Head of Engineering, Enterprise

Wispr Flow

• $160K — $200K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in engineering leadership roles with experience scaling from SMB to enterprise
  • Proven track record of meeting ambitious goals under pressure
  • Strong intuition for enterprise-level challenges and customer needs
  • Experience in rebuilding engineering management with modern practices
  • Sharp engineering judgment on team output and quality
  • Ability to inspire and motivate teams around complex problems

Responsibilities

  • Scale enterprise revenue significantly, targeting over 10x growth within the year
  • Collaborate with Product Management and Sales leader to shape team and product roadmaps
  • Oversee end-to-end engineering for enterprise offerings, including architecture and quality standards
  • Recruit and mentor an elite engineering team to meet high standards
  • Develop essential security functionalities to meet enterprise needs like SSO, audit logging, and compliance
  • Enhance collaborative features for large teams to maximize software value
  • Create supportive tools for Sales and Customer Success teams to enable rapid business scaling
  • Maintain hands-on involvement in coding to guide and support the team effectively

Benefits

  • Dynamic work environment with growth opportunities
  • Support for ongoing professional development and training
  • Health, wellness, and work-life balance initiatives
  • Opportunity to lead impactful projects in a fast-paced setting
  • Flexible work arrangements to foster a productive culture
Full Job Description
About the role

You'll build and lead the engineering team responsible for Wispr's Enterprise product. You'll work directly with customers and GTM, decide what belongs on the roadmap, and turn complex requirements into capabilities that unlock major deployments without compromising the broader product.
What you'll do
  • Build and lead a high-throughput Enterprise engineering team
  • Own and ruthlessly prioritize the roadmap across admin, security, platform, and new products
  • Work directly with IT leaders and buyers to uncover the real problem behind each request
  • Turn urgent deal blockers into durable product capabilities
  • Represent Wispr with technical depth and authority in high-stakes customer conversations
  • Stay close enough to the code to set direction, unblock the team, and earn technical trust
You may be a fit if
  • You've taken an enterprise product from early adoption to broad deployment
  • You've personally worked with Fortune 500 buyers, IT teams, and top-tier sales organizations
  • You've owned both what gets built and the engineering team that builds it
  • You can push back on a customer request while offering a better path forward
  • You've recruited exceptional engineers who would choose to work with you again
  • You still build and lead through technical credibility


Consumer growth, ML, voice, and experience with every enterprise platform are not required.
Get to know us
  • Our Series B
  • Advancing HCI
  • Introducing Wispr Advanced Interfaces Lab
  • Technical challenges behind Flow


Logistics

We sponsor H1B, O1, EB1, L1, STEM OPT, and more. We can't guarantee sponsorship for every role, but if we make you an offer we'll make every reasonable effort, with help from our immigration law firm.

We strongly encourage you to apply even if you don't meet every qualification. The strongest candidates we meet rarely do, so don't exclude yourself prematurely. We're rethinking how humans interact with AI, and doing that well demands diversity of perspective and experience.

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

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