Head of Engineering (Insurance)

There is a lot that we're building at Headway, but ensuring that our underlying systems behind our insurance platform reliably power patient, provider, and payer (insurance customer) experiences is mission critical in our efforts to make mental healthcare more accessible and affordable for everyone. As Head of Engineering for the Insurance Group, you will inherit a strong, growing set of engineering pods that deliver critical systems behind benefits and eligibility services, claims, billing infrastructure, payments, and customer support tooling. Your mandate will be to guide and scale this group as Headway grows, ensuring it continues to deliver reliable, secure, and high-impact technology at scale.

Reporting to Headway’s CTO, you’ll be a senior leader within our rapidly growing Engineering Org, responsible for strategic planning, organizational design, and talent development. You’ill set the technical vision and operating model for the group, ensuring our systems evolve to meet the complexity and growth of our marketplace. You’ll be responsible for enabling experiments, accelerating development velocity, and scaling infrastructure that supports one of the most important dimensions of our business: making insurance work seamlessly for providers, patients, and payers.

Your teams will be highly cross-functional, partnering closely with other engineering, product, design, data, customer success, growth, clinical, and other functions to understand the needs of our insurance partners and deliver solutions that redefine how mental healthcare integrates with the broader healthcare ecosystem.

We’re looking for a platform-minded engineering executive who is relationship-obsessed, drives results, and enables teams to deliver with technical excellence. This is an exciting opportunity for a mission-aligned leader to scale one of the most critical engineering groups at Headway and make an immediate impact on the way we expand mental healthcare access.

• Build the vision and roadmap for the next chapter of our Insurance Engineering group, driving company-level objectives and powering best-in-class provider, patient, and payer experiences
• Contribute to the broader 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 ensure alignment on strategic goals and execution against highly impactful OKRs and KPIs
• Lead and scale multiple engineering pods, ensuring process, architectural, and product alignment across the group
• Develop and grow your managers and team of teams through mentorship, feedback, and career development frameworks
• Recruit and build diverse, high-performing engineering teams that thrive on collaboration and technical excellence
• Shape engineering culture, process, and operating norms as Headway grows from 110 to 150+ engineers in the coming year

• You have 8+ years of experience as an engineering leader, including managing managers, with a track record of building and scaling high-performing organizations that deliver business impact through technical innovation
• You have previous experience as a Software Engineer, and a strong technical foundation that allows you to guide and challenge technical decisions
• You are able to see things at a 300-ft view, while also diving deep into highly technical challenges that affect scale, reliability, and user experience
• You have a strong product mindset, having built cross-functional relationships that build trust and enable great user experiences
• You have a passion for building resilient, scalable platforms that unlock growth in new product areas
• It’s a nice to have if you’ve had experience in health tech or with complex platform domains such as insurance, payments, or billing
• BS, MS in Computer Science or related field

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First rounds: You'll meet with an engineering leader on the team to go deeper into your technical and people leadership experiences
• Final rounds: You’ll meet several more team members for one technical and multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

• Salary information is based on a single salary target per role, and the starting salary for a Head of Engineering starts at $275,000 and can increase to $380,000 based on industry tenure and experience.
• Benefits offered include:
  • 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 as well as a Holiday Break during the week between December 25th and December 31st
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development

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