Engineering Manager

Department: R&D

Location: Toronto, Canada

Employment Type: FullTime

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

OpenLoop is looking for an Engineering Manager to join our team. The ideal candidate will have a strong technical background, proven leadership experience, and a passion for building high-quality software products that deliver exceptional user experiences. The role will begin as fully remote, with the potential to transition to a hybrid work model in the future.

Responsibilities:

• Build & Lead the Toronto Engineering Hub

  • Establish and grow our Toronto engineering presence

  • Hire, mentor, and develop a high-performing team of engineers

  • Set team culture, operating cadence, and engineering standards from the ground up

  • Partner with leadership on hiring plans, team structure, and long-term growth

  Product Engineering Execution

  • Work closely with product and business stakeholders to deliver high-impact solutions in fast-moving, ambiguous environments

  • Translate evolving requirements into clear technical direction and execution plans

  • Drive rapid iteration cycles and enable teams to ship quickly while maintaining quality

  Technical Leadership, Execution & Cross-Functional Delivery

  • Guide architectural decisions and ensure systems are scalable, secure, and maintainable

  • Provide hands-on technical leadership when needed, especially in early stages

  • Drive delivery of high-quality software across multiple initiatives in fast-moving environments

  • Partner closely with Product, Design, and business stakeholders to align on priorities and outcomes

  • Communicate progress, risks, and tradeoffs clearly to both technical and non-technical audiences

  • Contribute to product direction through technical insight and customer context

  • Establish lightweight processes that enable speed, ownership, and accountability

  • Identify and remove blockers to keep teams moving efficiently

  • Foster a culture of ownership, learning, and continuous improvement

• Other duties as assigned.

Requirements

• 8+ years in software engineering, including 2–4+ years managing engineers

• Experience leading high-performing teams and delivering complex projects

• Solid understanding of modern software architecture and system design

• Experience working with cloud environments (AWS preferred)

• Familiarity with SDLC, CI/CD, and agile practices

• Strong communication and stakeholder management skills

• Ability to translate business goals into technical execution

• Experience with hiring, coaching, and retaining engineers

Rippling EOR partners with Sterling Capital Brokers to offer Canadian employees extended health plans.

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.