Strategic Technical Program Manager

Accountabilities: Own end-to-end internal coordination of complex customer product deliverables across Product, Engineering, and Customer Success, identifying blockers and risks early. Partner with Product Managers to ensure customer commitments are fully scoped, appropriately resourced, and sequenced within the product roadmap. Work closely with Customer Success Managers to align internal delivery plans with customer expectations, proactively addressing risks, dependencies, and potential scope or timeline conflicts. Lead and operationalize user acceptance testing (UAT), coordinating customer participation, success criteria, feedback, and timelines. Establish clear program plans, milestones, delivery rhythms, and accountability across cross-functional teams. Track program scope, execution status, risks, dependencies, decisions, and resource alignment using effective tools and processes. Define and monitor success metrics that connect delivery milestones to customer value realization, including activation, first value, and adoption. Create and manage customer-facing communications, including executive-level program updates, status reporting, and scope-change communications. Maintain a consistent cadence of concise, transparent updates that give customers and internal leadership clear visibility into progress and program health. Collect, synthesize, and communicate post-delivery customer feedback to support continuous improvement and inform future product roadmap decisions. Facilitate scoping discussions, feedback cycles, and difficult stakeholder conversations while balancing customer expectations, technical constraints, timelines, and business priorities. Identify conflicts and emerging issues early, negotiate practical solutions, and prevent risks from escalating into larger delivery problems. Build scalable program management practices that allow multiple enterprise programs to be managed effectively without unnecessary executive intervention. Develop strong working relationships with Product Managers, Engineers, Customer Success leaders, customers, and other senior stakeholders. Requirements 5+ years of experience in technical program management, program management, or customer-facing project/program roles within SaaS or enterprise software environments. Demonstrated ability to lead complex, multi-stakeholder programs involving both technical teams and customers. Strong understanding of agile software development , including sprint planning, backlog management, development cycles, and delivery rhythms. Ability to communicate effectively with engineers, product managers, customer success professionals, executives, and external customers. Excellent written communication skills, with the ability to produce concise, structured, and actionable status updates. Strong facilitation and negotiation skills, including the confidence to lead difficult conversations and push back constructively when priorities conflict. Highly organized, proactive, and outcomes-focused, with the ability to introduce structure and clarity into complex or ambiguous situations. Strong risk-management skills and the ability to identify dependencies, conflicts, and potential delivery issues before they escalate. Experience leading scoping discussions, UAT processes, customer feedback cycles, and post-delivery improvement initiatives. Comfortable working across competing priorities while maintaining focus on contractual commitments and customer outcomes. Systems-oriented thinking, with an ability to understand edge cases and connect individual deliverables to broader business and customer objectives. Strong customer-facing presence and the ability to build trust through transparency, reliability, and consistent follow-through. Experience working with large enterprise or Fortune 1000 customers is an asset. Familiarity with B2B SaaS workflows, particularly within engineering, manufacturing, or other technically complex industries, is an asset. Comfortable working independently in an environment where ambiguity, changing priorities, and complex stakeholder dynamics are part of the role. Eligible to work in Canada or the United States , with the position designed for candidates located within North America. Benefits Full-time, permanent employment with a competitive compensation package. Stock options , providing an opportunity to participate in the company's long-term growth. Extended health and benefits coverage . Unlimited paid vacation . RRSP or 401(k) matching , depending on eligibility and location. Remote work flexibility from anywhere within North America. Preference for candidates located within the Pacific Standard Time (PST) zone to support collaboration across teams. Opportunity to work directly with major enterprise customers on complex technical product programs. Cross-functional exposure to Product, Engineering, and Customer Success teams. Significant ownership and influence over program management processes, delivery practices, and customer experience. Opportunity to help establish scalable processes and operating models as the organization continues to grow. An environment that values proactive ownership, continuous learning, clear communication, and practical problem solving.