Director of Technical Success

Wisedocs AI•Toronto, ON

3d•CA$110,000 - CA$155,000•Hybrid

About The Position

Wisedocs is a fast-growing, venture-backed AI platform that transforms how insurance companies analyze claims. With ~$20M USD raised, 100+ team members globally, and 90+ customers across North America and Australia, we’re doubling revenue year over year. Founded by experts who’ve experienced the claims process firsthand, Wisedocs combines deep domain knowledge with next-gen AI trained on 100M+ documents. Our platform turns complex medical records into clear, structured insights—backed by expert human oversight. Join a mission-driven team building intelligent products that cut through complexity, accelerate decision-making, and make a real impact when it matters most. We are hiring a Director of Technical Success who will own the infrastructure that delivers Wisedocs’ promise to customers: a support function that resolves fast and learns faster, and an implementation motion that gets customers to first value in 30 days. We are building the technical operations function from the ground up — with a deliberate design for an AI-native future. You'll work as a peer to the CS Director, establishing priorities around customer-facing workflows and tooling jointly. Nothing that touches customer experience is decided in isolation. You'll have genuine authority over support and implementation, real influence over the tooling stack, and the technical fluency to partner with Engineering when needed. The SVP CS serves as the alignment point between your two tracks.

Requirements

3–5+ years leading support engineering or technical support in B2B SaaS — you understand how support infrastructure connects to product and have owned the escalation path to Engineering
Technical fluency (not depth) — you speak Engineering's language well enough to triage with precision and escalate with context; you represent customer impact accurately without needing to be the engineer
AI-forward orientation — you think about AI as an operational lever, not a future state; you've applied AI tools to real workflows, and your instinct is always to ask how AI creates more customer-facing time
People leadership — you invest deliberately in your team, create career paths, and the people who have worked for you have grown
Collaborative working style — you're comfortable with joint decision-making, build alignment naturally, and don't need unilateral authority to move quickly
Cross-functional credibility — you've worked as a peer to CS, Product, or Engineering and know how to build influence without authority
Bias toward leveraging over building — when facing a capability gap, your first instinct is better tools and playbooks before reaching for a hire
Comfort with ambiguity — this may be your first or second Director role; we're looking for fundamentals and instincts over polish and tenure

Nice To Haves

Experience leading implementation or delivery teams — operational depth transfers across disciplines
Experience with support tooling migration or platform selection
Familiarity with CS platforms (Vitally, Gainsight, etc.)
Background in regulated or high-stakes industries (insurance, legal tech, healthcare, financial services) where delivery quality is a trust issue
Experience managing a team through platform rearchitecture or major product expansion

Responsibilities

Own the support function end-to-end—team, process, tooling, and SLA performance
Build an automation plan with the CS Director on what gets automated first and what the team's work looks like after
Serve as the bridge between support and Engineering for triage, escalation, and issue resolution communication
Lead the support tooling rebuild (HubSpot isn't the answer; bring your point of view and execute with CS alignment)
Develop your team and create career paths as the function evolves
Own implementation execution, process design, and delivery standards that consistently hit First Value in 30 days
Partner with CS to evolve the implementation role from coordinators toward launch coaches as AI absorbs coordination work
Design a seamless handoff to ongoing CS so customers experience continuity, not a transition
Administer and optimize the post-sale stack (Vitally, ClickUp, support platform rebuild)
Bring a clear point of view on the right infrastructure for where Wisedocs is heading
Prioritize initiatives in alignment with the CS Director—major roadmap decisions are made jointly
Partner with RevOps on tooling integrations so customer health, usage signals, and outcomes connect reliably
Apply an AI-first lens to every operational problem—freeing teams from transactional work to focus on customers
Build and maintain visibility into AI tools and experiments relevant to post-sale
Work with CS to ensure AI investments serve customer outcomes, not just internal efficiency
Grow into the post-sale function's primary AI operations leader as Wisedocs' AI tooling matures
Build a working relationship with Product with agreed cadence and shared language
Surface patterns from customer issues and bring them to Product in actionable form
Represent the operational implications of product changes before they ship

Benefits

Flexible hybrid environment to collaborate in-person at our Toronto HQ.
Modern employee benefits, including health and dental coverage
Competitive compensation, with valuable stock options, as we’re still a young company growing very quickly.
An opportunity to develop very rapidly in your career. We can offer you a super-immersive learning environment, and when you thrive there, you will have the opportunity to rapidly develop this opportunity into senior practitioner or management opportunities as you choose.
Access to a learning and professional development fund to help you level up your career while you’re working with us. We hope to be an incredible step up in your career if you decide to come and work with us.
Company events
Generous Paid Time Off
Paid Sick Days
Casual Dress code
Employee Referral Bonus
Tuition Assistance
Plus, many other Recognition Programs!