Head of Engineering, Enterprise

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 → The team is still small enough that every person shapes what gets built. What would happen in 3mo if you join? Major deals with Fortune 100s get unblocked We have a clear prioritized roadmap for Enterprise features based on admin requirements, new products we’re selling them, and support business model experiments Our strat team feels like they have a partner to help close multi-million dollar deals We have a solid team of engineers to build these systems out to scale for F500s What would need to be true to get to these outcomes? You understand the different flavors of enterprise requirements deeply and their pros and cons (to prioritize and negotiate them) You are user obsessed and spend time with customers, listening to Gong calls, and learning from AEs about feedback and blockers You have the poise and authority to represent Wispr in front of customers and negotiate with them You have a group of people that you would hire immediately You should be a first principles thinker + opinionated on how to build a great Enterprise serving What is okay to not have experience in? Okay if missing some areas like MDM / desktop app experience etc Okay if not great at UI / frontend / design sense Okay if no consumer / PLG background What would you need to have already done? You have taken star talent with you before to a new role You have seen a successful Enterprise-first SLG business and worked with top tier AEs You have had to prioritize a roadmap You still active build - necessary to build credibility for hiring A+ talent You have startup experience, particularly in scaling enterprise platforms from early adoption to broad deployment 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.

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