Head of Engineering, Enterprise

Visa Hunt; San Francisco (CA); Hybrid; USD 150,000 - 210,000; Full time

Benefits offered by this job

Equity on employee-friendly terms

Health, dental and vision (US)

401(k) with up to 4% match (US)

Flexible time off and holidays

Relocation reimbursement to SanFrancs

High-spec laptop and gear

Regular team events and off-sites

Parental leave (16 weeks)

Job summary

Wispr is building a voice interface platform with a growing enterprise footprint. We are seeking leaders who can close multi-million dollar enterprise deals, understand admin requirements, and advocate for customers while scaling the team and roadmap.

You will work with a small, high-caliber team, with SF-based in-person collaboration and remote-friendly roles across the US. Strong product understanding and negotiation skills are essential.

Qualifications

• Experience selling to large enterprises and negotiating complex contracts.
• Ability to translate admin requirements into product outcomes.
• User-obsessed approach with customer-facing credibility.

Responsibilities

• Develop and close Enterprise-first strategies and SLG deals.
• Represent Wispr to customers and negotiate outcomes.
• Build a credible, hiring-capable team to scale onboarding.

Skills

Enterprise sales

Negotiation

Customer empathy

Tools

Python

PostgreSQL

WorkOS

Temporal/SQS

AWS

React/TypeScript

Job description

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.

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.