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Basecamp Director of Operations

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Headquarters: Chicago IL
URL: http://basecamp.com

Basecamp is hiring a director of operations to run the team responsible for all our technical infrastructure. Our suite of applications is served from a mix of our own servers in leased data-center space and cloud setups in Google Cloud and AWS. The job is to ensure that everything runs smoothly, the lights stay on, and we’ve prepared for bad luck with good planning.

This is a role for someone with experience running a team at least as big as ours and a multi-million dollar budget. You’ll be managing a team of seven and report to the CTO.

Basecamp is a remote-work company, but you’ll need at least 4 hours of overlap with Chicago time in your normal work-day routine.

We strongly encourage candidates of all different backgrounds and identities to apply. Each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. Basecamp is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career.

ABOUT THE JOB

The most important job for operations at Basecamp is to keep the lights on. If our applications aren’t available, it doesn’t matter how well we’ve designed them, how clever we are at marketing them, or how good our support team is. Nobody wants to buy flaky.

This means thinking carefully about risk, making (and testing!) contingency plans, and expecting the worst. While this invariably invites a certain degree of conservatism, part of the job is also being open to what comes next. We used to run everything on our own machines, now we’re also in the cloud. You will help us weigh the trade-offs and mitigate the risks, while moving us forward.

While ops is the second biggest team at Basecamp (after customer support), it’s not so big you won’t have to get your hands dirty. This is a technical role as much as a managerial one. And we expect that you have a broad range of technical chops. Enough such that participating in an on-call rotation does not frighten you (because you will be part of it!). To manage the work at Basecamp, you need to know the work and do the work.

Here are some examples of what you might be working on:

Prepare for the future

Propose a strategy for how we best serve our large, unsharded databases for Basecamp in the cloud. This could include benchmarking instances, working with consultants like Percona, and validating assumptions with the cloud provider.
Coordinate a cloud storage migration to move a couple of petabytes of data from Google to Amazon. Clarify how we verify that everything has been copied, how we may move back, and validating the resilience design. Work with our Security, Infrastructure & Performance team to have programming changes made to the application logic.

Mitigate downtime

Prepare a schedule of regular fire drills for fail-overs between cloud storage regions or applications on our multi-data center setup.
Wake up at 4am to act as incident lead on an outage, then write up the incident report and remediation analysis. Also, considering what lessons need to be incorporated into our crisis handbook.
Be available during evenings and weekends for occasional preventative maintenance.

Team management

Conduct a 1:1 with an ops team member, discussing long-term career progression and short-term goals.
Run a weekly team call and to discuss upcoming and ongoing work.
Write a detailed heartbeat explaining the progress within ops over the last six weeks and a detailed kickoff explaining what’s coming up in the next six.

A lot of the work on ops is reactive: dealing with an outage, setting up a new application, addressing a security vulnerability. And you’ll have a great team of veterans capable of dealing with much of that. Your job in addition to dealing with the day-to-day is to deal with what comes next.

We'll be looking to you to clearly define the roles within the ops team, build clear lines of accountability, set targets for our systems (should we be chasing 5 9s?), balance the reactive work with project work, and ultimately instill a resilience culture at Basecamp. It's not just managing the work, it's also bringing the vision of what the work should be.

This is a lot of responsibility and a high degree of criticality. Basecamp’s existence quite literally depends on the ops team’s ability to keep the servers running and the services available. But that’s only all the more reason that you know how to do this work while keeping and working calmly.

ABOUT YOU

Basecamp is a company of moonlighting managers. While you’ll be responsible for a sizable team, we’re not looking for a micromanager or a chief whip. Everyone at Basecamp is here to do the best work of their career, so we work on systemic problems and try to avoid individual blame.

We’re looking for a clear systems thinker. Someone who reads a story about the intern dropping the production database and wonders not “what an idiot” but “how was this possible in the first place?”.

At the same time, you must be willing to own the concept of keeping the lights on. Unless you’re specifically raising the alarm to signal otherwise, we’ll expect that you have what you need and is able to do what needs to be done. Someone who thrives on a high level of autonomy and responds with a high level of accountability.

We value people who can take a stand yet commit even when they disagree. We subject ideas to rigorous debate, but we remember that we’re here for the same purpose: to do good work together. Charging the trust battery is part of the work.

Yes, you'll need to learn how we work at Basecamp, but we're also looking for someone to teach us how to work. And once we've figured that out, be able to share that story with the world. There's no reason Ops at Basecamp can't have a public profile like we do with programming or design. You'll help us build one.

What we're not looking for is a superhero who might be able to put out five fires burning at once by working 80+ hours/week, but a candidate who avoids the drama by following sound building codes, performing regular inspections, and responding to incidents with a tight routine.

ABOUT OUR PAY AND BENEFITS

Our pay is within the top 10% of the industry, for the matched role and experience, based on San Francisco rates. This comes to a range at hiring of between $280,000 and $350,000, depending on your seniority and qualifications. No matter where you live.

Our benefits are all aimed at supporting a life well lived away from work. None are about trapping people at the office or cajoling them into endless overtime. Just the opposite. We’re all about reasonable working hours, amble vacation time, summer hours, fitness, wellness, food, education, and charity. See the full list.

HOW TO APPLY

Please send an application tailored to this position that speaks to us. Introduce yourself as a colleague. Show us that future. We value great writers, so take your time with the application. There’s no prize for being the first to submit!

We’d like to hear about how you’d approach some of the example projects outlined in the description about the job. Imagine you’re doing the work and walk us through your thinking.

All that being said, don’t send in a copy of War & Peace. We hire rarely at Basecamp, so when we do, there’s usually many applicants. Be kind to the people doing application triage and keep your cover letter to fewer than 800 words and the thoughts on project approaches below the same ceiling (for a total of 1600 words max).

Go for it!

We are accepting applications for this position until June 7th, 2019. We’ll let you know that we’ve received your application. After that, you probably shouldn’t expect to hear back from us until after the application deadline has passed. We want to give everyone a fair chance to apply and be evaluated.

We can’t wait to hear from you!

To apply: https://basecamp.workable.com/jobs/1025288/candidates/new

Posted Basecamp Director of Operations on May 31, 2019 via