Principal Product Manager, AI

Principal Product Manager, AI

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Highspot is pioneering the category that is fundamentally changing the way companies increase sales productivity. On a mission to transform the way millions of people work with sales enablement, Highspot is committed to building breakthrough software with a spark of magic. We believe a great place to work is about more than the work – it’s about what the company stands for, and how it authentically represents its values in the real world.

We focus intentionally on creating equitable work spaces for each of our employees, fostering a culture where everyone feels a deep sense of belonging and is empowered to be an agent of change.

In this role, you will be joining the Product Management team reporting to the Director of Product Management in our AI Platform Pillar. You will be working very closely with a senior engineering team and experienced design partners, and over time will help shape and grow not just the product but also the team.

• Define vision & strategy: set the long‑term product vision and multi‑quarter roadmap for Highspot AI capabilities and translate company goals into prioritized opportunities.
• Lead execution end‑to‑end: drive discovery, product design, technical scoping, and delivery with a feature crew of engineers and designers.
• Own model + product success: set metrics, experimentation strategy, and SLA/quality targets, and partner with engineers to evaluate architectures and operationalize monitoring.
• Drive platform & scale thinking: design solutions that are cost‑aware, secure, and easy to adopt by other product teams.
• Champion safety, fairness & compliance: establish guardrails, prompt validation, content filters, and incident playbooks in collaboration with Legal and Security.
• Be the cross‑functional glue: work closely with design, research, engineering, SRE, data science, analytics, sales engineering, and GTM to launch and scale features.
• Mentor & raise the bar: coach other PMs, participate in hiring, and define best practices for ML product management.

• Principal‑level experience with 8+ years shipping products as a PM.
• Experienced at turning ambiguous data into actionable roadmaps.
• Ability to balance multiple data points and stakeholder opinions.
• Strong communicator who can articulate strategy to executives, team members, and customers.
• Technical fluency that allows direct collaboration with senior engineers.
• Comfortable handling many concurrent projects and auto‑prioritizing in high‑growth, ambiguous environments.
• Demonstrated success leading cross‑functional teams to ship high‑quality products.
• Willingness to roll up sleeves and take ownership beyond role definition.
• Strong quantitative analytics and qualitative research skills.

• 8+ years product management experience building B2B SaaS products; 4+ years with ML/AI products or platforms.
• Technical fluency with modern generative AI/ML concepts (LLMs, RAG, embeddings, vector DBs, etc.) and confidence in discussing productionization.
• Proven record of shipping complex, cross‑functional AI products to production that drive measurable business impact.
• Strong quantitative and analytical skills, comfortable defining metrics and designing experiments.
• Exceptional communication skills: write crisp specs, present trade‑offs, and explain technical topics to non‑technical audiences.
• Experience mentoring PMs and participating in hiring.

• Background building platform or infrastructure for other product teams (model‑serving, feature stores, observability).
• Experience with search & recommendation systems or agents at scale.
• Experience with enterprise customers, sales enablement workflows, and AI integration into product flows for customer‑facing teams.
• Familiarity with safety, policy, and compliance work streams (content policies, PII handling, incident response).

Base salary range: $146,000 - $220,000 CAD. Employees are eligible to receive stock options and may also receive other forms of compensation.

• Comprehensive medical, dental, vision, disability, and…