Principal Technical Program Manager

This is a fully remote position, open to applicants in Canada.

📋 Description

• Overseeing substantial, cross-functional projects and programs with an emphasis on the effective delivery of Enterprise and Premium Support services. Responsible for creating and monitoring: Roadmaps, Timelines, Milestones, and managing dependencies across teams.

• Collaborating with sales and revenue teams to enhance attachment, value, and retention of premium support services.

• Proactively identifying technical and operational risks. Managing dependencies between teams and formulating mitigation and contingency plans.

• Leading without direct authority across various departments: Engineering, Product, Revenue, and Support. Facilitating alignment and decision-making while juggling competing priorities.

• Communicating clearly and concisely with all stakeholders.

• Decomposing complex issues into manageable components. Grasping how systems and teams interrelate and foreseeing the downstream effects of decisions.

• Utilizing data to assess process effectiveness and promote continuous improvements.

• Acting as a trusted advisor on program strategy, execution, and operational scaling.

⛳️ Requirements

• A minimum of 8 years of experience in Technical Program Management or Senior Support Leadership positions within a software or SaaS context.

• Experience in delivering high-touch premium support services to large enterprise clients.

• Profound understanding of: Enterprise Support, Premium Support, and High Touch Support operations and delivery.

• Comprehensive knowledge of: AI Agentic Tools (Claude, Codex, Cursor), Cloud platforms (AWS, GCP, Azure), and Support Ticketing Systems (Salesforce).

• Demonstrated success in leading large-scale, complex programs across global teams and organizations.

• Experience in designing and scaling operational processes or delivery frameworks.

• Proven ability to collaborate with revenue and sales teams.

🏝️ Benefits

• Freedom & flexibility; customize your work schedule around your life.

• Designated quarterly Whaleness Days along with an end-of-year Whaleness break.

• Home office setup; we prioritize your comfort while you work.

• 16 weeks of paid Parental leave after 6 months of employment.

• Technology stipend of $100 USD net/month.

• PTO plan that encourages you to take time for personal interests.

• Training stipend for conferences, courses, and classes.

• Equity; as a growing start-up, we want all employees to share in the company’s success.

• Docker Swag.

• Medical benefits, retirement plans, and holidays vary by country.

• Remote-first culture, with offices located in Seattle and Paris.