Associate Client Delivery Lead

About us

We are a technology consulting firm providing high-impact data and automation solutions in healthcare, fintech, and insurance. Our clients range from startups to well-established enterprises. Our mission is to help our clients create outsized value by being the highest-performing technology partner they've ever worked with. You will join a team of over 40 members distributed across Canada, working in a remote-first environment. Our clients choose us because we practice extreme ownership and deliver solutions that truly work. We move quickly, think deeply, and take pride in our partnerships.

The Associate Client Delivery Lead runs delivery on projects once they are scoped and shaped, picking them up and owning them week to week until they are live and delivered. Your Client Delivery Lead stays accountable for the client relationship and the commercial scope; you own whether the thing actually ships. You will be paired with one Client Delivery Lead and their pod, running two to four concurrent workstreams at steady state. This is a delivery seat, not a coordination seat; you will be in front of client stakeholders, directors and VPs at large enterprises.

• Own project outcomes and client satisfaction by guiding the team to deliver solutions that generate clear business value.
• Develop a deep understanding of the client’s business and industry to solve problems effectively.
• Communicate efficiently with the client throughout delivery, proactively addressing concerns, maintaining alignment, and becoming their trusted advisor.
• Translate business objectives into actionable technical requirements, ensuring teams focus on the right problems.
• Develop and maintain delivery roadmaps, defining scope, milestones, timelines, and success criteria.
• Lead cross-functional collaboration by aligning technical, product, and business stakeholders around a shared vision and delivery approach.
• Identify risks, assumptions, and blockers early, driving clarity and making informed recommendations to keep delivery on track.
• Apply critical thinking to challenge assumptions, ensuring we solve the right problem and deliver solutions that create meaningful impact.

• 4–7 years of experience in roles that combine business acumen with hands-on Automation and AI delivery (e.g., consulting, product, startup, or delivery-focused environments).
• Deep, daily use of AI tooling (Claude, ChatGPT, or equivalent); you're noticeably faster than your peers because of how you work, and can explain how.
• Experience leading cross-functional delivery (e.g., product, data, engineering, design) where outcomes, not activity, were the measure of success.
• Skilled at working in ambiguity and being able to break down complex problems into well-defined solutions independently.
• Strong product-first mindset to analyze complex problem spaces and understand customer landscapes to inform solutioning.
• Effective stakeholder management skills, including guiding conversations, communicating trade-offs
• Exceptional documentation and communication skills that enable both internal and client teams to act with clarity and confidence.
• Strong interpersonal skills and proven ability to build trusted client relationships.
• At least one project you took to go-live and hypercare/support where your name was on the outcome.
• Comfortable being the one who reads the contract and knows what's in scope.

• Familiarity with the insurance, fintech, or healthcare industries is preferred.
• You've been through a Privacy Impact Assessment or a security architecture review and can describe how it went sideways.
• You've worked with an external vendor from the client side.
• Enough technical literacy to follow a technical design document and ask a useful question; you don't need to write code.
• You've built something yourself with AI tooling, even a personal workflow.

• Flexible hours: We are a fully remote company. Work on your schedule (pick up the kids, go to the dentist), you decide when you work.
• Compensation: We offer a competitive salary and health benefits package, including a Wellness spending account.
• Continuous learning: Access a dedicated learning budget to deepen your expertise.
• Time off: Flexible paid vacation days and sick days.
• Annual team retreat: Once a year, we meet in person to collaborate, reconnect, and reset.