Operational Enablement Specialist - Canada

About AutoFi AutoFi is the leading provider of digital commerce technology that powers the sales and finance experiences for the most innovative brands and dealers in automotive. The AutoFi platform enables a more transactional buying experience with $4B in funded loans processed through AutoFi annually. AutoFi’s dynamic selling platform empowers dealers to sell vehicles more efficiently and profitably, both online and in the showroom. We are funded for years of future growth and backed by investors including Crosslink Capital, Santander Holdings USA, SVB Financial Group, Ford, BMW iVentures and JP Morgan Chase. Our team is diverse - spread out across the U.S. and Canada, we have backgrounds from finance and technology as well as deep experience in all areas of the auto space. We’re empathetic, gritty, curious, and humble owners of this business and are supported by some of the biggest names in the auto and financial industries as commercial partners. We’ve never been more excited about the opportunity in front of us to help transition the auto industry from offline to online. If changing a trillion-dollar industry sounds exciting, we’d love to hear from you. For more information, visit www.autofi.com. About the Role The Operational Enablement Specialist is expected to play a pivotal role in designing, provisioning and maintaining both foundational and advanced learning experiences that enable operational excellence for both human teams and AI-driven systems.  This role will own the full lifecycle of internal enablement content, inclusive of training an AI Agent to accurately interpret, reason through, and answer complex operational and industry specific questions. You will be responsible for information gathering and analysis through design, development, delivery and continuous improvement across a wide range of topics, including internal systems and tools, as well as successful Product configuration to meet Dealership needs across varying business models and their requirements.  You will create high-quality enablement materials optimized for both human learning and AI comprehension, ensuring consistent, accurate and scalable operational knowledge. Candidates must be self-driven, have the ability to lead, motivate and drive results within cross departmental teams that they do not directly manage. They must have strong communication and presentation skills, be well organized, attentive to fine details, able to work under pressure and have comfort persevering under ambiguity.  Each member of our team is challenged to contribute in a variety of capacities across the entire organization and show their individual strengths, from product to customer experience.  Responsibilities

Participate in building a transparent, cohesive and collaborative team environment with a culture of open communication and feedback.

Locate sources, gather & analyze relevant information, inclusive of deep information gathering with subject matter experts, applications/tools, processes, procedures/SOPs and work instructions etc, for the purpose of uncovering implicit knowledge, assumptions, edge cases in order to develop relevant, robust internal training content and AI Agent enablement materials.

Utilize a hands-on approach to the development of training content related to systems, tools and processes to obtain present state, real-world information and examples, asking questions and digging deep to ensure validity.  Ensure content supports complex question resolution, not just surface-level explanations.

Design and provision foundational onboarding content as well as in-depth, role-specific learning experiences, working with the respective teams to design training solutions in relation to needs expressed, balancing adult learning styles to engage and use individual’s time effectively.

Develop structured learning paths that progress from conceptual understanding to practical application.  Translate complex operational, technical and industry knowledge into clear, consumable learning modules.

Curate training materials including but not limited to written guides, knowledge base articles, videos and quizzes both through our documentation repository as well as our Learning Management System (LMS), aligning elements of training to Process documentation as needed.

Translate nuanced business logic, edge cases and conditional workflows into formats optimised for AI understanding and retrieval.  Curate and refine AI training content to improve reasoning, consistency and contextual awareness.

Ensure content remains accurate, relevant and aligned with evolving business needs over time.  Maintain and regularly update materials to reflect product updates and system changes, ensuring both human teams and the AI Agent are effectively trained on changing standards.

Evaluate and report on training program effectiveness through knowledge assessments, surveys, feedback etc, leveraging findings to refine and enhance these programs, their related materials and improve training effectiveness.

Identify knowledge gaps and opportunities to mitigate business risk through enhanced knowledge, formulate recommendations and prioritize opportunities based on magnitude of undertaking, overall impact & likelihood of achieving desired results within incremental and/or limited timeframes.

Participate in change mgmt activities associated with implementing solutions that require training including coordination between teams, presentations/training, and similar.

Source external training content and courses as appropriate to assist with individual skills development across the Operations org.

Develop data tracking and KPIs to measure the progress and impact of large training initiatives and their evolution over time.

Qualifications

3+ years proven work experience within the Adult Learning, Training & Development discipline

Strong experience designing learning content from scratch and iterating on existing materials.

Experience breaking down complex, ambiguous topics to create clear, structured documentation/training that supports advanced problem solving and decision making

Experience working with AI Agents, chatbots, or knowledge-driven automation systems

Familiarity with prompt design, knowledge structure and AI training methodologies

Ability to work well with technical and non-technical team members at various levels, ranging from support to development

Experience cultivating trust and building relationships interdepartmentally with cross-functional SMEs

Excellent written/verbal communication and presentation skills

Excellent organization, analytical, problem solving and critical thinking skills

Familiarity with Jira, Postman, Salesforce and LMS systems considered an asset

Automotive industry experience and/or familiarity with Dealership business models is a big plus!