VP, Customer Experience

VP, Customer Experience

🌎 Remote (Canada) | Hybrid option available in Kitchener, ON
🧑‍💼 Reports to: CEO
🏢 About Encircle

Encircle is leading the $1.6 trillion property insurance industry out of the dark ages of pen-and-paper processes. Our easy-to-use software platform helps thousands of restoration contractors and insurance professionals around the world document losses, generate scopes and process claims faster.

We're a remote-first company with a collaboration hub in downtown Kitchener, and we're growing.
📋 About the Role

Encircle's brand is built on the client experience. Our customers love Encircle for our people, and this role exists to keep that true as we grow: taking an experience our team already delivers exceptionally well and building the systems that bring it to thousands more customers. As VP, Customer Experience, you'll own the full post-sale journey for our customers, from first onboarding through renewal and expansion, and the numbers that prove the experience is working: gross revenue retention, net revenue retention, churn and expansion revenue.

You'll lead through three managers and their teams: Onboarding & Activation, who own new customer onboarding, activation on every new product purchase and re-adoption when an account shows churn risk; Account Growth, who carry the lifecycle, renewals and growth of large signal-driven books; and Support, who keep customers unblocked with fast, technical help. Your job is to build the operating system that connects them: defined activation milestones, tiered engagement models, published benchmarks and always-on reporting, so customer outcomes are repeatable and measurable rather than dependent on individual effort.

This is a leader who combines operational discipline with genuine customer empathy. You're equally comfortable in an executive business review and rolling up your sleeves to fix a broken onboarding flow, and you believe the best customer experience organizations scale through product, content and AI before they scale through headcount.
🔧 What You'll Be Doing

Own the customer outcomes

- Own retention and expansion revenue across the customer base: GRR, NRR, the renewal forecast and the expansion pipeline, reported to leadership and the board

- Own the customer experience standards for the whole company: activation milestones, health scoring and playbooks apply to every account, including enterprise accounts served by your teams

- Keep customers successful and with us: understand the drivers behind every renewal and every loss, and build the engagement and adoption depth that keep contractors profitable

- Turn the product roadmap into customer value: as new AI-driven products ship, build the motion that matches each launch to the customers it will help, and the expansion revenue follows

Build the operating system

- Own what "activated" means for every Encircle product: activation thresholds, staged milestones with dates and exit criteria, instrumented in ChurnZero and Snowflake and visible across the business

- Design the tiered, signal-driven account management model: which accounts get true quarterly business reviews, which run on automated health monitoring plus signal-triggered outreach, and the SLAs that govern both

- Run the formula discipline across all three teams: documented playbooks, published benchmarks and Snowflake-backed dashboards, with every team managed to benchmark

- Partner with Revenue Operations on always-on reporting, so team and individual performance against benchmarks is visible to your teams, to leadership and to the wider business at all times

Scale through product, content and AI

- Co-own the product-led growth motion with Marketing: your organization defines the adoption outcomes and content needs; Marketing owns content production, the Learning Hub platform and search optimization

- Embed training and Learning Hub resources into the product and into onboarding milestones, at the moment of need

- Le