Head of Engineering, Enterprise

About this role

ABOUT WISPR

We're building the first voice interface a billion people use every day.

Our first product, Flow, lets you talk instead of type anywhere on your computer or phone, and turns messy speech into polished text that is ready to send. It's scaled from $2M → $50M in ARR in under 12 months with millions of users and thousands of enterprise customers. How we think → https://wisprflow.ai/post/the-master-plan

The team is still small enough that every person shapes what gets built.

ABOUT THE ROLE

Wispr Flow got into large companies with pure product love. It's been used organically in 487 of the Fortune 500 and now being adopted enterprise-wide across the largest organizations.

Our Enterprise ARR has been growing 40% MoM (i.e 2x every two months), with hundreds of millions of dollars of pipeline and a clear repeatable motion to make Wispr the default in every organization. A small number of engineers have been carrying all of it alongside everything else - and Wispr has been deployed officially in 12,000+ companies today.

What's next: Large enterprise deployments are blocked on expanded enterprise-readiness. We have a number of solutions we can build and sell on top of our core platform, and we want to build a dedicated Enterprise engineering team to help scale this business. You'd be making those calls while sitting in customer conversations, negotiating scope, and hiring the team that builds it.

You'd work with our CRO, the strategic sellers running these deals, the engineering team, and with our founders, Tanay and Sahaj. We're building this team from scratch - and you get to shape what Wispr for Enterprise looks like.

WHAT YOU'LL DO

- Own enterprise engineering end to end: architecture, product & technical roadmap, technical direction, and the bar for quality.

- Hire and coach a world-class engineering team around you.

- Stay hands on to be grounded in the codebase and serve as an effective player-coach.

- Unblock the F500 deals in front of us now, and scale the enterprise-readiness layer so the next thirty don't have to be unblocked one at a time.

- Turn admin requirements, new products and business-model experiments into one prioritized roadmap, and be able to defend the order.

- Spend real time with customers. Sit in on calls, listen to Gong recordings, and pull what AEs are hearing back into what gets built.

- Be the technical counterpart our sellers bring into the room, with the poise to represent Wispr and negotiate scope directly with a buyer.

- Scale Wispr's revenue from enterprise customers >10x in the next 12 months, into the $x00m ARR range.

THIS ROLE IS PERFECT FOR YOU IF:

- You've built the enterprise layer at a startup before, from the first SSO integration through to broad deployment across a large customer.

- You get a thrill from working with customers and strat sellers to close seven-figure deals.

- You have a handful of people you'd want to call in your first week to build your initial team.

- You're a builder at heart and ship code.

- You've seen enterprise-readiness at different scales.

- You have your own opinion of what a great enterprise-first software looks like.

- You care about velocity, thoroughness, and the balance between the two.

Tech stack: Python, PostgreSQL, WorkOS, Temporal/SQS, AWS, occasional React/TypeScript

LOGISTICS

Location. About 60% of the team is in San Francisco and the rest are remote, mostly US-based.

- If you're in SF: you'll be in the office most days. We think the best work happens in person. Most of the team is here five days a week, and a few do three or four days depending on family or long commutes.

- If you're remote: we're open to remote for some roles. We fly remote teammates to SF for three to four days a month.

Visa sponsorship. We sponsor visas: H1B, O1, EB1, L1, STEM + OPT, and more. We can't successfully sponsor for every role and every candidate, but if we make you an offer we'll make every reasonable effort, and we retain an immigration law firm to help.

WHAT WE OFFER

We're a small, focused team that cares deeply about the quality of our work and the people we do it with. Here's what you can expect:

- Equity on employee-friendly terms, including extended exercise windows and a combination of ISOs and RSUs. Ask us for more details!

- Health, dental and vision. We cover 100% of the premium on the Anthem Blue Cross Gold PPO, and 75% of premiums for dependents. (US only)

- 401(k) with up to a 4% match. (US only)

- Flexible time off and company holidays.

- All meals in the office, plus commuter benefits and relocation reimbursement if you’re moving to San Francisco.

- A high-spec laptop, monitor, and a whisper-friendly microphone.

- Regular team events and off-sites.

- 16 weeks of paid parental leave (12 weeks for non-birthing parent). The early days with a new baby matter more than anything we're doing here, and we want you to be present for them.

We encourage you to apply even if you do not believe you meet every single qualification. Not all strong candidates will meet every single qualification as listed. Research shows that people who identify as being from underrepresented groups are more prone to experiencing imposter syndrome and doubting the strength of their candidacy, so we urge you not to exclude yourself prematurely and to submit an application if you're interested in this work. We’re designing how humans interact with AI, which makes representation even more important, and we strive to include a range of diverse perspectives on our team.

We are committed to ensuring a fair and accessible interview process. If you need any accommodations or adjustments, please let us know.