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Director of Technical Success
Wisedocs · Toronto, Canada
About The Role
Join Wisedocs as the Director of Technical Success, where you will lead the development of our technical operations function and ensure a seamless customer experience. You will own the support function end-to-end, lead the support tooling rebuild, and oversee implementation execution. This role requires strong leadership skills, technical fluency, and a bias towards leveraging AI as an operational lever.
- Own the support function end-to-end, including team management, process improvement, tooling, and SLA performance.
- Lead the support tooling rebuild and develop an automation plan in collaboration with the Customer Success Director.
- Partner with Customer Success to evolve the implementation role and ensure a seamless handoff to ongoing customer support.
- Collaborative working style — you're comfortable with joint decision-making, build alignment naturally, and don't need unilateral authority to move quickly
- 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
- Cross-functional credibility — you've worked as a peer to CS, Product, or Engineering and know how to build influence without authority
- Comfort with ambiguity — this may be your first or second Director role; we're looking for fundamentals and instincts over polish and tenure
- People leadership — you invest deliberately in your team, create career paths, and the people who have worked for you have grown
- Bias toward leveraging over building — when facing a capability gap, your first instinct is better tools and playbooks before reaching for a hire
- 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
- 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
- Experience leading implementation or delivery teams — operational depth transfers across disciplines
- Familiarity with CS platforms (Vitally, Gainsight, etc.)
- Experience with support tooling migration or platform selection
- 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
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