VP, Customer Experience

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take charge of retention and expansion revenue across the customer base: GRR, NRR, renewal forecasting, and the expansion pipeline, with reports submitted to leadership and the board.

• Oversee the customer experience standards for the entire organization: activation milestones, health scoring, and playbooks that are applicable to every account, including those served by your teams in the enterprise segment.

• Ensure customer success and retention: comprehend the factors influencing each renewal and every loss, and develop engagement and adoption strategies that keep contractors profitable.

• Transform the product roadmap into customer value: as new AI-driven products are released, create strategies that align each launch with the customers it will benefit, resulting in subsequent expansion revenue.

• Define what "activated" signifies for every Encircle product: establish activation thresholds, staged milestones with deadlines and exit criteria, tracked in ChurnZero and Snowflake, and accessible across the organization.

• Develop a tiered, signal-driven account management model: determine which accounts receive in-depth quarterly business reviews, which are monitored through automated health assessments and signal-triggered outreach, along with the SLAs governing both.

• Implement formula discipline across all three teams: create documented playbooks, published benchmarks, and Snowflake-supported dashboards, ensuring every team is aligned with the established benchmarks.

• Collaborate with Revenue Operations on continuous reporting, ensuring team and individual performance against benchmarks is always visible to your teams, leadership, and the broader organization.

• Co-manage the product-led growth strategy with Marketing: your organization specifies the adoption outcomes and content requirements; Marketing is responsible for content production, the Learning Hub platform, and search optimization.

• Integrate training and Learning Hub resources into the product and onboarding milestones, delivering them at the moment of need.

• Spearhead AI adoption across the Customer Experience organization, incorporating AI agents and AI-assisted workflows into onboarding, account management, and support operations.

• Leverage AI to synthesize qualitative customer feedback and usage patterns into insights that inform product and go-to-market strategies.

• Treat self-service activation and support deflection as critical metrics, aiming to expand coverage without proportionately increasing headcount.

• Lead, develop, and nurture the three managers and their teams, cultivating a high-performance culture centered around the client experience for which Encircle is recognized.

• Establish and maintain executive relationships with our most strategic accounts, serving as an escalation point and trusted advisor.

• Foster customer advocacy: reference customers, case studies, reviews, and community involvement.

• Collaborate with Sales on seamless handoffs, expansion opportunities, and account strategies for key and at-risk accounts.

• Work with Product to close the feedback loop between customer insights and the product roadmap, ensuring the voice of the customer is prioritized.

• Partner with Finance and HR on compensation structuring and capacity planning for your teams.

⛳️ Requirements

• Over 10 years of experience in customer success, customer experience, or related post-sale roles in B2B SaaS, including at least 3 to 5 years in senior leadership positions (Director, VP, or equivalent) managing teams.

• Direct responsibility for improving NRR and GRR, with specific results to discuss.

• Proven experience in building and scaling post-sale teams: you’ve successfully hired, developed, and led high-performing managers, not just individual contributors.

• Experience operating multi-segment models: balancing scaled, signal-driven SMB coverage alongside a higher-touch approach for enterprise and mid-market clients.

• A strong operational and analytical mindset: you manage through metrics, develop repeatable processes, and hold teams accountable to published benchmarks.

• Practical experience with customer success platforms; familiarity with ChurnZero and Salesforce is a strong advantage, and comfort with Snowflake-backed reporting is beneficial.

• Experience integrating AI agents into customer success or support operations, and utilizing AI to convert qualitative feedback and usage data into actionable decisions.

• Exceptional executive communication skills: you can establish trust with a VP of Claims at a regional insurer just as easily as with a restoration company owner in the field.

• A scaling mindset: you prioritize product, content, automation, and AI before requesting additional headcount.

• Experience in property insurance, restoration, insurtech, or field services is a significant asset.

🏝️ Benefits

• Balance: flexible working hours, self-managed vacation, and trust to manage your own time.

• Remote-first: work in your most productive environment, with access to our collaboration hub in Kitchener.

• Growth-oriented: we support your learning and career development.

• Well-being: we prioritize the complete individual, both inside and outside of work.