Customer Support & Enablement Lead

About the Role

PolicyBook is looking for a Customer Support & Enablement Lead to own the full post-sale customer experience — from onboarding through day-to-day support. This is a hybrid role that blends hands-on ticket resolution with building the systems, content, and processes that let distributors and advisors get real, ongoing value from our platform. You'll sit at the intersection of Support, Customer Success, Product, and Sales, and you'll be the voice of the customer inside PolicyBook.

This role is ideal for someone who wants both the operational rigor of running a support function and the builder mindset of an enablement function — reducing time-to-value for new accounts while keeping response times, resolution times, and CSAT on target for existing ones.

What You'll Do

Onboarding & Adoption

• Design and run onboarding programs so new distributors and advisors reach their first "aha moment" quickly
• Build training materials, guides, and in-app guidance
• Reduce time-to-value for new accounts

Support Operations

• Handle tickets directly for a meaningful part of your week, especially early on
• Monitor key metrics: response time, resolution time, CSAT, ticket volume, backlog
• Ensure SLAs are met and identify/fix bottlenecks in support workflows
• Manage the support ticketing system/tools (e.g., Zendesk, Intercom, Freshdesk, Jira Service Management)

Content, Process & Quality

• Build and maintain support documentation, macros, knowledge bases, and self-serve resources
• Create and refine escalation procedures
• Maintain a resource library that scales with the customer base

Cross-Functional Liaison

• Sit between Product, Engineering, Sales, and Customer Success as the connective tissue for the customer experience
• Relay recurring issues, bug patterns, and feature gaps to Product/Engineering
• Translate product changes and releases into customer-facing communications

Metrics & Health

• Track adoption metrics (feature usage, activation rates, time-to-value)
• Identify at-risk accounts based on low engagement signals
• Report support and enablement metrics and trends to leadership

As the Function Scales

• Set support team goals and KPIs
• Choose and evaluate support tooling/vendors
• Build the repeatable systems, content, and tools that let future hires (support agents, CSMs) operate efficiently at scale
• Contribute to overall customer experience strategy, not just reactive ticket handling

What We're Looking For

• 3+ years in a customer support, customer success, or enablement role, ideally with some people-management or team-lead experience
• Comfort switching between hands-on ticket work and higher-leverage process/content building
• Experience with support tooling (Zendesk, Intercom, Freshdesk, Jira Service Management, or similar)
• Strong written communication skills — you'll be writing documentation, templates, and customer-facing comms
• A systems mindset: you look at a recurring problem and want to fix the process, not just the ticket
• Comfort working cross-functionally with Product and Engineering
• Bilingual French/English (PolicyBook operates in a bilingual Canadian market)
• Bonus: familiarity with the insurance or fintech/insurtech space, or with advisor/distributor-facing platforms

About PolicyBook

PolicyBook is a Montreal-based insurtech building an end-to-end insurance monitoring and sales enablement platform for the Canadian market, serving distributors and financial advisors.