Director of Product — Ecosystem

❗This is a Full-time permanent position 

❗This is a new position 

📍Location: This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office, located at 351 King St E, Suite 1100, Toronto, ON. 

Third-Party Ecosystem Strategy 

• Lead Caseware’s third-party ecosystem strategy and keep it current as the market moves. 

• Understand the technology solution landscape and the determine the priority of partnerships and integrations across customer integration use cases and third-party technology integrations 

• Bring the evidence behind those decisions: firm technology-stack data, customer demand signals, and competitive position. 

• Set out the strategy for senior leadership and the trade-offs within it. 

Ecosystem Product Surface 

• Own the roadmap for the ecosystem product surface – inclusive of interoperability capabilities, integrations, connectors, marketplace, and developer tooling. 

• Identify and communicate delivery risks against the roadmap. 

• Own the marketplace as a product surface, including how partners and their capabilities are presented and discovered. 

• Decide what enters the ecosystem surface and what is deprecated. 

Build, Buy, or Partner Framework 

• Own the build, buy, or partner framework and apply it to ecosystem capability decisions. 

• Maintain the classification that determines whether a capability is built, acquired, or partnered. 

• Produce the analysis and recommendation behind each decision, including the case for the option not taken. 

• Take recommendations through to a decision with senior leadership, working with corporate development and finance where the answer is to acquire or invest. 

Interoperability Requirements and Integration Workflows 

• Lead the understanding of what interoperability capabilities customers and partners need and translate it into product requirements – inclusive of Agentic Interoperability 

• Define the integration workflows Caseware supports, and the technical standards an integration must meet. 

• Manage integrations as products, with defined adoption targets, quality expectations, and support models. 

• Recruit and run design partners to validate integrations before general availability. 

Third-Party Developer Experience 

• Lead on the experience of third parties building against Caseware, and inform the product requirements for the APIs, SDKs, documentation, and tooling they use. 

• Define what self-service onboarding looks like for a partner or customer developer. 

• Advocate for the platform capabilities the ecosystem surface depends on, including security, performance, and extensibility. 

Partner Program Design 

• Design the partner program, covering intake, evaluation, certification, and the marketplace. 

• Set the bar a partner must meet to be certified, and the criteria applied at intake. 

• Define partner onboarding and enablement so partners can integrate at scale 

• Define the operating model for the program, including governance, tooling, and reporting cadence. 

Working with Engineering 

• Partner with engineering on interoperability requirements, technical standards, and sequencing. 

• Provide the customer and market context behind each requirement, not only the requirement. 

• Surface trade-offs and constraints that affect roadmap commitments, and agree the path through them. 

Commercial Collaboration 

• Provide the product and technical position into partner contracting and negotiation. 

• Contribute to the ecosystem monetisation model, including marketplace, referral, and revenue-share approaches. 

• Work with Legal on NDAs, term sheets, and the technical terms of partnership agreements. 

Go-to-Market and Customer Enablement 

• Work alongside Sales, Support, and Marketing on go-to-market for ecosystem capabilities. 

• Inform product positioning and the market narrative for the ecosystem. 

• Define the ecosystem performance measures and report against them on a set cadence. 

Team Leadership 

• Lead and grow the ecosystem product team as the ecosystem scales. 

• Set the standard for how the team defines requirements, sizes opportunity, and reports delivery risk. 

• Represent the partner and developer perspective within Caseware. 

• 8+ years in product management, including ownership of platform, integration, or ecosystem products. 

• Experience owning a roadmap for a product surface used by third parties. 

• Working knowledge of API-based integrations, MCP, interoperability standards, marketplaces, and developer experience. 

• Experience applying a build, buy, or partner framework, including evaluating partnerships or acquisitions. 

• Experience defining a partner program, including intake and certification criteria. 

• Commercial fluency: able to contribute to contracting and monetisation decisions without owning them. 

• Able to set out a product strategy and the evidence behind it to a senior audience. 

• Comfortable operating with ambiguity, and willing to set direction and do the hands-on work. 

• People leadership experience, or a clear appetite to build and lead a team over time. 

• Experience in audit, accounting, or professional services software is an asset. 

• Bachelor’s degree in Business, Technology, or a related field.