Engineering Manager

Job Title: Engineering Manager

Location: Candidate must be located in Canada, preferably GTA region. Our office is located in Toronto, ON, Canada, but the role is remote/hybrid/flexible.

Reports To: Director of Engineering

We're looking for an experienced Engineering Manager to lead our Core and Growth teams; two foundational pillars of Practice Better's product organization. In this role, you'll guide the teams responsible for everything from booking, telehealth, and payments to onboarding, conversion, and early customer success. You'll play a critical role in shaping how we deliver reliable, high-impact experiences for our customers while building the systems and structure that support our next stage of scale.

This is a hands-on leadership role that blends strategy, execution, and mentorship. You'll partner closely with Product and Design to align on priorities, drive operational excellence, and ensure the right balance between innovation and stability. You'll also help evolve our development processes and foster a culture of ownership, curiosity, and continuous improvement across both teams.

If you're energized by leading talented engineers through growth, navigating complex systems and integrations, and finding scalable solutions that deliver real customer value - this role is for you.

What You'll Do

Team Leadership & Development

• Build, mentor, and empower two high-performing teams (Core Growth) responsible for product fundamentals and conversion-critical experiences.
• Hire top talent while maintaining high technical and cultural standards.
• Foster a culture of ownership, psychological safety, and continuous learning.
• Coach engineers and team leads toward technical excellence, autonomy, and strong cross-functional collaboration.
• Balance individual development with evolving business priorities.

Delivery & Execution

• Partner with Product and Design on roadmap definition, ensuring alignment between impact, effort, and strategic outcomes.
• Own prioritization across two teams, balancing short-term delivery, technical debt reduction, and platform scalability.
• Evolve our hybrid Kanban/Sprint structure—introducing just enough process to enable velocity and predictability without over-structuring.
• Continuously improve estimation, visibility, and delivery accountability across both teams.
  
  

Cross-Functional Collaboration

• Act as a key bridge between Engineering, Product, Design, and Customer Success.
• Collaborate with Platform and AI teams to support shared architecture and drive product innovation.
• Partner with the Technical Customer Support team to ensure operational alignment and rapid incident resolution.
• Translate complex technical updates into clear, actionable communication for business stakeholders.
  
  

Technical Oversight & Vendor Management

• Maintain oversight of 20 third-party integrations, ensuring reliability, uptime, and proactive vendor coordination.
• Make informed build-vs-buy decisions with consideration for cost, maintenance, and long-term scalability.
  Support vendor evaluation, contracts, and internal tooling adoption with technical and operational input.

Operational Excellence

• Own and evolve on-call, release, and incident management processes to ensure consistent service quality.
• Define and track operational metrics (deployment frequency, mean time to recovery, etc.) and team health indicators.
• Identify and remove systemic blockers to engineering productivity, driving continuous improvement.
  
  

AI & Innovation Leadership

• Partner with the AI team to embed agentic AI and automation into engineering workflows.
• Identify high-impact use cases for AI within the product and internal development processes.
• Stay current on emerging technologies, champion experimentation, and foster a mindset of innovation.
  
  

What You'll Bring

• Technical Depth Leadership Breadth - 8 years of software engineering experience, with at least 3 years in people leadership managing multiple teams or streams of work.
  
  
• Full-Stack or Backend Expertise - Strong technical grounding in web application architecture (React, , or similar), APIs, and integrations.
  
  
• Experience at Scale - Proven success balancing delivery speed and system reliability in a SaaS environment with significant product surface area.
  
  
• Integration & Vendor Savvy - Deep understanding of managing and maintaining complex third-party integrations (e.g. Stripe, Zoom, Fullscript) and vendor ecosystems.
  
  
• Operational Rigor - Hands-on experience improving incident response, CI/CD pipelines, and engineering processes to support sustainable growth.
  
  
• Collaborative Partner - Demonstrated ability to work cross-functionally with Product, Design, and Customer Success to deliver high-impact outcomes.
  
  
• Builder Mindset - Excited by ambiguity and energized by scaling systems, teams, and processes from 0→1 and 1→N.
  
  
• AI Curiosity - Awareness of current AI trends and enthusiasm for applying AI to improve development efficiency or customer experience.
  
  
• Values Alignment - A growth mindset, a bias for ownership, and a belief that better processes and tools help people deliver their best work.
  
  

Our Tech Stack

• .NET, AngularJS/jquery, Angular, and TypeScript
• [Mobile] Cordova, Java, Objective-C, and Swift
• MongoDB, S3, SQS, Lambda - AWS
• Bitbucket, Slack

Our Perks and Benefits:

• Unlimited Vacation: We believe you can be highly productive and still have plenty of time for life outside of work.
• Generous health benefits plan: Coverage starts from Day 1 and includes vision & dental.
• RRSP / 401K matching program for retirement savings.
• Home Office Allowance: $500/year to ensure your home office is set up for optimal comfort and productivity.
• Health & Wellness Allowance: $750/year to support your health & wellness-related goals and hobbies.
• Learning & Development Allowance: $1,000/year to explore a new skill, attend a conference, read some new books, etc.
• Sprout Family: Receive personalized support for the family-building process, accessing top-quality care. Schedule a consultation with Sprout's Team for guidance, education, coaching, and assistance in finding a top provider, addressing medical, legal, or regulatory concerns throughout your journey. Currently for Canadian Employees Only
• Inkblot: Access to one of Canada's leading digital mental health companies, focusing on offering secure online video counseling through our corporate mental health programs and individual counseling services. Currently for Canadian Employees Only
• Fully Remote: Work from the comfort of your own home with the choice to access our downtown Toronto office for a change of scenery.
• Events & Free Lunches: We prioritize weekly team bonding and monthly company-wide social events with a lunch stipend. We pride ourselves on maintaining a culture where everyone feels engaged, inspired, and excited to come to work every day.