Senior Product Manager, Platform & AI
About the role:
As a Senior Product Manager at Estateably, you'll own how firms get value from our platform, from the first file they open through the hundredth, and you'll shape where applied AI belongs in fiduciary work. Two connected mandates sit with this role: the product experience that keeps firms coming back, and a new AI product line that changes how the work itself gets done.
You'll set direction rather than take it. You'll decide what the roadmap is for, build the case for it with evidence, and defend the trade-offs when they are contested. You'll work with a dedicated squad, including engineers with their own technical lead, QA, and an accessibility engineer.
This is a senior individual-contributor role reporting to the Director of Product. It has no direct reports. Your influence comes from the clarity of your direction and the quality of your judgment.
What you can expect:
Product strategy and ownership:
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Own the strategy and roadmap for adoption, time to value, and retention across our self-serve and small-firm business. Decide what the team is for, and what it will stop doing.
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Turn first-time users into firms that transact file after file. That is a revenue outcome, and you own the plan behind it.
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Build the investment case with evidence. Connect product decisions to retained and expanded revenue, and make the trade-offs legible to leadership.
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Talk to firms directly, and turn what you hear into a point of view rather than a backlog.
Applied AI:
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Take a new AI product line from early access to a market-ready offering. Define the roadmap, the customer problems it earns its place solving, and how it is packaged and priced.
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Decide how these capabilities reach customers, whether inside the product, through our API, or as something partners build on.
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Set the bar for trustworthiness in a domain where a wrong answer has consequences. Accuracy, transparency, and human review are product decisions here, not engineering details.
Quality and accessibility as commercial levers:
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Own the standard for what ships. Product quality is a growth lever rather than a cleanup exercise, because friction in the experience shows up directly in repeat volume.
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Own accessibility as a product commitment, working alongside a dedicated accessibility engineer, so it is designed in rather than remediated later.
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Define the measures that show whether the experience is genuinely improving, and hold the team to them.
Cross-functional leadership:
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Partner with engineering leadership on sequencing and capacity, and make the call when two priorities want the same team at the same time.
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Work closely with Design, Engineering, Leadership, and QA.
- Represent the product to customer-facing teams and to leadership, and escalate cross-cutting decisions rather than absorbing them.
What we're looking for:
Must-haves:
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6+ years in product management, including at least one product area you owned end to end: strategy through outcome, not feature delivery inside someone else's roadmap.
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Comfortable carrying an established product and something new at the same time, without letting either drift.
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A working point of view on applied AI: where it genuinely helps, where it falls short, and what earns a customer's trust.
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Strong quantitative judgment. You can build the revenue case for a retention or quality investment and feel confident leading change to accomplish it.
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Fluency running discovery, and the communication to bring Engineering, Design, and customer-facing teams to one picture. Comfortable working from incomplete information, and giving and taking direct feedback openly.
Nice to have:
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Experience taking a new product or capability from early access to a commercial offering, including packaging and pricing.
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Experience in a complex, workflow-heavy domain (legal, fintech, enterprise SaaS, or similarly dense problem spaces); legal tech, estate or trust administration, or accounting workflows especially.
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Experience treating accessibility as a product commitment rather than a compliance exercise.
Why Estateably:
Over the next 25 years, more than $60 trillion will be transferred between generations, yet professionals and the families they serve are wholly underserved in their tools to navigate the estate and trust administration process. Estateably was founded to change that.
Here's why you'll want to be part of it:
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Massive market opportunity: We're tackling one of the largest wealth transfers in history, in an industry overdue for transformation.
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Rapid growth and adoption: Since launching in 2021, we've become the fastest-growing estate and trust platform in North America, serving 1,000+ firms across Canada and the U.S.
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Real problems, real impact: Our platform helps fiduciaries handle complex, sensitive workflows that directly affect professionals and their practices.
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Bold, ambitious vision: We're not here to make small improvements—we're rethinking how the industry works from the ground up.
What our team has in common:
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A hunger to learn fast and continuously.
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High ownership and accountability for results.
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A can-do, solution-oriented mindset.
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Strong collaboration skills and a team-first attitude.
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Comfort with change and fast-paced environments.
Perks & Benefits:
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Flexible hours & remote work.
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Participation in our company's Employee Stock Option Plan.
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Yearly bonus based on performance.
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Full participation in our company's group health, dental, and virtual medicine plans.
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Wellness Benefit.
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Computer equipment.
Please note that this is a 12-month employment term, with the possibility of extension at the company's discretion. Proficiency in English is required for this role due to regular collaboration with clients and internal team members across Canada and the U.S.
