Headway - Staff Software Engineer (Payer)
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Requirements
• We’re looking for experienced engineers who have the ability to deal with ambiguity and learn new technologies and systems. Below are some additional experiences we think help engineers succeed at Headway. • For all engineers: • For all engineers: • You have experience working across the stack on modern web applications • Strong understanding of at least one programming language and comfortability with others • Shaped work to achieve company and team goals • Flexed into new technical and non-technical areas as projects require • Committed team member supporting the growth of those around them • For staff engineers: • Has designed and scaled ML / LLM-powered systems in production • ML / LLM-powered systems in production • Architected complex systems spanning multiple technical domains or product areas (e.g., publishing npm packages or owning infrastructure depended on by multiple teams) • Driven technical vision and strategy at the organization level, by writing and reviewing technical design documents and participating in quarterly planning activities • Established engineering standards and best practices across multiple teams • Led major technical initiatives requiring coordination across multiple teams • Mentored senior engineers and technical leaders • Our interview process • 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. • Initial screen • First round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team. • First round • Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway. • Final rounds • 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! • References and the Offer
Responsibilities
• Sets the Technical Standard: You make technical decisions that optimize for maintainability and scale, not just shipping speed. You proactively improve your team's engineering velocity - whether that's refining tooling, improving automation, or establishing patterns that prevent entire categories of bugs. • Sets the Technical Standard: • Mentor by Default: You pull engineers into design discussions without being asked. Your code reviews teach, not just gatekeep. You make sure knowledge gets shared across the team, not siloed in one person's head. • Mentor by Default: • Ships Fast, Iterates Faster: You can move from problem statement to working solution quickly. You'd rather ship a good v1 this week than a perfect v1 next month. Real feedback from therapists and patients is worth more than another round of design review. • Ships Fast, Iterates Faster: • Quick Study in Complex Domains: Healthcare is a maze of payers, regulations, and exceptions. You don't need prior healthcare experience, but you need to be someone who dives into unfamiliar domains and builds a working mental model fast. • Quick Study in Complex Domains: • Motivated by Impact: You want your engineering skills applied to problems that matter. Mental healthcare access is broken in America, and you want to be part of fixing it. • Motivated by Impact: • Communicates with Precision: Whether it's a Slack thread, a design doc, or a cross-team meeting, you communicate clearly and concisely. You know that great engineering is wasted if you can't bring people along. • Communicates with Precision: • AI Frontier Tinkerer: You don't just use AI tools - you push their limits. You've experimented with applying LLMs to real workflows, whether that's code generation, operational automation, or developer tooling. You bring a builder's mindset: what can we automate, what should stay human, and how do we ship it responsibly in healthcare? • AI Frontier Tinkerer: • Our Interview Process • 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. • Initial screen • First round: You'll do a live coding interview with Karat, our technical interviewing partner. It's a great opportunity to showcase your problem-solving skills and learn more about what our engineering team is building. • First round: • Final rounds: You’ll meet several team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway. • Final rounds • 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! • References and the Offer
Benefits
• The expected base pay range for this position is $224,000 - $280,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level. • We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential. • Equity Compensation • Medical, Dental, and Vision coverage • 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 • Employee Assistance Program (EAP) • Training and professional development • We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. • Headway participates in E-Verify. To learn more, click here. • A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.
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