• Lead, coach, and grow a team of platform engineers across Infrastructure, DevOps and Developer Experience. • Set technical direction for platform architecture and ensure roadmap execution • Balance short-term delivery with long-term investments in tooling, infrastructure, and reliability • Oversee cloud infrastructure, deployment pipelines, and operational tooling in a regulated environment • Design and build AI-powered internal tools and agentic workflows that automate tasks and augment engineering productivity • Improve developer productivity by reducing friction in onboarding, CI/CD, and local-to-prod workflows • Ensure systems are secure, scalable, observable, and resilient as Shakepay grows • Own incident management practices, postmortems, and sustainability of the on-call rotation • Collaborate closely with product engineering, security, and compliance stakeholders • Advocate for platform work by tying technical initiatives to business and customer impact

Role Description This role will be part of the team responsible for developing and deploying Data Engineering Platform and Integration Solutions. Primary responsibility will be to work closely with the Data Engineering team, Data Architects and AI Team to implement data solutions for the organization using Python, PySpark and other big data solutions, creating technical specification documents and test plans. Also provide support for the data solutions across the enterprise. Job Roles and Responsibilities - Understand business processes and how they are modeled in various systems. - Work with business users, technology teams, and executives to understand their data needs to create innovative solutions to fulfill them. - Design and implement data structures, workflows, and integrations between enterprise platforms to ensure the accurate and timely execution of business processes. - Maintain scalable data pipelines to support continuing increases in data volume and complexity. - Adhere to established best practices on data integration/engineering, as well as the future of our data infrastructure. - Manage and improve the performance of our database, queries, tools, and solutions. - Create and maintain data warehouse, data lakes, databases, tables, SQL queries, and ingestion pipelines, predictive models, and downstream analysis. - Write complex and efficient queries to transform raw data sources into easily accessible models for our teams and reporting platforms. - Prepare data for predictive and prescriptive modeling. - Identify and analyze data patterns. - Identify ways to improve data reliability, efficiency, and quality. - Work with analytics, data science, and wider engineering teams to help with automating data analysis and visualization needs, advise on transformation processes to populate data models, and explore ways to design and develop data infrastructure. - Collaborate, coordinate, and communicate across disciplines and departments. - Ensure compliance with HIPAA regulations and requirements. - Demonstrate Company’s Core Competencies and values held within. Qualifications - Minimum Graduation Degree and 12+ years’ related experience, three (3) of which should be inclusive of experience with schema designing, data modeling, designing, building, and maintaining data processing systems. Bachelor’s degree in computer science, information technology or a similarly relevant field is highly preferred. - Experience with advanced analytics tools for Object-Oriented/object function scripting using languages such as Python and PySpark. - Database development experience using ETL Process, SQL, SPARK, or BigQuery and experience with Delta Lakes and Data Warehouse, use of Databricks or Snowflakes or similar products. - Experience in triaging data issues, analyzing end-to-end data pipelines and working with business users in resolving issues. - Experience in working with data governance/data quality and data security teams and specifically data stewards and security officers in moving data pipelines into production with appropriate data quality, governance and security standards and certification. - Exposure to Big Data Development using various tools & techniques Databricks, Snowflakes, OCI, Hive, Impala, Spark, etc. - Exposure to machine learning, data science, computer vision, artificial intelligence, statistics, and/or applied mathematics. - Exposure to agile methodologies and capable of applying DevOps and increasingly DataOps principles to data pipelines. - Excellent communication skills (verbal, listening and writing). - Ability to build and manage data pipelines for data structures encompassing data transformation, data models, schemas, metadata and workload management. - Ability to work with both IT and business in integrating analytics and data science output into business processes and workflows. - An agile learner who brings strong problem-solving skills and enjoys working as part of a technical, cross-functional team to solve complex data problems. - Able to prioritize and manage multiple projects and requests at any one time. - Strong attention to detail when identifying data relationships, trends, and anomalies. - Thinking through long-term impacts of key design decisions and handling failure scenarios. - Ability to effectively share technical information, communicate technical issues and solutions to all levels of business. - Ability to meet strict deadlines, work on multiple tasks and work well under pressure. Requirements - The salary range for this position is $130-140K. Specific offers take into account a candidate’s education, experience and skills, as well as the candidate’s work location and internal equity. This position is also eligible for health insurance, 401k and bonus opportunity. Benefits - Medical, dental and vision coverage with low deductible & copay. - Life insurance. - Short and long-term disability. - Paid Parental Leave. - 401(k) + match. - Employee Stock Purchase Plan. - Generous Paid Time Off – accrued based on years of service. - 10 paid company holidays. - Tuition reimbursement. - Flexible Spending Account. - Employee Assistance Program. - Sick time benefits – for eligible employees, one hour of sick time for every 30 hours worked, up to a maximum accrual of 40 hours per calendar year, unless the laws of the state in which the employee is located provide for more generous sick time benefits. EEO Statement Claritev is an Equal Opportunity Employer and complies with all applicable laws and regulations. Qualified applicants will receive consideration for employment without regard to age, race, color, religion, gender, sexual orientation, gender identity, national origin, disability or protected veteran status. Application Deadline We will generally accept applications for at least 5 calendar days from the posting date or as long as the job remains posted.

