Head of Customer Success, Support and Professional Services

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

📋 Description

• Take full ownership of the entire post-sale customer journey encompassing Customer Success, Technical Support, and Professional Services.

• Direct the onboarding, training, adoption, support, implementation, delivery of paid services, renewals, and expansion efforts.

• Oversee a personal portfolio that includes onboarding, adoption, renewal, and expansion initiatives.

• Manage the renewal process within HubSpot from the closed-won handoff through onboarding, growth, renewal quoting, and invoicing.

• Enhance net revenue retention, gross retention, churn prevention, upselling, cross-selling, and strategic account initiatives.

• Lead a multi-tiered technical support organization that includes self-service, Tier 1, Tier 2, and Tier 3 support.

• Monitor support metrics such as throughput, SLAs, backlog, and CSAT across Zendesk and HubSpot pipelines.

• Supervise bug triage, Engineering handoffs, prioritization, and customer follow-up processes.

• Spearhead implementation and training services, including application setup, configuration, customer training, data migrations, and paid technical services.

• Manage services scoping, quoting, delivery timelines, utilization, and invoicing coordination.

• Establish operational cadence and plan for team capacity.

• Directly supervise two Customer Success Managers and lead a five-member Support and Professional Services team.

• Take charge of hiring, coaching, performance management, retention, career development, and career path creation across all three functions.

• Represent the post-sale organization in leadership meetings and throughout company operations.

• Own the AI strategy for the post-sale department.

• Review recurring processes and identify opportunities for compression, automation, or elimination through AI.

• Design and implement workflows and AI-assisted standard operating procedures utilizing HubSpot, Zendesk, the support site, and internal customer data tools.

• Train the team and establish benchmarks for AI-assisted tasks.

• Evaluate the impact of automation through metrics such as hours reclaimed, tickets diverted, cycle time reductions, and capacity improvements.

• Manage the post-sale systems stack and address visibility gaps within CS, Support, and Professional Services.

• Develop and deliver a KPI scorecard that tracks retention, CSAT, resolution velocity, onboarding time-to-value, and service utilization.

• Stabilize support, enhance retention, unify post-sale operations, integrate AI automations, cultivate customer knowledge, establish a reliable scorecard, and fill crucial team positions during the first year.

⛳️ Requirements

• More than 5 years of post-sale leadership experience within a B2B SaaS organization.

• Proven track record of managing multiple functions or teams, including Customer Success, Support, and/or Services.

• Established experience in people management, covering hiring, coaching, performance management, retention, and managing other managers.

• Proven ownership of a renewal or net revenue retention metric.

• Experience operating a technical support function with tiers, SLAs, queues, and escalation paths.

• Familiarity with scoping, managing utilization, and margins for billable implementation or training activities.

• Proficiency with a modern CRM, with HubSpot being strongly preferred.

• Experience using Zendesk or a comparable ticketing system.

• Comfort with analyzing pipeline and queue data.

• Willingness to manage accounts, address escalations, and handle tickets in a small-company environment.

• Experience in designing and implementing AI workflows or automations.

• Ability to guide a team through AI adoption.

• Experience in vertical SaaS or GovTech, particularly selling to municipalities (preferred).

• Background with an international customer base and distributed teams, including those in the UK and Australia/New Zealand (preferred).

• Exposure to GIS/geospatial, urban forestry, arboriculture, or related fields, including SQL, QGIS/ArcGIS, or spatial data (preferred).

• Familiarity with public-sector procurement processes, purchase orders, Net-30 invoicing, and budget-cycle-driven renewals (preferred).

• Understanding of EOS/L10-style operating cadences (preferred).

🏝️ Benefits

• Company 401(k) with employer matching.

• Comprehensive health, dental, and vision coverage.

• Health Savings Account (HSA).

• Unlimited paid time off.

• Company-provided laptop.

• Other reimbursable expenses.

• Flexible working hours.

• Supportive and inclusive work culture.

• Opportunity to positively impact the environment and urban communities.

• Travel approximately 5-10% for key customers and industry conferences.