Head of Professional Services – Customer Support

This is a fully remote position, open to applicants in Canada, +4 more states.

📋 Description

• Oversees, mentors, and cultivates a team of 6 in support and professional services, conducting 1:1s, team meetings, and performance evaluations.

• Leads the continuous restructuring of the team for enhanced efficiency, which includes redefining roles, workflows, and daily responsibilities. Provides support to team members during these transitions through clear communication and proactive guidance.

• Develops systems for managing workloads, prioritization, and accountability that can scale as the team develops.

• Clarifies ambiguity by translating conflicting stakeholder needs into well-defined priorities and actionable execution plans for the team.

• Possesses hands-on expertise in SQL and relational databases (preferably PostgreSQL) to assist, troubleshoot, and mentor the team on intricate data challenges.

• Comprehends how database-driven workflows support the company's operations—ranging from data imports and migrations to query-based investigations and bulk updates.

• Acts as a technical escalation point for Tier 3 issues related to database integrity, schema inconsistencies, API integrations, and GIS data workflows.

• Serves as a liaison between the support team and Engineering by providing in-depth technical context on bugs and systemic problems stemming from the data layer.

• This role is essential; the company anticipates this individual to fundamentally rethink the team's operations through the use of AI and automation.

• Identifies and implements AI-driven solutions throughout the support function, including automated customer responses, AI-assisted triage, knowledge base creation, proactive outreach, and self-service tools.

• Assesses and deploys AI tools (e.g., Zendesk AI, ChatGPT/Claude integrations, custom workflows) to minimize manual tasks and expedite resolution times.

• Works towards a future vision where AI manages a significant portion of routine support volume, enabling the team to focus on higher-value tasks.

• Remains updated on AI capabilities pertinent to support operations and consistently encourages the team to adopt more efficient working methods.

• Manages competing priorities across internal teams (Customer Success, Services, Sales) and external stakeholders (customers, reseller partners) with tact and decisiveness.

• Takes ownership of the support and professional services backlog: triages, prioritizes, and communicates status clearly to all stakeholders.

• Exhibits a service-oriented mindset while having the confidence to set boundaries, respectfully push back when necessary, and communicate trade-offs effectively.

• Represents the customer perspective in cross-functional discussions while balancing operational realities.

• Owns and enhances support processes, including ticketing workflows, SLAs, escalation procedures, and documentation.

• Optimizes the current multi-system environment (Zendesk + HubSpot), with a strong preference for Zendesk expertise.

• Monitors and reports on key metrics (resolution times, CSAT, backlog health, team utilization) to facilitate data-driven decisions.

• Identifies inefficiencies and leads rapid-cycle improvements that significantly boost team productivity.

• Ensures timely, high-quality, and empathetic customer support across all channels.

• Collaborates closely with Product, Engineering, Customer Success, and GIS Consulting to resolve complex issues and enhance the end-to-end customer experience.

• Assists with customer onboarding, training, and data workflows as required, including GIS data preparation and review.

⛳️ Requirements

• A minimum of 5 years in technical support, solutions engineering, professional services, or application support.

• At least 2 years of experience managing or leading a team, with proven experience in coaching through organizational change.

• Proficient in SQL with practical experience working with relational databases (PostgreSQL, MySQL, or similar). Comfortable writing queries, diagnosing data issues, and mentoring others on database fundamentals.

• Strong knowledge of AI – actively utilizes AI tools in their current work and holds a viewpoint on how AI transforms support operations. Experience in implementing AI-driven workflows is a notable advantage.

• Familiarity with Zendesk (strongly preferred) and knowledge of multi-system support environments (e.g., HubSpot, Jira).

• Excellent stakeholder management abilities – skilled at navigating competing priorities, creating clarity from ambiguity, and communicating trade-offs with both internal teams and external partners.

• Strong organizational and prioritization skills with a proactive approach to action and rapid iteration.

• Clear and confident communicator (English) who can simplify technical complexities for non-technical audiences and convey challenging messages with empathy and professionalism.

• Comfortable working with GIS data formats and tools (Shapefiles, GeoJSON, QGIS) or a strong willingness to learn.

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance.

• Generous paid time off and flexible work arrangements.

• Opportunities for professional development and growth.

• Collaborative and inclusive company culture.