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
• 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 or experience will be disqualified.