Headway

Head of Engineering, Platform

Headway

full-time

Posted on:

Location Type: Remote

Location: Remote • California, New York, Washington • 🇺🇸 United States

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Salary

💰 $275,000 - $380,000 per year

Job Level

Lead

About the role

  • Build the vision and roadmap for the Insurance Engineering group, driving company-level objectives and powering provider, patient, and payer experiences
  • Contribute to company strategy and technical roadmap as a member of the engineering leadership team
  • Partner with senior leaders across product, business, data, design, clinical, legal, and compliance to align on strategic goals and OKRs/KPIs
  • Lead and scale multiple engineering pods delivering benefits/eligibility, claims, billing, payments, and customer support tooling
  • Ensure systems are reliable, secure, and scalable to meet marketplace complexity and growth
  • Enable experiments, accelerate development velocity, and scale infrastructure supporting critical business dimensions
  • Recruit, develop, and mentor managers and teams; shape engineering culture, process, and operating norms
  • Report to the CTO and drive strategic planning, organizational design, and talent development

Requirements

  • 8+ years of experience as an engineering leader, including managing managers
  • Previous experience as a Software Engineer
  • Strong technical foundation to guide and challenge technical decisions
  • Ability to see things at a 300-ft view while diving deep into technical challenges affecting scale, reliability, and user experience
  • Strong product mindset with experience building cross-functional relationships
  • Passion for building resilient, scalable platforms that unlock growth
  • Experience recruiting and building diverse, high-performing engineering teams
  • Experience developing and growing managers through mentorship and career frameworks
  • Nice to have: experience in health tech or with complex platform domains such as insurance, payments, or billing
  • BS or MS in Computer Science or related field
Benefits
  • Equity Compensation
  • Medical, Dental, and Vision coverage
  • HSA / FSA
  • 401K
  • Work-from-Home Stipend
  • Therapy Reimbursement
  • 16-week parental leave for eligible employees
  • Carrot Fertility annual reimbursement and membership
  • 13 paid holidays each year and Holiday Break during the week between December 25th and December 31st
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development

ATS Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
software engineeringtechnical roadmap developmentscalable platform developmentsystem reliabilityuser experience optimizationengineering managementcross-functional collaborationmentorshiporganizational designstrategic planning
Soft skills
leadershipcommunicationstrategic thinkingteam buildingproblem-solvingrelationship buildingcultural shapingtalent developmentadaptabilityvisionary thinking
Certifications
BS in Computer ScienceMS in Computer Science
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