Principal Technical Program Manager at MaintainX in Canada

MaintainX is the world's leading AI-powered maintenance and asset management platform, serving 13,000+ customers including Duracell, Shell, Cintas, and Brenntag. We raised $150M in Series D funding led by Bessemer Venture Partners and Bain Capital Ventures, bringing our total funding to $254M. We were named to the Forbes 2025 Cloud 100, the definitive ranking of the top 100 private cloud companies in the world. We are seeking a Principal Technical Program Manager to drive our most complex, cross-functional engineering initiatives. You'll own a portfolio of programs spanning Core product, AI/ML, Platform, Infrastructure, and Enterprise — operating as a peer to our senior engineering leaders and influencing without direct authority. This is a senior individual contributor role. What You’ll Do Own end-to-end execution of company-critical programs that span Core product, AI/ML, Platform, Infrastructure, and Enterprise teams. Lead design and delivery of highly complex initiatives in ambiguous or new technology areas; make tradeoffs across scope, quality, timing, and architectural debt. Establish OKRs, KPIs, and the operating rhythm (planning, reviews, retros, exec updates) that keep a fully distributed engineering org aligned and shipping. Surface cross-team risks early, provide escalation management, and steer teams away from prior failure patterns. Create scalable mechanisms and methodologies that hold up as the engineering org grows. Author strategy narratives, program plans, and exec memos; present to leaders two and three levels above with the clarity expected at the principal level. About You 10+ years managing technical programs across cross-functional engineering teams. 3+ years operating at a principal or staff level driving multi-org programs. Experience leading complex programs in at least three of: infrastructure or platform, AI/ML, consumer or frontline products, and enterprise/B2B. Experience defining KPIs and SLAs and reporting program outcomes to executive leadership. Preferred Qualifications Experience shipping AI/ML-powered products or working with foundation models. Experience scaling platform or infrastructure teams through hypergrowth. Experience supporting an upmarket motion to Fortune 5000 customers. Track record authoring strategy narratives and exec memos that drive decisions. Demonstrated track record of using AI tools (Claude, ChatGPT, etc) to scale your own throughput as a TPM. What’s In It for You Competitive salary and meaningful equity opportunities. Healthcare, dental, and vision coverage. 401(k) / RRSP enrollment program. Take-what-you-need PTO and flexible work culture. A Work Culture where: You'll work alongside folks across the globe that reflect the MaintainX values, Smart Humble Optimist. We believe in meritocracy, where ideas and effort are publicly celebrated. About Us Our mission is to make the lives of blue-collar workers easier worldwide by creating software that meets their needs and realities. Our product is truly life-changing for 80% of the workforce that doesn’t work behind a desk and needs enterprise-grade software at their fingertips. MaintainX is committed to creating a diverse environment. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. #LI-Remote