Technical Recruitment Manager

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. Own the support function end-to-end—team, process, tooling, and SLA performance

• Serve as the bridge between support and Engineering for triage, escalation, and issue resolution communication
• Implementation Operations
• 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

Partner with RevOps on tooling integrations so customer health, usage signals, and outcomes connect reliably

AI-Enabled Operations

• 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

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
• Bias toward leveraging over building — when facing a capability gap, your first instinct is better tools and playbooks before reaching for a hire
• we're looking for fundamentals and instincts over polish and tenure

Experience leading implementation or delivery teams — operational depth transfers across disciplines

~ 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
Flexible hybrid environment to collaborate in-person at our Toronto HQ.

• Modern employee benefits, including health and dental coverage
• 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. Casual Dress code
• Employee Referral Bonus
• Recruitment Journey at Wisedocs

Our Recruitment process is transparent to ensure you are set up for success:

• Round 1 – People & Culture Chat: 20–30 min conversation about your background, goals, and the role.
• Round 2 – Interview with the Director of Customer Success (30 min)
• Present your take home case study to our Implementation and Support Team Members (1hr)
• Round 4 – Interview with the Hiring Manager: We'll explore your strategic alignment with how we're building technical operations, your leadership philosophy around people development, and whether your collaborative style and instincts fit our culture. (Our target base salary range for this role is $110,000 - $155,000 CAD . This range reflects the full growth journey within the role — from building and developing skills early on, to becoming highly proficient and ultimately achieving excellence. Note: We use AI-powered tools alongside human review to support a fair, inclusive, and efficient hiring process, helping us work smarter and create better experiences for our customers and team.

Even if there isn’t an immediate opening, we’re always excited to meet great people. Wisedocs AI is an equal opportunity employer and are committed to providing employment accommodation in accordance with AODA.