Principal Technical Program Manager (AI)

TL;DR

Principal Technical Program Manager (AI/ML/Platform): Driving complex, cross-functional engineering initiatives across Core product and Infrastructure with an accent on end-to-end execution and strategic alignment. Focus on establishing operating rhythms, managing cross-team risks, and scaling mechanisms for a distributed engineering organization.

Location: Remote (United States & Canada)

Company

AI-powered maintenance and asset management platform serving over 13,000 customers globally.

What you will do

• Own end-to-end execution of critical programs spanning Core product, AI/ML, Platform, Infrastructure, and Enterprise teams.
• Lead the design and delivery of complex initiatives in ambiguous technology areas, managing tradeoffs between scope, quality, and architectural debt.
• Establish OKRs, KPIs, and operating rhythms to keep a distributed engineering organization aligned and shipping.
• Identify cross-team risks early and provide escalation management to steer teams away from failure patterns.
• Develop scalable mechanisms and methodologies to support the growth of the engineering organization.
• Author strategy narratives and executive memos for leadership.

Requirements

• 10+ years of experience managing technical programs across cross-functional engineering teams.
• 3+ years of experience operating at a principal or staff level driving multi-org programs.
• Proven experience in at least three of the following: infrastructure/platform, AI/ML, consumer/frontline products, or enterprise/B2B.
• Experience defining KPIs and SLAs and reporting outcomes to executive leadership.
• Must be based in the United States or Canada.

Nice to have

• Experience shipping AI/ML-powered products or working with foundation models.
• Experience scaling platform or infrastructure teams during hypergrowth.
• Track record of supporting an upmarket motion to Fortune 5000 customers.
• Proficiency in using AI tools (e.g., Claude, ChatGPT) to increase TPM throughput.

Culture & Benefits

• Competitive salary and meaningful equity opportunities.
• Comprehensive healthcare, dental, and vision coverage.
• 401(k) / RRSP enrollment programs.
• Flexible work culture with "take-what-you-need" PTO.
• Meritocratic environment that values "Smart Humble Optimist" traits.