Staff Product Manager

Description

The company's service defines observability and pushes what developer tools can do.

Customers include HelloFresh, Slack, LaunchDarkly and Vanguard, across several industries.

The company has closed Series D funding, grown past 200 people, and was named to Forbes' America's Best Startups list for 2022 and 2023.

The team builds the AI-powered investigation experience. One product area covers Canvas, where engineers query, visualize and understand production systems in natural language, along with Skills (reusable workflows that turn domain expertise into repeatable actions), Auto-Investigations (agent-driven investigations that begin before a person is paged) and a more interactive, collaborative rebuild of Canvas.

Responsibilities

• Set the AI product strategy that supports the company's vision.
• Turn AI trends, customer needs and technical capabilities into clear strategic recommendations.
• Show the product organization where AI creates real customer value and where it is hype.
• Find new observability problems that AI adoption creates, such as LLM drift, prompt regression and low-context generated code.
• Make well-reasoned bets on which AI technologies and approaches deserve investment.
• Run research that connects technology with what customers actually face.
• Learn how customers use AI in their engineering workflows.
• Spot patterns in customer conversations that point to future market needs.
• Track AI and ML developments, including RAG, fine-tuning and agentic systems, and explain what they mean for observability.
• Talk with technical communities, researchers and early adopters to catch trends early.
• Work with product teams to find high-value uses of AI, and advise on approaches, trade-offs and best practices.
• Leave decisions with teams, helping them see how their work fits the AI strategy and which shared capabilities to use.
• Gather cross-portfolio lessons and share what works and what doesn't.
• Explain the link between AI and observability to internal and external audiences, including how observability needs change as customers adopt AI.
• Contribute thought leadership through writing, speaking and community work, earning trust with technical audiences who care how the company uses AI.

Requirements

• 5+ years of product management, including 1+ year shipping AI/ML-powered products.
• A record of taking AI features from concept to customer impact, including ones that failed.
• Working knowledge of how engineering teams build, deploy and run AI systems, beyond theory.
• Familiarity with current AI/ML techniques and the judgment to tell useful ones from overhyped ones.
• Strategic thinking grounded in customer empathy.
• Skill at combining research, customer feedback and technical trends into one coherent strategy.
• Comfort making decisions with incomplete information.
• Ability to notice what customers haven't yet articulated.
• Good judgment about saying 'no' or 'not yet' to exciting technology.
• Enough technical depth to earn respect from engineers and architects, with curiosity and humility about what you don't know.
• Ability to weigh trade-offs between AI approaches, such as RAG versus fine-tuning and model selection.
• Understanding of observability principles and why they matter in production.
• Excellent written and verbal communication, explaining complex ideas to varied audiences.
• Ability to influence product, engineering and go-to-market teams without formal authority.
• Comfort presenting to customers, executives and technical audiences.
• A collaborative style that lifts others' work instead of centralizing control.
• Ability to keep up with fast-moving fields, where AI changes weekly.
• Intellectual humility, valuing learning over being right.
• Interest in where AI meets real customer problems, and energy rather than fatigue from rapid change.

Conditions

The company is fully distributed, so where you sit matters less than how you deliver.

The company invests in its people and cares how you fit its culture and processes.

Trust, autonomy and accountability start on day one.

Remote role.

You will be the product manager for the Canvas and Agentic AI teams, owning the roadmap for how AI shows up in the product, from the UI to the MCP server.

You will work in a close triad with engineering and design leads, and partner with the director of AI strategy, R&D and customer-facing teams.

The role suits someone who can ship production features while working through a product space where the answers are still emerging.

Base salary: $272,739 - $320,829 CAD, based on level and experience.

The company cannot currently sponsor visas or support visa transfers. All hires must verify identity and eligibility to work, as required by law.

Recruiters contact candidates only from company email addresses and never ask for financial or sensitive personal information.

Benefits

• Equity through a generous, employee-friendly stock program.
• Unlimited PTO.
• A stipend covering home office setup, co-working and internet costs.
• Full benefits coverage for employees, with extra coverage available for dependents.
• Paid parental leave of up to 16 weeks, regardless of how you become a parent.
• An annual development allowance.
• Further perks are listed in the original posting.