Remote Engineering Head at Jobgether

Winnipeg, Manitoba, Canada -

Full Time

Start Date

Immediate

Expiry Date

24 May, 26

Salary

0.0

Posted On

23 Feb, 26

Experience

5 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Engineering Leadership, Team Growth, Technical Roadmap Definition, Architectural Decisions, Engineering Standards, Code Quality, System Design, Incident Response, Delivery Management, Architecting for Scale, HSA/FSA Payment Infrastructure, API Development, Checkout Experiences, Cross-functional Engagement, Hands-on Coding, TypeScript

Industry

Internet Marketplace Platforms

Description

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Head Of Engineering - REMOTE. In this role, you will have a significant impact on shaping the future of healthcare payments technology. By leading a talented engineering team, you will establish best practices and ensure the development of reliable and cutting-edge systems. You will partner directly with founders, define engineering priorities, and create a culture of accountability. This position offers an opportunity to drive growth and execute architectural visions that align with the company's goals, influencing both the technical roadmap and team dynamics. \n Accountabilities Lead and grow the engineering team — recruit, mentor, and develop engineers across all levels, building a culture of craft, accountability, and velocity. Own the technical roadmap — partner with founders and product to define priorities, make architectural decisions, and ensure engineering investments align with company goals. Set engineering standards — establish best practices for code quality, system design, incident response, and on-call culture. Drive delivery — keep the team focused and unblocked, managing execution across sprints, projects, and longer-horizon initiatives. Architect for scale — lead the design of our HSA/FSA payment infrastructure, APIs, and checkout experiences to handle growing merchant and transaction volume. Engage cross-functionally — work closely with customers, sales, and operations to translate real-world needs into engineering priorities. Stay hands-on — roll up your sleeves when it counts; you're comfortable contributing directly to the codebase when needed. Requirements 8+ years of engineering experience, with at least 2–3 years in an engineering leadership role (EM, Staff/Principal, or Head of Eng). Proven team builder — you've hired, grown, and retained strong engineers, and you know what great engineering culture looks like. Strong technical foundation — you have depth in backend systems and APIs, and you're conversant across the full stack. Familiarity with TypeScript, Rust, Postgres, Redis, and AWS is a strong plus. Architectural thinker — you've designed and scaled distributed systems and know how to make the right tradeoffs between speed and rigor. Startup experience — you've worked at a seed-to-Series B company and understand what it means to build in a resource-constrained, fast-moving environment. Operator mindset — you bring structure and clarity without bureaucracy, and you know how to keep a small team moving fast. Benefits Define the engineering function at a company with a clear wedge in a $150B+ market. Work directly with founders on the highest-leverage technical and product decisions. Competitive salary with meaningful equity. Medical, dental, and vision plans. Unlimited PTO and sick days. Paid parental leave. Flexible, remote-first team with quarterly in-person meetups. \n Why Apply Through Jobgether? We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1

Responsibilities

The Head of Engineering will lead and grow the engineering team, establishing best practices, and owning the technical roadmap in partnership with founders and product. This role involves driving execution, setting engineering standards, and architecting scalable payment infrastructure.