Director of Engineering - Booking Group

About The Role

Booking is one of the most critical parts of Jane's platform. Scheduling is at the heart of how clinics operate, helping practitioners stay on time, reduce administrative work, and deliver a great patient experience. It's also one of Jane's highest-scale systems, handling more than 70% of all API traffic. The group owns Scheduling, Patient Booking, Mobile, Communications, Telehealth, and Marketplace. Earlier this year, we celebrated 500 million arrived appointments with Jane and 250,000+ practitioners interact with Jane on a daily basis.

You'll lead across five teams with the opportunity to evolve one of Jane's most business-critical product areas. This is a leadership role focused on building exceptional engineering teams, growing engineering leaders, and creating the environment for teams to do their best work. You'll help shape the technical direction, organization, and ways of working as the group continues to innovate and provide best in class experiences to our customers.

AI will be central to that journey. We're looking for someone who understands how agentic workflows and AI-assisted development are changing how software is built and is excited to help define what great engineering looks like in an AI-native world. If you're a builder who enjoys growing organizations, developing leaders, and shaping both the technical and AI direction of a high-scale platform, we'd love to meet you.

What Impact We’re Looking for You to Make

• Lead our Booking engineering org to ship at high velocity without sacrificing quality, even as the group expands into new product lines and rising customer demand.

• Drive faster, smarter building across Booking by embedding a clear point of view on AI into workflows and team structure, without compromising quality.

• Build incredible experiences for patients and clinics, in tight partnership with Product, Design, and the wider business across Booking's trio model.

• Grow your team of strong engineering leaders and builders, coaching your teams, investing in their skills, while raising the bar for engineering excellence and customer delight in step with Jane's values.

• Shape Booking's technical roadmap to track Jane's growth initiatives, partnering with stakeholders across the business as new product lines and customer demand take the company in new directions.

What Experience We Need

• Track record of 7+ years leading engineering teams, including managing managers, staying close to the technical problems your team faces and building alongside them - not several years removed from the work - and driving team growth and results by unlocking a team's potential.

• Experience leading engineering teams building products that customers rely on every day, standing up to real-world, on-demand traffic from large numbers of users, with a strong customer UX bar.

• Experience as an active builder who leads by example on AI - you may have built your own tools or workflows - with a developed, specific point of view on AI's impact on software delivery within an existing platform, including fluency with concepts like evals and the forward deployed engineer model.

• Experience translating technical work into terms product and business stakeholders act on, managing dependencies across groups and advocating clearly for customer needs.

• Experience leading with an iterative, experimentation-first approach to building - shipping, learning fast, and adjusting course. Some experience in a highly regulated area such as healthcare or fintech is a plus.

• Experience scaling engineering teams through periods of real growth - new product lines, rising customer demand, increasing scale - rather than just steady-state maintenance.

More About Jane

Jane is a founder-led, high-growth SaaS company with a remote-first team working across Canada, the US, and the UK, united by our mission to help the helpers. This role is remote first. We are not hybrid.

We build the products and tools that thousands of clinics rely on every day to run their businesses, care for their patients, and grow their communities. That level of impact means every person at Jane plays an important role in how we show up for our customers. We're all responsible for being deeply connected to their needs, obsessed with improving their experience, and proud of the difference our work makes in their day-to-day lives.

Jane is growing fast, and that growth brings exciting challenges that call for adaptability, resilience, learning agility, and humility. We're proud of what we've built and quick to admit what we don't know yet. We listen, learn, and adjust as we go. More than 70,000 businesses run on Jane which has 250,000+ practitioners interacting with our product on a daily basis and growth is continuing to accelerate.

Our goal isn't just delivery - it's delight. We move quickly, communicate openly, and solve real problems together. If you're energized by ambiguity, motivated by impact, and eager to learn with others, you'll thrive at Jane.

Compensation & Benefits

At Jane, we're committed to paying fairly, clearly, and above all, paying for growth. We're open to candidates in Canada or the US for this role, and pay according to the band for wherever you're based: CAD $228,000 to $370,500 in Canada, or USD $240,000 to $390,000 in the US. These are large ranges by design - they reflect the full growth journey someone might take in the role, from developing skills early on to achieving excellence.

Most new hires join at the accomplished stage - CAD $270,800 or USD $285,000 depending on location. A starting salary below this typically reflects strong potential still developing key skills; salaries above it usually apply to existing team members with significant impact and deep Jane-specific knowledge. We believe in paying for growth - you'll have regular career development conversations with your manager, and your compensation will grow as you gain experience and contribute meaningfully to our mission.

This role also includes equity through our JSOP (Jane Stock Option Plan). Our stock has grown 11x over the past six years, with three opportunities to exercise options along the way. Jane was valued at $1.8B in May 2025, and with the backing of TCV, we have ambitious plans ahead.

You can explore our benefits package here: Canadian Benefits · US Benefits