Customer Enablement Specialist

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.   

Role Summary 

We're hiring a Customer Enablement Specialist to build and scale how customers learn and get value from our platform. This role sits within Customer Success and owns our self-serve content experience — from knowledge base governance to short-form video and task-based guides — making it easy for customers to adopt our product independently, at their own pace. 

Our platform serves a wide range of personas (adjusters, paralegals, lawyers, IME Doctors, nurse evaluators, and clerical staff) across complex enterprise organizations, so content must be persona- and workflow-driven: modular, right-sized, and built to scale with the product. Live training for strategic accounts is part of the role, but the primary focus is scalable, self-serve enablement. 

Looking ahead, we're evaluating an LMS to further organize and scale learning paths — and this role will be central to that effort. 
 
What you'll be doing 

 Build and own the self-serve enablement experience 

• Own the structure, quality, and governance of our knowledge base — including taxonomy, templates, style standards, and release updates. 

• Produce short-form content across formats: articles, quick-start guides, GIFs, short videos, and task-based job aids. 

• Translate product features and workflows into clear, persona-specific content for each user type (adjusters, legal, clinical, clerical). 

Design persona-based content and learning paths 

• Develop learning paths mapped to real workflows — onboarding, new feature rollouts, and common how-to tasks — properly scoped with clear objectives and steps. 

• Partner with Product, Support, and CS to keep content accurate and aligned with product releases. 

• Apply content design best practices to support different learning styles across written, visual, and live formats. 

Support strategic account enablement 

• Design and facilitate live enablement sessions for strategic accounts, tailoring delivery for mixed audiences. 

• Build training plans aligned to customer goals and personas, reusing standardized modules wherever possible. 

• Feed insights from live trainings back into self-serve resources to reduce repeat enablement needs over time. 

Scale content operations and measure impact 

• Track KB usage, training feedback, and adoption signals to understand what's working and where to improve. 

• Contribute to LMS evaluation and rollout if we proceed — including requirements, content migration, and pilot planning. 

• Apply AI tooling to scale content production responsibly, including establishing governance standards for quality and review. 

You're a great candidate if you have 

•  5+ years in customer education, product enablement, content design, or curriculum development with a strong bias toward self-serve and scalable formats. 

• Proven ability to produce short-form content — video walkthroughs, interactive guides, task-based job aids — that reduces support and CS dependency. 

• Experience owning curriculum development end-to-end in a SaaS environment, translating software workflows into clear, task-based learning. 

• Experience supporting strategic accounts or large user communities with diverse roles and needs. 

• Strong content design instincts: clear objectives, right-sized modules, reusable components, and multiple modalities (written, video, live, interactive). 

• Excellent written and verbal communication skills with the ability to make complex processes clear and approachable. 

Nice to have 

• Experience in a regulated industry such as healthcare, insurance, legal, or finance. 

• Experience creating content for clinical or legal audiences (IME providers, claims teams, law firms). 

• Familiarity with KB governance or LMS evaluation and implementation. 

What we offer 

• Flexible hybrid environment with the option 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!   

Recruitment Journey at Wisedocs   

We're excited to meet you and explore the possibilities together!  At Wisedocs, honesty is one of our core values. 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.  

• Between Rounds 1 & 2 – Take-Home Exercise: If you move forward, our People & Culture team will send you a take-home case study to prepare in advance of your next interview 

• Round 2 – Interview with the Enablement Manager: You’ll present your prepared take-home case study and discuss your approach, thought process, and recommendations (1 hr) 

• Round 3 – Interview with the Director of Customer Success: Deep dive into your experience and problem-solving approach (45 mins)  

• Round 4 - Leadership Conversation: Meet our SVP of Customer Success to learn about their vision and your impact (30 min) 

Compensation  

The total on-target earnings (OTE) range for this position is $60,000 - $100,000 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. Where an offer lands within the range is based on your experience, skills, and impact, which we assess throughout the hiring process.   

We’re committed to fair and transparent pay and ongoing career development. If your expectations fall outside this range but you’re excited about the role, we still encourage you to apply.   

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.  

This posting is for current and future opportunities at Wisedocs. Even if there isn’t an immediate opening, we’re always excited to meet great people. If your experience lines up, we encourage you to apply — we’ll reach out when a role opens that’s a good fit.  

*Wisedocs AI is an equal opportunity employer and are 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.