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About the Role

Wisedocs is seeking a Director of Technical Success to own the infrastructure for customer support and implementation, ensuring fast resolutions and rapid value realization. This role involves building the technical operations function from the ground up with an AI-native future in mind, working collaboratively with the CS Director and Engineering.

Responsibilities

• Own the support function end-to-end, including team, process, tooling, and SLA performance.
• Develop an automation plan for the support team in collaboration with the CS Director.
• Serve as the liaison between support and Engineering for issue triage, escalation, and resolution communication.
• Lead the rebuild of the support tooling platform.
• Develop the support team and create career paths.
• Own implementation execution, process design, and delivery standards to achieve First Value within 30 days.
• Partner with CS to evolve the implementation role towards launch coaches as AI handles coordination.
• Design a seamless handoff process from implementation to ongoing CS.
• Administer and optimize the post-sale technology stack, including Vitally, ClickUp, and the support platform.
• Contribute a clear point of view on the optimal infrastructure for Wisedocs' future.
• Prioritize initiatives in alignment with the CS Director for joint roadmap decisions.
• Partner with RevOps on tooling integrations to ensure reliable connection of customer health, usage signals, and outcomes.
• Apply an AI-first approach to operational challenges to free teams from transactional work.
• Build and maintain visibility into AI tools and experiments relevant to post-sale operations.
• Collaborate with CS to ensure AI investments support customer outcomes.
• Grow into the primary AI operations leader for the post-sale function.
• Build a working relationship with Product, establishing a cadence and shared language.
• Surface patterns from customer issues and communicate them to Product in an actionable format.
• Represent the operational implications of product changes before they are released.

Requirements

• 3–5+ years leading support engineering or technical support in B2B SaaS.
• Understanding of how support infrastructure connects to product and ownership of the escalation path to Engineering.
• Technical fluency to triage with precision and escalate with context.
• Ability to represent customer impact accurately.
• AI-forward orientation, viewing AI as an operational lever and applying AI tools to real workflows.
• People leadership experience, including investing in team development and creating career paths.
• Collaborative working style, comfortable with joint decision-making and building alignment.
• Cross-functional credibility, with experience working as a peer to CS, Product, or Engineering.
• Bias toward leveraging existing tools and playbooks over building new solutions.
• Comfort with ambiguity, suitable for a first or second Director role.

Skills

• Technical Fluency
• AI-forward orientation
• People Leadership
• Collaborative working style
• Cross-functional credibility
• Leveraging over building
• Comfort with ambiguity

Location

• Toronto HQ

Work Type

• Hybrid

Experience Level

• Director
• 3-5+ years

Salary/Compensations

• 110,000 - 155,000 CAD

Benefits

• Flexible hybrid environment
• Modern employee benefits, including health and dental coverage
• Competitive compensation with valuable stock options
• Opportunity for rapid career development and learning
• Access to a learning and professional development fund
• Company events
• Generous Paid Time Off
• Paid Sick Days
• Casual Dress code
• Employee Referral Bonus
• Tuition Assistance
• Recognition Programs

About the Company

• Wisedocs is a fast-growing, venture-backed AI platform transforming how insurance companies analyze claims.
• Approximately $20M USD raised, with over 100 team members globally.
• Serves over 90 customers across North America and Australia, with year-over-year revenue doubling.
• Founded by experts with firsthand experience in the claims process.
• Combines deep domain knowledge with next-gen AI trained on over 100M documents.
• Platform turns complex medical records into clear, structured insights with expert human oversight.
• Mission-driven team building intelligent products that cut through complexity, accelerate decision-making, and make a real impact.

Equal Opportunity

• Wisedocs AI is an equal opportunity employer and is committed to providing employment accommodation in accordance with AODA.
• If you require an accommodation, please notify us and we will work with you to meet your needs.