VP, Customer Experience

VP, Customer Experience

Remote (Canada) | Hybrid option available in Kitchener, ON

Reports to: CEO

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
• 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
• Partner with Sales on clean handoffs, expansion opportunities and account strategy for key and at-risk accounts
• Partner with Product to close the loop between customer insight and roadmap, so the voice of the customer is heard and prioritized
• Partner with Finance and HR on compensation design and capacity planning for your teams

Key Metrics You'll Own

• Gross revenue retention (GRR)
• Net revenue retention (NRR)
• Expansion revenue and the pipeline that feeds it
• Activation rate and time-to-activation
• Self-serve activation rate and support deflection
• Customer health and CSAT

What Success Looks Like in Year One

• GRR and NRR ahead of target and trending upward
• Time-to-activation improving quarter over quarter across every product
• Seamless customer journey from onboarding through account management and support, with a named owner at every stage
• Every team performing to published benchmarks, visible in live dashboards
• Always-on enablement scaling: Learning Hub embedded in-product and in onboarding milestones, with self-serve activation and deflection trending upward
• A team culture your customers can feel: the reviews still say they love Encircle for our people

What You'll Bring

• 10+ years in customer success, customer experience or related post-sale functions in B2B SaaS, with at least 3 to 5 years in senior leadership (Director, VP or equivalent) leading managers
• Direct ownership of NRR and GRR improvement, with specific results you can speak to
• Experience building and scaling post-sale teams: you've hired, developed and led high-performing managers, not just ICs
• Experience operating multi-segment models: scaled, signal-driven SMB coverage alongside higher-touch enterprise and mid-market
• A strong operational and analytical mindset: you manage by metrics, build repeatable processes and hold teams to published benchmarks
• Hands-on experience with customer success platforms; ChurnZero and Salesforce experience is a strong asset, and comfort with Snowflake-backed reporting is a plus
• Experience integrating AI agents into a customer success or support operation, and using AI to turn qualitative feedback and usage data into decisions
• Excellent executive communication: you can build trust with a VP of Claims at a regional insurer as readily as with a restoration company owner in the field
• A scale mindset: you reach for product, content, automation and AI before asking for headcount
• Experience in property insurance, restoration, insurtech or field services is a meaningful asset

Nice to Have

• Experience leading a post-sale organization through a significant product expansion or market shift
• Experience scaling through a high-growth phase, including executive-level reporting on retention metrics
• Experience with revenue operations tooling and forecasting discipline

Why Encircle?

We VALUE our people:

• Balance: flexible hours, self-managed vacation and trust to manage your time
• Remote-first: work where you're most productive, with access to our collaboration hub in Kitchener
• Growth-oriented: we support your learning and career development
• Well-being: we care about the full human, inside and outside of work

Encircle is an equal opportunity employer committed to building a diverse and inclusive team. We encourage all qualified candidates to apply and will work with applicants to accommodate accessibility needs throughout the hiring process.

A note on your application: we use AI every day at Encircle and we expect you will too. What we're looking for in your application is you: your real experience, your own words and an accurate picture of what you've built. Applications that misrepresent skills