a quality community doesn’t have to be zero-sum. In fact, we’re on a mission to make sure it isn’t!


Does extending invitations liberally (albeit thoughtfully) sound lame to you? Are you disinclined to like something simply because it’s popular? Are you supportive of and/or energized by others building in public and thinking out loud?

Big thanks to Brie Wolfson from The Kool-Aid Factory for being an incredible thought partner and helping us define our operating principles and non-values.

Careers at On Deck

We have some pretty lofty ambitions. And to get there, we need the most talented folks on the planet to join us in our pursuit.

We’re a fully-distributed team operating across 14 timezones.

Interested? Check out our careers page to learn more!

Want to work with us?

Our careers

Our Team

We’re like a high-performing sports team: we form meaningful bonds with each other and are here to win together. Our team is highly entrepreneurial, with many members having experience as founders.

If you want a job that pushes you to do your very best and continually learn, On Deck might be the place for you.

Say hello!

Meet our team