About Highspot
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.
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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).
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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."
