Technical Product Strategist

Looking to evolve a proven product with new technology that measurably boosts adoption and everyday value?

We’re searching for a Technical Product Strategist to help us adapt our existing platform with responsible, high‑impact features that improve discovery, clarity, and productivity: accelerating activation, engagement, and retention across our customer base. This includes a focus on content curation and discovery. You’ll turn promising product concepts into pragmatic strategies, clear technical requirements, and measurable feature implementations that customers love. This role involves analyzing market needs, defining the technical roadmap for strategic product enhancements, and collaborating closely with engineering and design teams to ensure successful, customer‑centric feature delivery.

This role is based in the Greater Vancouver area, offering a blend of remote work and in‑office collaboration. You will be part of a tight‑knit team and have the option to work from our Vancouver office. While the majority of your work will be conducted remotely, periodic in‑office attendance will be required for essential activities like team‑building, strategic planning, and celebrations, as determined by your team lead.

Jostle is committed to providing fair compensation, equity, and benefits. The salary offered for this role is $80,000 to $140,000 and will be based on the candidate’s experience and expertise. For a full list of benefits, please continue scrolling below. Come join us—we’re excited to meet you, and thank you for considering Jostle

What you’ll do:

- Identify and prioritize opportunities that enhance user flows, translating product needs into strategies, roadmaps and plans aligned to measurable adoption outcomes and customer value.

- Lead AI discovery and experiments on existing features and user journeys: define hypotheses, metrics, user evaluations and post‑launch reviews.

- Establish guardrails for responsible AI: data handling, bias assessment, safety policies, human‑in‑the‑loop validation, and transparent user messaging.

- Audit and critique end‑to‑end user experiences and product flows, identifying opportunities for refinements and AI assistance to enhance usability and adoption.

- Develop strategies for knowledge capture, knowledge base management, content curation, and contextual relevance to support AI‑driven features and broader platform utility.

- Coordinate and document AI directions and improvements, including cross‑functional enablement materials, customer‑facing documentation, model choices, prompt patterns, and evaluation methods.

- Partner with the Development team and the System Architect to define technical requirements.

- Audit our customer‑facing experiences and analyze gathered competitive intelligence.

What you’ll need:

- Proven ability to:

- observe, clarify, and deeply understand user needs in AI‑augmented workflows within an existing product.

- problem‑solve, design, and refine end‑to‑end AI experiences with a focus on usefulness, safety, and measurable adoption, efficiently use product, data, and communication tools to deliver well‑crafted solutions.

- evaluate, integrate, and effectively use existing AI tooling and platforms to enhance product functionality and team efficiency.

- work within constraints of established standards (privacy, accessibility, brand, platform).

- Experience using AI features (LLM‑powered search/assistants, retrieval/ranking, summarization, or recommendations) in production.

- Familiarity with fast‑paced, collaborative environments and co‑creation practices, including being comfortable with critique and knowing how to seek or provide it.

- Excellent organizational and communication skills: both written and verbal.

- Strong technical skills and a proven ability to think logically: an ability to break down complex problems and describe them to others.

- At least 3 years of experience in product management and/or product strategy.

- Comfort collaborating across disciplines including design, engineering, data, QA, marketing, and support.

- A sharp eye for detail and eagerness to contribute to clarity, consistency, and trust.

- Legally able to work in Canada.

What would come in handy:

- A relevant post‑secondary degree or diploma.

- Hands‑on familiarity with LLMs, embeddings, RAG architectures, evaluation methods, and prompt engineering.

- Some experience with statistical analysis and modeling tools.

- Case studies demonstrating improved adoption from AI enhancements to existing products.

- Experience in a company delivering rich software to users around the world.

- Previous remote working experience is a plus.

What we’d love to see:

We know that applying to a new role takes a lot of work and we’re looking forward to reading your application. Please be sure to send us samples of your work: strategy docs, PRDs, evaluation plans, experiment results, demos, or whatever represents what you do best.

What we offer:

- A collaborative and friendly hybrid workplace, mostly remote.

- Extended health and dental benefits (including mental health support).

- Profit sharing.

- Frequent socials.

- Every other Friday is yours. Seriously. Our reduced work schedule gives you 26 bonus days off each year—built‑in time to breathe, create, or just do you. All without dipping into your PTO.

About Jostle:

Jostle’s platform is where everyone connects, communicates, and celebrates at work. It’s the heartbeat of our own company and has helped employees in over 1,000 organizations easily belong and contribute, anywhere, anytime. With industry‑leading participation rates, we’re putting the joy back into work and the life back into organizations.

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