Keeper Tax

TurboTax for gig workers

Senior Operations Manager

$110k - $110k / 0.25% - 0.25%
San Francisco, CA
Job Type
Any (new grads ok)
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David Kang

About the role

The reason Keeper Tax exists is simple: every 1099 freelancer deserves an affordable, personal bookkeeper. No one should have to figure out taxes on their own, or overpay the government when they’re barely scraping by. As the Senior Operations Manager, your role is to deliver on this promise to each of our users, alongside our product and technology. This is one of the highest impact roles within our company, and comes with a ton of responsibility at the strategic level.

Managing a cyborg system

Keeper Tax is built on a human-in-the-loop system. We deliver value to our customers through a combination of automation and real human interaction. Every day we send out 30,000 text messages, and we've developed a complex system for fielding the user replies. Your role is to keep this delicate machine humming along, while constantly finding ways to improve it. You’ll have support from the engineering and leadership team as you develop your own operations roadmap. This is also a technical role - every decision should be informed with data and driven by clear metrics.

Remote-first people leadership

We employ a team of remote freelancers working in a variety of customer-facing roles, from bookkeeping to email support to tax filing review. It’s by far the largest team at Keeper Tax. As our Senior Operations Manager, this entire team will all report to you. You’ll have the latitude to choose your personnel, determine their responsibilities, and define the customer experience culture. This is a role for someone who can grow quickly into a mature leader.

User empathy

Every one of our users is someone who was struggling with their taxes when he or she signed up. Our product delivers significant value when it’s working properly, and our users develop a real relationship with Keeper Tax. You’ll be in the driver’s seat for much of this action. We’re depending on you to be an advocate for our users. If they need something that we’re not delivering on, we expect you to proactively push for change.


  • You have an eye for details. This is not a role for someone who just wants to get things ‘roughly right’
  • You have the ability and eagerness to lead a large, remote team
  • You are a strategic thinker. You’re constantly looking for ways to make things better, and you’re proactive in pushing for changes
  • You are calm under fire. This is a role where high-stress situations may occasionally happen. You thrive under such conditions, and aren’t afraid to tackle these challenging moments head on

Compensation & benefits:

We offer competitive cash and equity compensation levels against other Series A companies.

As for benefits, we offer the standard package - health, dental, vision. The only thing we don't currently offer is 401k matching.

When it comes to perks, we subscribe to the No rules, rules! mantra. Each employee gets a personal spending card - whether it's lunch on a workday, a new monitor, or an external consultant, you should get yourself whatever you need.

How to apply:

Please reach out to

At Keeper Tax, we are committed to creating a work environment that is safe and comfortable for people of all backgrounds, regardless of ethnicity, gender, sexual orientation, age, and national origin. We do this because we believe a more diverse team is a better, more effective team.

Our customer base is highly diverse (much more so than many typical Silicon Valley startups). Gig workers and 1099 contractors come from all backgrounds. We are better able to understand and support our customers when we resemble the people we serve.

Why you should join Keeper Tax

With the rise of gig platforms and the creator economy, more young people are finding themselves getting paid as if they were business owners rather than employees. Keeper Tax is helping this new generation take advantage of business tax deductions. On average, our customers discover extra write-offs worth $6,076 per year!