Director of Engineering (Developer Productivity, Enablement & Infra Tooling)

About Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small (~85) but mighty team using technology to build that future (and have a fun time while doing it!).

Principles that guide us:

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they’re facing. 
• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

• Languages: Python 3, TypeScript
• Libraries: FastAPI, SQLAlchemy, React
• Datastores: Postgres, Redis, DynamoDB
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark, Flink, and Kafka
• Monitoring: Datadog, PagerDuty
• Version control: Github

About this role

There is a lot that we're building at Headway, but there are a few teams we’re building where your engineering leadership could make a measurable impact, including our DevEx (Developer Experience / Developer Tooling) and Infra Tooling (Core Infrastructure) teams - owning everything related to the Developer Productivity, and infrastructure, architecture, and scalability of Headway’s platform. You and your teams will be responsible for the whole Developer experience and core infra product lifecycle - from setting the vision to driving execution and measuring impact. You'll have the opportunity work closely with the rest of Headway engineering to understand the needs of our internal teams, while bringing in industry wide best practices and latest tools to up-level our engineering teams.

As an engineering leader at Headway, you will be responsible for establishing and growing these tech teams through hiring, people development, strategic planning, and potentially hands-on technical support or guidance. You get to play a leading role in setting up how the teams operate, defining what and how they build, and ultimately drive best-in-class internal user experiences that have a measurable impact on our ability to execute and meet the demands of a high growth startup. 

Who you are

We’re looking for experienced engineering team leaders and people managers who are relationship-obsessed, drive results and enable their teams to build for technical excellence. As an Engineering leader at Headway, you will work closely with other Engineering leaders, Product, Design, Operations and Business teams to help shape the future of the engineering organization. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact on our rapidly scaling engineering team.

• Lead and manage multiple teams of 4-6+ engineers
• Ensure there is process and product alignment across your team
• Develop and grow your team through weekly 1-1s, mentorship, and feedback
• Work with and help develop aspiring engineering leaders within the engineering team
• Contribute to the broader company strategy and product roadmap
• Help build out our engineering team as the headcount grows from 80 to 120+ through the remainder of the year

Below are additional experiences we think help engineering managers succeed at Headway:

• You have 5+ years of experience as an Engineering Manager, leading teams of software engineers focused on developer productivity and developer enablement
• You have 3-5+ years of experience as an DevEx, Infrastructure or Software Engineer
• You are passionate about building infrastructure and developer experience / developer tooling as a Product
• You have a track record of building and leading high performing teams that have effectively delivered business outcomes through technical investments
• You have a strong technical foundation that allows you to ensure your team is making appropriate technical decisions
• You have have a track record of working well across teams and functions
• You have a strong product mindset and have built strong cross-functional relationships that drive optimal user experiences and build trust with users
• You have experience working with AWS infrastructure 
• It's a nice to have if you've had prior experience with Python
• BS, MS in Computer Science or related field

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. 
• 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!

Compensation and Benefits:

• Salary information is based on a single salary target per role, and the starting salary for an experienced Engineering Manager is $238,000 and can increase to $270,000 based on industry tenure and experience (Director-level).
• 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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