Director of Technical Success

Wisedocs

Director of Technical Success at Wisedocs overseeing support and implementation functions. Leading AI-driven operational strategies for enhancing customer success and experience.

Posted 7/6/2026full-timeToronto • 🇨🇦 CanadaLead💰 CA$110,000 - CA$155,000 per yearWebsite

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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

Benefits

Comp & perks

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!

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

Support Infrastructure ManagementTechnical FluencyAI Tool ApplicationProcess OptimizationEscalation Path Ownership

Soft Skills

Collaborative Working StyleComfort with AmbiguityInfluence Without Authority