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. To this end, we have put intentional focus on creating equitable workspaces for each of our employees. Our goal is to create a culture where everyone feels a deep sense of belonging and is empowered to be an agent of change, with the ability to transform themselves, their workplace, and their world.

About The Role

In this role, you will be joining the Product Management team reporting to the Director of Product Management in our AI Platform Pillar. The Product Management function at Highspot is an integral part of the company. You will be jumping into many different projects and features, and will be very hands-on. You will be working very closely with a senior engineering team and experienced design partners. Over time, you will have the opportunity to help shape and grow not just the product, but also the team.

We’re hiring a Principal Product Manager to lead the strategy, execution, and evangelism of AI-first product initiatives that deliver clear customer value at scale. You’ll define the vision and roadmap for a major AI capability — from model selection and data strategy to product UX, and additional platform capabilities— and partner closely with engineering, research, design, GTM and legal to ship safe, reliable, and differentiated AI experiences. This role carries the Principal PM level of ownership: you’ll set strategy across an area of the product portfolio, lead cross-functional feature crews, and raise the bar for product craft and technical rigor.

Our ideal candidate is someone who enjoys understanding a broad set of customer requirements, digging into technical constraints, and using their expertise to deliver an elegantly simple customer experience. This person will benefit from being a skilled communicator, who can drive enterprise-level customer conversations, collaborate effectively with other disciplines, and land proposals with stakeholders.

What You'll Do

Define vision & strategy. Set the long-term product vision and multi-quarter roadmap for Highspot AI capabilities (e.g., model evaluation/monitoring, orchestration, entity detection, recommendation systems, observability, etc.). Translate company goals and customer needs into prioritized opportunities and measurable outcomes.
Lead execution end-to-end. Drive discovery, product design, technical scoping, and delivery with a feature crew of engineers and designers. Make trade-offs to ensure speed and quality while keeping long-term platform health in mind.
Own model + product success. Define model and product metrics, experimentation strategy, and SLA/quality targets. Partner with engineers and research to evaluate architectures (LLMs, RAG, retrieval, embeddings), set up model evaluation pipelines, and operationalize model monitoring and feedback loops.
Drive platform & scale thinking. Design solutions that are performant, cost-aware, secure, and easy for other product teams to adopt. Where relevant, define APIs and tools, data contracts, and telemetry to support product and model lifecycle management.
Champion safety, fairness & compliance. Establish guardrails, prompt / output validation, content filters, and incident playbooks. Work with Legal and Security to ensure data privacy and regulatory compliance.
Be the cross-functional glue. Work closely with design, research, engineering, SRE, data science, analytics, sales engineering, and GTM to launch and scale features. Translate technical tradeoffs into business tradeoffs for executives and stakeholders.
Mentor & raise the bar. Coach other PMs, participate in hiring, and help define best practices for ML product management and technical specwriting.

Your Background

This is a principal-level position. You have been building software products for some time and have 8+ years of experience shipping products as a PM.
You are experienced at taking ideas and ambiguous data, defining the right outcome, and then mapping the right roadmap/backlog to get there.
You are able to consider and balance the many different data points and opinions about your area of ownership.
You can communicate and articulate the strategy and roadmap to execs, team members and customers.
This is a technical role, you will be able to work directly with senior engineers and instinctively understand technical concepts and trade-offs.
You are able to comfortably handle many concurrent projects and todo’s, and instinctively re-prioritize often without needing guidance. Highspot is in a high growth stage and you will be comfortable with the level of ambiguity and workload that entails.
You have worked with engineering teams as a product owner and have demonstrable experience leading cross-functional teams to ship high-quality products.
You have the ability to roll up your sleeves and pick up work outside of your role definition when you need to. You are a strong communicator and can lead teams through difficult decisions.
You have strong data skills in quantitative analytics and qualitative user research.

Minimum Qualifications

8+ years product management experience building B2B SaaS products; 4+ years working directly with ML/AI products or platforms.
Demonstrated technical fluency with modern generative AI / ML concepts (LLMs, RAG, embeddings, vector DBs, fine-tuning, prompt engineering, evaluation metrics, model ops). You don’t have to be an ML engineer, but you must confidently discuss architectures, tradeoffs, and productionization.
Proven record of shipping complex, cross-functional AI products or platforms to production and driving measurable business impact.
Strong quantitative and analytical skills — comfortable defining metrics, designing experiments, and using data to validate hypotheses.
Exceptional communication skills: you can write crisp specs, present tradeoffs to executives, and explain technical topics to non-technical audiences.
Experience mentoring PMs and participating in hiring; a track record of raising the bar for product craft.

Preferred Qualifications

Background building platform or infrastructure used by other product teams (e.g., model-serving, feature stores, observability, inference cost management).
Experience with search & recommendation systems or agents/assistants at scale. (Experience here is especially valuable if the role sits on Agents or Search teams.)
Experience with enterprise customers, sales enablement workflows, and integrating AI into product flows that serve customer-facing teams.
Familiarity with safety, policy, and compliance workstreams (content policies, PII handling, incident response).

Base salary range: $170,435 - $230,435 CAD

Employees are eligible to receive stock options and may also receive other forms of compensation.

The above represents total expected compensation for this role. Actual compensation will depend on various job-related factors, including, but not limited to, location, experience, and job qualifications.

Highspot also offers the following employee benefits for this position:

-Comprehensive medical, dental, vision, disability, and life benefits

-Group Retirement Savings Plan (RRSP) and matching employer contributions (DPSP) with immediate vesting

-Flexible PTO

-Generous Holiday Schedule + 5 Days for Annual Holiday Week

-Quarterly Recharge Fridays (paid days off for mental health recharge)

-Flexible work schedules

-Access to Coaches and Therapists through Modern Health

-2 Volunteer days per year

-Monthly transportation allowance for employees that work in our Vancouver Hub location

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Equal Opportunity Statement

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of any grounds protected by applicable human rights legislation, which may include age, ancestry, citizenship, color, ethnicity, family status, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or invisible disabilities, political belief, race, religion, or sexual orientation.

Did you read the requirements as a checklist and not tick every box? Don't rule yourself out! If this role resonates with you, hit the ‘apply’ button."

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