AI Technical Program Manager in Winnipeg

3Pillar Global builds breakthrough software products that power digital businesses. We partner with the world's leading organizations to design, build, and scale software solutions — combining human expertise with AI-driven delivery to achieve outcomes that matter. As a Technical Program Manager, you will be the operational backbone of our most strategic client engagements. Reporting to a Product Delivery Director, you will translate executive-level vision into structured, accountable program execution — owning the full delivery lifecycle from pre-SOW solutioning through to successful client outcomes. This is not a coordination role. You will be a technical leader, a trusted delivery lead, and a practitioner who understands how modern AI-driven delivery teams operate and where human judgment is irreplaceable.

Key Responsibilities:

• Lead engagements where AI agents are embedded across the SDLC — from requirements gathering and code generation to testing, documentation, and release management.
• Understand where AI drives genuine efficiency gains and where human-in-the-loop oversight is required to maintain quality, compliance, and client trust.
• Contribute to the ongoing evolution of 3Pillar's AI-driven delivery practices, bringing lessons learned from the field back into our operating model.
• Partner with the Solutioning team to define engagement scope, approach, and solution architecture prior to contract execution.
• Contribute to SOW development — translating client requirements into structured delivery commitments with clear assumptions, risks, and effort estimates.
• Bring a point of view on how AI-driven delivery can accelerate outcomes and where it introduces risk that must be managed.
• Serve as the primary day-to-day delivery lead for technical and mid-management stakeholders, building trust through consistent delivery and clear communication.
• Facilitate executive-level program governance in support of the Product Delivery Director, ensuring alignment on objectives, risks, and progress.
• Proactively surface issues, manage escalations, and maintain client confidence through transparency — especially on fixed-outcome engagements where contractual accountability is high.
• Own end-to-end program execution across 2–3 concurrent client accounts with typical annual contract values in the $1–2M range, or a single large strategic engagement, depending on scope.
• Own the quality bar for everything the engagement ships — accountable for defining what 'done' means, enforcing it, and standing behind the result with the client.
• Anticipate delivery bottlenecks, manage cross-functional dependencies, and drive issue resolution without waiting to be asked.
• Build and maintain delivery mechanisms — cadences, dashboards, escalation paths, and reporting structures — that provide clarity to all stakeholders.
• Establish and maintain the human oversight model for AI-generated work: review depth, test coverage expectations, security and compliance checks, and clear sign-off ownership at each stage of the SDLC.
• Maintain the contractual thread from SOW through execution, ensuring commitments, assumptions, and dependencies stay visible to both sides and that delivery reality is reconciled against what was sold.
• Propose and make tradeoffs and communicate them clearly.

Minimum Qualifications:

• Engineering Foundation. Career trajectory: you started in software engineering or a closely related technical discipline and grown into process and program leadership.
• 10+ Years of Experience: spanning software engineering, technical leadership, and program management — with at least 5 years in a program or delivery leadership role on client-facing or product-facing engagements.
• Demonstrated Experience Deploying AI Agents into Delivery Workflows — not just using AI tools, but integrating agents into the SDLC and managing the human oversight model that keeps them productive and accountable.
• Clear Understanding of Where AI Drives Efficiency Across the SDLC: and where human judgment, accountability, and oversight are non-negotiable.
• Experience on Fixed-Outcome or SOW-Based Engagements: where you owned contractual delivery commitments, not just best-effort project management.
• Proven Ability to Manage External Client Relationships: at the technical and mid-management level — building trust through delivery, not just relationship management.
• Experience Contributing to Pre-Sales or Pre-SOW Solutioning: scoping engagements, estimating effort, and shaping delivery approaches before contracts are signed.
• Cloud Platform Fluency: Working fluency in at least one major cloud platform — AWS, Azure, or GCP — sufficient to engage credibly on architecture decisions, infrastructure tradeoffs, and cloud-native delivery patterns.
• Professional Services Context. Experience delivering in a consulting, agency, or services environment, or as an internal consultant to executive stakeholders — you understand the difference between building a product and delivering an outcome someone bought.
• Excellent English language skills, both verbal and written.

Additional Experience Desired:

• Experience running multiple concurrent accounts rather than a single engagement.
• A track record of bringing field lessons back into an operating model — playbooks, standards, or practices that outlived the engagement that produced them.
• Experience using quantitative and qualitative data to inform design decisions and drive change.

While we work nearly 100% remote, occasional travel (~2-3x/year) to 3Pillar sites and client locations will be required in this role to support ongoing team and client engagement.

What is it like working for 3Pillar Global?

At 3Pillar, we offer a world of opportunity: Imagine a flexible work environment - whether it’s the office, your home, or a blend of both. From interviews to onboarding, we embody a remote-first approach. You will be part of a global team, learning from top talent around the world and across cultures, speaking English every day. Our global workforce enables our team to leverage global resources to accomplish our work in efficient and effective teams. We're big on your well-being - as a company, we spend a whole trimester in our annual cycle focused on wellbeing. Whether it is taking advantage of fitness offerings, mental health plans (country-dependent), or simply leveraging generous time off, we want all of our team members operating at their best. Our professional services model enables us to accelerate career growth and development opportunities - across projects, offerings, and industries. We are an equal opportunity employer. It goes without saying that we live by values like Intrinsic Dignity and Open Collaboration to create cutting-edge technology AND reinforce our commitment to diversity - globally and locally. Join us and be a part of a global tech community!