Software Engineering Manager (AI Quality)

WHOOP
Boston, MA
On-site

Who this role is best for

Best suited to mid-level engineering managers with AI/ML expertise who thrive in wearable technology environments and can relocate to Boston.

Best fit for

  • Engineering managers with a track record in AI quality and vendor management.
    — “Proven experience managing third-party vendor relationships and technology partnerships.
  • Technical mentors comfortable guiding teams in high-stakes AI architecture decisions.
    — “Providing clear technical direction and documenting the rationale for high-stakes AI architecture choices.

Things to consider

  • Relocation to Boston is mandatory for this position.
    — “The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office.
  • Equity is a significant component of total compensation.
    — “At WHOOP, we view total compensation as the combination of base salary, equity, and benefits.

How to stand out

  • Demonstrate concrete examples of improving AI model reliability at scale.
    — “Experience managing an AI product at scale is a plus.
  • Highlight leadership in fostering innovation and psychological safety within teams.
    — “Foster a culture of innovation, teamwork, psychological safety, and continuous learning.
  • Showcase experience with wearable technology or health-related AI applications.
    — “Passion for wearable technology and experience thriving in a fast-paced, high-growth environment.
Pace · Fast PacedCollaboration · HighAutonomy · MediumDecision Impact · TeamLevel · Senior

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • lead AI quality team
  • establish rigorous testing frameworks
  • manage third-party vendor relationships
Typical background
5+ years software engineering experienceAI/ML product management

Skills & requirements

Required

Software EngineeringAi/mlTeam ManagementTechnical Leadership

Preferred

Wearable TechnologyFast-paced Environment

Stack & domain

AIMLSoftware EngineeringLeadershipCommunicationTechnology

About the role

Original posting from WHOOP via Ashby

At WHOOP, we're on a mission to unlock human performance and healthspan. WHOOP empowers users to perform at a higher level through a deeper understanding of their bodies and daily lives. Our wearable device tracks key physiological metrics such as heart rate variability, resting heart rate, and sleep quality to provide personalized insights into fitness, health, and recovery.

The AI Quality team at WHOOP is responsible for ensuring the reliability, performance, and integrity of the AI models that power these insights, delivering cutting-edge AI technologies that our members can trust.

As an Engineering Manager at WHOOP, you will have both technical and people management responsibilities. On the technical side, you will partner with product and engineering leaders to uphold our "Measure What Matters" principle, ensuring every AI initiative has clear, visible, and actionable metrics. You will guide a team of AI and ML engineers in developing robust technical designs, architecture, and operational excellence. You will embody our "Decisions Over Consensus" principle, providing clear technical direction and documenting the rationale for high-stakes AI architecture choices.

On the people management side, you will foster a culture of innovation, teamwork, psychological safety, and continuous learning, ensuring all team members feel empowered to do their best work.

RESPONSIBILITIES:

  • Lead and manage a team of cross-skilled engineers responsible for measuring and improving the quality of AI outputs.
  • Champion the "Measure What Matters" principle by establishing rigorous testing frameworks to evaluate model drift and performance.
  • Exercise "Decisions Over Consensus" to provide clear technical direction and resolve alignment stalls for the team.
  • Manage third-party vendor relationships, overseeing both technology integration and partnership performance.
  • Define technical strategy, architecture, and design for AI quality.
  • Drive continuous improvement initiatives to optimize engineering productivity and quality.
  • Provide mentorship and coaching to team members to support their professional growth.

QUALIFICATIONS:

  • 5+ years of experience in software engineering, with significant experience building and measuring the quality of AI/ML products.
  • Proven experience managing third-party vendor relationships and technology partnerships.
  • Strong technical skills in Applied AI, Machine Learning, and software deployment lifecycles.
  • Excellent communication, interpersonal, and people management skills.
  • Passion for wearable technology and experience thriving in a fast-paced, high-growth environment.
  • Experience managing an AI product at scale is a plus.

Learn more about our Software Org and how to be successful in your engineering career at WHOOP via our Career Framework https://engineering.prod.whoop.com/careerframework.

This role is based in the WHOOP office located in Boston, MA. The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office.

Interested in the role, but don’t meet every qualification? We encourage you to still apply! At WHOOP, we believe there is much more to a candidate than what is written on paper, and we value character as much as experience. As we continue to build a diverse and inclusive environment, we encourage anyone who is interested in this role to apply.

WHOOP is an Equal Opportunity Employer and participates in E-verify https://www.e-verify.gov/ to determine employment eligibility.  It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

The WHOOP compensation philosophy is designed to attract, motivate, and retain exceptional talent by offering competitive base salaries, meaningful equity, and consistent pay practices that reflect our mission and core values.

At WHOOP, we view total compensation as the combination of base salary, equity, and benefits, with equity serving as a key differentiator that aligns our employees with the long-term success of the company and allows every member of our corporate team to own part of WHOOP and share in the company’s long-term growth and success.

The U.S. base salary range for this full-time position is $150,000 - $215,000. Salary ranges are determined by role, level, and location. Within each range, individual pay is based on factors such as job-related skills, experience, performance, and relevant education or training. 

In addition to the base salary, the successful candidate will also receive benefits and a generous equity package.

These ranges may be modified in the future to reflect evolving market conditions and organizational needs. While most offers will typically fall toward the starting point of the range, total compensation will depend on the candidate’s specific qualifications, expertise, and alignment with the role’s requirements.

Source: WHOOP careers (Ashby)

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