Job Overview
Location
Indiana, USA
Job Type
Full-time
Category
Engineering Manager
Date Posted
February 22, 2026
Full Job Description
đź“‹ Description
- • As the Head of Engineering at Withflex, you will be at the forefront of defining and executing the technical vision for a company poised to revolutionize healthcare payments. This is a pivotal leadership role where you will not only guide the engineering team but also directly influence the strategic direction of the company, partnering closely with the founders to shape our technological future. You will be instrumental in scaling our platform to meet the demands of a rapidly growing market, ensuring reliability, performance, and innovation.
- • Your primary responsibility will be to lead and cultivate a high-performing engineering team. This involves attracting top talent, fostering a culture of continuous learning and development, and mentoring engineers at all levels. You will be responsible for building a team that embodies craft, accountability, and velocity, ensuring that we not only meet but exceed our ambitious goals.
- • You will own the technical roadmap, collaborating with the founders and product management to translate business objectives into actionable engineering priorities. This includes making critical architectural decisions, evaluating new technologies, and ensuring that our engineering investments are strategically aligned with the company's long-term vision and growth trajectory.
- • Establishing and upholding rigorous engineering standards will be a key aspect of your role. You will define best practices for code quality, system design, robust incident response, and a healthy on-call culture. This commitment to excellence will ensure the stability and scalability of our platform as we expand.
- • Driving efficient and effective delivery is paramount. You will empower the engineering team to focus and overcome obstacles, managing execution across sprints, complex projects, and longer-term strategic initiatives. Your leadership will ensure that we consistently deliver high-quality software on time and within scope.
- • A significant part of your mandate will be to architect for scale. You will lead the design and implementation of our core HSA/FSA payment infrastructure, APIs, and checkout experiences, ensuring they are robust enough to handle increasing merchant and transaction volumes. This requires a forward-thinking approach to system design, anticipating future needs and building for resilience.
- • You will serve as a crucial cross-functional liaison, working closely with customers, sales, and operations teams. This engagement will provide invaluable insights into real-world needs and market dynamics, allowing you to translate these requirements into concrete engineering priorities and product enhancements.
- • While leading the team, you are also expected to remain hands-on. You will be comfortable contributing directly to the codebase when necessary, demonstrating technical leadership by example and diving into complex problems to help the team find solutions. This blend of strategic leadership and practical execution is vital for a fast-paced startup environment.
- • You will play a key role in shaping the company's technical culture, fostering an environment that encourages innovation, collaboration, and a shared sense of ownership. Your leadership will be critical in navigating the challenges and opportunities of a rapidly evolving FinTech and HealthTech landscape.
- • This role offers a unique opportunity to define the engineering function from its foundational stages within a company that has identified a significant market opportunity. You will be empowered to make impactful decisions and build the systems that will power the future of healthcare payments.
🎯 Requirements
- • 8+ years of progressive engineering experience, with a minimum of 2-3 years in a formal engineering leadership capacity (e.g., Engineering Manager, Staff/Principal Engineer, or Head of Engineering).
- • Proven track record of building, growing, and retaining high-performing engineering teams, coupled with a deep understanding of what constitutes an excellent engineering culture.
- • Strong technical acumen with significant depth in backend systems and API design, and a broad understanding of full-stack development principles.
- • Experience architecting and scaling distributed systems, with a demonstrated ability to make informed trade-offs between development speed and technical rigor.
- • Prior experience working in a startup environment, ideally from seed to Series B, with a clear understanding of the dynamics and resource constraints of fast-moving companies.
🏖️ Benefits
- • Competitive salary and meaningful equity in a high-growth startup.
- • Comprehensive medical, dental, and vision insurance plans.
- • Unlimited Paid Time Off (PTO) and sick days to support work-life balance.
- • Generous paid parental leave policy.
- • Flexible, remote-first work environment with opportunities for in-person team meetups.
Skills & Technologies
TypeScript
Rust
PostgreSQL
Redis
AWS
Remote
About Withflex Inc.
Withflex is a technology company focused on revolutionizing the way businesses manage their flexible workforce. Their platform provides a comprehensive solution for hiring, onboarding, managing, and paying contingent workers, freelancers, and contractors. By centralizing these processes, Withflex aims to streamline operations, ensure compliance, and reduce administrative overhead for companies. They cater to businesses of all sizes looking to leverage flexible talent efficiently and effectively, offering tools for talent sourcing, contract management, time tracking, and automated payments. Withflex operates within the HR tech and gig economy enablement sectors.
