Location: Calgary, Alberta

As one of the most significant purchases we'll ever make, a new home deserves to be the most exciting and enjoyable experience of our life. While owning a home should be simple and joyful, people's best asset is their least supported and biggest headache. Our clients mission is to help new homeowners to quickly and effortlessly begin enjoying their homes, and continue enjoying them. When ownership decisions can be complex and overwhelming, our client is the trusted unbiased guide to help make them faster.

They are hiring a Technical Delivery Lead working and reporting into the CTO to ensure delivery across the organization is an iron-clad.

WHAT YOU'LL BE DOING You'll be the operational backbone for our weekly release cadence; ensuring that Product, Engineering, Customer Experience, Finance, Data and Operations are aligned, informed, and ready to execute each week. This is an enablement and orchestration role, not people management. You'll prevent surprises, surface conflicts early, and make sure every department knows exactly what's shipping and what they need to do to support it.

Release Planning & Readiness

Own the pre-release checklist across all teams; confirming features are customer-ready, CX is trained on changes, Ops has operational adjustments queued, and Finance understands any billing/commercial implications

Run a weekly release planning session where Product confirms scope, Engineering commits to delivery, and you identify cross-departmental dependencies upfront

Surface conflicts and blockers early (e.g., this feature ships Thursday but CX needs 5 days lead time)

Create a single source of truth for each release; what's shipping, why, who needs to do what,



and by when Cross-Departmental Alignment

Cross-Departmental Alignment

Facilitate handoffs from Product > Engineering to ensure requirements are clear and testable before sprint begins

Bridge between Engineering and CX by translating feature scope into customer-facing readiness (documentation, training, FAQs, support runbooks)

Coordinate with Data on analytics readiness, new events/schemas needed, impact to existing reporting and tracking/measurement for feature success

Work with Ops to identify operational requirements early; infrastructure changes, monitoring needs, rollback procedures, incidents

Coordinate with Finance on commercial/billing impacts and ensure GTM alignment with the release

Drive alignment in ceremonies; standups, planning, demos, and cross-functional release syncs, ensuring decisions stick and action items have owners

Build credibility with strong-willed engineers and skeptical stakeholders through clarity, follow-through, and results. Your influence comes from trust and execution, not authority

Execution & Risk Management

Monitor sprint progress daily; flag at-risk work blocking the release or dependent teams

Run release ceremonies that drive clarity and accountability, not theater





Escalate trade-offs and scope decisions to Product Owner; help teams understand what changes when scope is at risk

Enforce testing and documentation standards as gates before release; ensure quality doesn't slip to meet the timeline

Post-release, gather feedback from all departments to improve the next week's process

WHAT YOU WILL NOT OWN

Technical decisions or code review (that's the development team)

Architecture or infrastructure decisions (that's the lead developer and Ops)

Mid-sprint scope decisions (the Product Owner decides)

People management, hiring, or performance reviews

Customer support or incident response (CX owns this; you ensure they're ready)

Must Have Skills

5+ years in a Product Manager, Program Manager, Technical Program Manager, or similar cross-functional role where you've worked closely with engineers and built trust across multiple disciplines

Proven experience at the intersection of Product, Engineering, and Operations - someone who's worn multiple hats

Track record of improving delivery speed without sacrificing quality for engineering teams shipping frequently

Comfort managing ambiguity and competing priorities in fast-paced environments

Natural facilitator. You get robust engineers and product thinkers to align without needing authority

Data-driven mindset: velocity, release health metrics, risk flagging, and continuous process improvement

Experience surfacing and escalating trade-offs. You're comfortable saying we can't do all three; which one drops?

Ability to build trust across departments through clarity, follow-through, and bias toward action

Comfort with Jira and modern software delivery practices

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📌 Technical Delivery Lead (Winnipeg)
🏢 GuruLink
📍 Winnipeg