Head of Engineering, Enterprise

Wispr Flow; San Francisco (CA); On-site; USD 150,000 - 250,000; Full time

Job summary

Wispr Flow is seeking an Engineering Leader to drive enterprise readiness and significantly scale its revenue. The role requires strong leadership to manage engineering operations and build a world-class team.

Candidates should have a proven track record in enterprise environments, focusing on quality and collaboration with product management and sales. The ideal candidate will be hands-on, ensuring alignment with the technical direction and standards required for enterprise clients.

Qualifications

• Proven experience leading teams in a product-focused or SMB environment.
• Consistent track record of delivering under pressure.
• Management experience with a modern approach to engineering.

Responsibilities

• Scale revenue from enterprise customers significantly.
• Partner with PM and Head of Sales to build the team and roadmap.
• Ensure high quality in enterprise engineering deliverables.

Skills

Enterprise readiness

Leadership

Engineering judgment

Team building

Project management

Job description

About Wispr

Wispr Flow is making it as effortless to interact with your devices as talking to a close friend.

Today, Wispr Flow is the first voice dictation platform people use more than their keyboards — because it understands you perfectly on the first try. It’s context‑aware, personalized, and works anywhere you can type, on desktop or phone.

In 2026, in addition to dictation, we're focused on building native actions — an agentic framework that understands you, and works reliably.

We’re a team of AI researchers, designers, growth experts, and engineers rethinking human‑computer interaction from the ground up. We value high‑agency teammates who communicate openly, obsess over users, and sweat the details. We thrive on spirited debate, truth‑seeking, and real‑world impact.

We're grown our revenue +150% every quarter for the last 4 quarters, and have raised $81M from Tier 1 VC firms and other well‑known angels.

What you’ll do

• Scale Wispr’s revenue from enterprise customers over 10x in the next year, into the $x00m ARR range.
• Partner closely with PM and the Head of Sales to build the team, roadmap, and product to achieve our ambitious goals.
• Own enterprise engineering end to end: architecture, roadmap, technical direction, and the bar for quality.
• Hire and coach a world‑class engineering team around you.
• Extend our fledgling enterprise‑readiness layer that unlocks deals: SSO and SAML, SCIM, RBAC, audit logging, an admin console, data residency, and the security and compliance posture (SOC 2, ISO 27001) that enterprise buyers require.
• Build out functionality for teams and companies so that the world’s largest companies get more value out of Wispr by using it together.
• Build tooling for our Sales and Customer Success teams to have the leverage needed to support a massively scaling business.
• Stay hands‑on. You’ll use coding agents to make sure you’re grounded in the codebase and serving as an effective player‑coach.

What we’re looking for

• You’ve led teams from a SMB or product‑led motion into the enterprise before.
• A consistent track record of delivering what you said you’d deliver, under customer pressure and through incidents and outages.
• Real domain instinct. You can see around corners on the problems an enterprise business will hit, and you level up the people around you because of it.
• Management experience, plus the open‑mindedness to rebuild engineering management for the agentic era. We want someone who knows the best practices and is thoughtful about when they do and don’t still apply.
• Engineering judgment. You can assess the quality and velocity of your team’s output, and execute credibly yourself when it’s needed.
• Intrinsic motivation for these problems, and the ability to make other people feel it too, in your team and in the candidates you recruit.

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.