Head of Wealth Solutions, Canada at Feathery in Toronto, Ontario, CA

About Feathery

Feathery is the AI Operating & Decisioning system for financial services. Leading financial institutions, including Fortune 500 companies, use Feathery to power mission-critical workflows across wealth management and insurance, such as client onboarding, account opening, advisor transitions and repapering, compliance data collection, and client servicing.

Why We're Hiring

As Feathery expands its work with leading financial institutions, we're building a dedicated Wealth Solutions practice in Canada. We're looking for a senior wealth leader who can bring deep industry expertise, trusted relationships, and a strong understanding of how Canada's leading wealth organizations operate.

This is an opportunity to play a defining role in Feathery’s Canadian wealth practice at a pivotal stage of growth, working with some of the country's leading financial institutions and helping shape how they modernize critical workflows and adopt new technology.

About the Role

As Head of Wealth Solutions, Canada, you'll be Feathery's in-house wealth management expert and a key leader of our Canadian wealth practice. You'll partner closely across Sales, Solutions Engineering, Product and Delivery, bringing deep wealth expertise to the opportunities and decisions that matter http://most.You'll originate and lead strategic opportunities, build and deepen high-value relationships across Canada's leading wealth organizations, champion adoption across key accounts, and represent the wealth customer in go-to-market decisions.

Your industry expertise, perspective, and established network across Canada's wealth management ecosystem will be core assets in this role.

What You'll Do

Strategic Client Advisory

• Serve as Feathery's wealth domain expert in strategic client conversations, bringing industry context and operational depth to complex opportunities and helping address buyer-side strategic and operational questions.
• Explain how Feathery's products map to core wealth management workflows, including client onboarding, account opening, KYC and suitability reviews, advisor servicing, document collection, and operational processing.
• Advise clients on rethinking critical operational processes, driving meaningful workflow transformation rather than sitting on top of legacy steps.
• Navigate wealth-specific client objections across regulatory, compliance, data security, and governance requirements, and demonstrate how Feathery operates within them.
• Drive demo enablement alongside Solutions Engineering, ensuring wealth demos reflect real-world workflows and resonate with senior buyers, while building domain fluency across AEs and Solutions Engineers.
• Codify post-sales best practices from wealth implementations into repeatable playbooks and reusable assets the broader team can apply across accounts.

Client Adoption & Growth

• Equip and coach client champions to drive adoption, retention, and expansion, and build the case for Feathery across their organizations.
• Identify opportunities to extend Feathery into additional workflows and use cases across wealth accounts.
• Serve as the bridge between wealth clients and Feathery, bringing industry context, client priorities, and unmet needs back to Product, Sales, and Delivery.

Strategic Partnerships & Co-Sell

• Own and build Feathery's partnership and co-sell motion across Canadian wealth management.
• Build and activate relationships across the Canadian wealth market to create strategic opportunities, warm introductions, partnerships, co-sell opportunities, and market intelligence.

Product Roadmap & Industry Insight

• Bring wealth domain expertise and client insight to Product and Engineering, helping shape and prioritize the roadmap through a wealth management lens.
• Pressure-test proposed features using domain expertise and direct client feedback, ensuring product direction reflects real market needs.

Market Strategy & Thought Leadership

• Partner with Product Marketing to shape wealth positioning, messaging, and Feathery's go-to-market narrative for the Canadian market.
• Represent Feathery at relevant industry and partner events, and strengthen Feathery’s industry presence through content and thought leadership.

About You

• 10+ years of experience in Canadian wealth management, ideally at the Director or VP level in wealth operations within a major bank, private wealth business, investment dealer, asset manager, or wealth management platform.
• Strong understanding of wealth management workflows, operating models, and industry dynamics, with the domain fluency to engage credibly across the organization.
• An established network across Canada's wealth management ecosystem, with trusted senior relationships and the ability to evangelize Feathery at industry events and across the market.
• Operationally savvy, with experience leading transformation within wealth management, including evaluating and implementing new solutions and driving adoption.
• Strong understanding of the regulatory, compliance, and change-management considerations involved in introducing new solutions within complex financial institutions.
• Good Commercial instincts and a functional consulting mindset: able to identify opportunities, shape practical solutions, and build alignment across stakeholders.
• Strong communication and the gravitas to engage senior wealth leaders as a peer, while remaining hands-on.

Bonus

• Experience with AI, workflow automation, document intelligence, or other emerging technologies relevant to wealth management.
• A background in or experience working alongside wealthtech, fintech, consulting, or enterprise software companies.
• A track record of building strategic partnerships or co-sell relationships within financial services.
• Experience operating across both a large financial institution and a high-growth technology environment.
• Cross-industry experience spanning wealth management and insurance.

What We Offer

• Competitive compensation and equity
• Health, dental, and vision coverage
• Unlimited PTO
• Downtown Toronto office location
• Office snacks and lunches
• A supportive, low-ego team that values ownership and growth
• Company offsite to connect and recharge

If you’re excited about helping wealth management organizations modernize critical workflows — and want to lead our growth as a category leader in Canada — we’d love to meet you.

Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.