• Lead and manage a diverse, remote-first, agile team supporting iterative and incremental shipping. • Steer the team's technical direction through hands-on contributions and conducting rigorous technical due diligence on proposals, tooling evaluations, and architectural decisions. • Evolve how the team works by putting AI at the center of execution, and to ensure platform primitives are built for seamless consumption by agents as well as human builders. • Leverage quantitative and qualitative metrics (DORA/SPACE) to eliminate bottlenecks and make data-informed decisions. • Ensure that the team is staffed for success. • Facilitate the growth and development of the individuals on your team. • Communicate regularly with stakeholders, providing updates on progress, challenges, and solutions. • Collaborate with cross-functional peers such as in Product, Design to set goals and define objectives,

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further. Over 70,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, GV, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. 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 (~120) 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 & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js - Datastores: Postgres, Redis - Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka - Monitoring: Datadog, PagerDuty, Sentry - Version Control: Github, PagerDuty - Vulnerability Management: Snyk, Semgrep - Cloud Security: Lacework About this role At Headway, we’re building a national network of therapists who accept insurance — and making mental healthcare radically more accessible in the process. Supporting providers isn’t just about connecting them with patients — it’s about delivering the tools they need to manage their practice with ease, confidence, and compliance. Our providers are the heart of Headway’s mission — and empowering them with an easy-to-use platform is critical to both their success and the quality of care patients receive. Whether it’s saving providers time, simplifying documentation, or ensuring compliance, this role is at the center of our providers’ lives. As an engineering leader at Headway, you will be responsible for leading and growing the engineering pods behind our core provider experiences through people development, strategic planning, and hands-on technical support or guidance. You get to play a leading role in defining what and how these teams build, setting up how the teams operate, support, and ultimately drive best-in-class user experiences that have a measurable impact on our ability to execute and meet the demands of a high growth startup. This is a critical leadership role for Headway and our mission to make mental healthcare more accessible. By helping providers spend less time on administrative tasks and more time on care, you’ll directly support both provider satisfaction and patient access. 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 a Senior Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Design 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 managed engineering teams of 12+ engineers - Lead and managed multiple pods, as well as other engineering managers - 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 120 to 175+ through the remainder of the year Below are additional experiences we think help engineering managers succeed at Headway: - You have 5-7+ years of experience as an experienced Engineering Manager, concurrently leading multiple teams, and/or managing managers - You have 3-5+ years of experience as a Software Engineer - 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 a strong technical foundation that allows you to ensure your team is making appropriate technical decisions - You have a track record of building and leading high performing teams that have effectively delivered business outcomes through technical investments - You have a track record of working well across teams and functions - It's a nice to have if you've had prior experience with Python and React and working with AWS infrastructure - It's a nice to have if you've had experience in health tech, building user-facing products - 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 team and people leadership experiences and complete one technical (systems design) interview. - Final rounds: You’ll meet team members across product and engineering leadership for 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: 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. 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 #LI-AC1 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.