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 organisations 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 optimisation

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

Lead AI adoption across the Customer Experience organization, building AI agents and AI-assisted workflows into onboarding, account management and support operations

Use AI to synthesize qualitative customer feedback and usage patterns into insights that guide product and go-to-market decisions

Treat self-serve activation and support deflection as first-class metrics, and grow coverage without growing headcount proportionally

Lead the organization

Lead, develop and grow the three managers and their teams, building a high-performance culture anchored to the client experience Encircle is known for

Build and maintain executive relationships with our most strategic accounts, acting as escalation point and trusted advisor

Drive customer advocacy: reference customers, case studies, reviews and community participation

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