Head of Professional Services & Customer Support

Rockstar is recruiting for a company that provides innovative software and services for urban forestry, GIS, and green infrastructure management. Their tools and data help cities, organizations, and consultants plan, preserve, and enhance the urban forest – creating greener, healthier communities. They are at an inflection point – scaling their customer support and professional services operations while fundamentally rethinking how they deliver support through AI, automation, and smarter processes. They are looking for a strategic, technically strong leader to own this transformation: someone who can manage a team through change, bring order to complexity, and build a support operation that’s dramatically more efficient and scalable than what exists today.

About the Company

They are at an inflection point – scaling their customer support and professional services operations while fundamentally rethinking how they deliver support through AI, automation, and smarter processes. They are looking for a strategic, technically strong leader to own this transformation: someone who can manage a team through change, bring order to complexity, and build a support operation that's dramatically more efficient and scalable than what exists today.

The Role

This is a hands-on leadership role. The Manager will manage a team of 6 (employees and contractors) across customer support and professional services, owning both the day-to-day execution and the strategic direction of how the company supports customers. Today, nearly 60% of the company's PS team's work requires direct database access – writing SQL queries, diagnosing data issues, performing migrations. While they are actively building UI tools to reduce this dependency, database expertise will remain critical for the foreseeable future. The right person brings real technical depth here, not just management experience.

The Manager will also inherit a large backlog with multiple stakeholder groups – internal CSMs, services teams, direct customers, and reseller partners – each with competing and often unspoken priorities. A core part of this role is turning that ambiguity into clear, actionable priorities for the team. The Manager needs the customer acumen to know when to go the extra mile, and the judgment to know when and how to draw the line.

Key Responsibilities

Team Leadership & Change Management

• Leads, coaches, and develops a team of 6 across support and professional services – running 1:1s, team meetings, and performance management.
• Drives the ongoing restructuring of the team for efficiency, including redefining roles, workflows, and day-to-day responsibilities. Supports team members through these transitions with clear communication and hands-on guidance.
• Builds systems for workload management, prioritization, and accountability that scale as the team evolves.
• Creates clarity from ambiguity : translates competing stakeholder needs into well-defined priorities and execution plans the team can act on.

Technical & Database Expertise

• Brings hands-on proficiency with SQL and relational databases (PostgreSQL preferred) to support, troubleshoot, and mentor the team on complex data issues.
• Understands how database-driven workflows underpin the company's support operations – from data imports and migrations to query-based investigations and bulk updates.
• Serves as a technical escalation point for Tier 3 issues involving database integrity, schema inconsistencies, API integrations, and GIS data workflows.
• Bridges the gap between the support team and Engineering by providing detailed technical context on bugs and systemic issues originating in the data layer.

AI Strategy & Automation

• This is not a nice-to-have. The company expects this person to fundamentally rethink how the team operates using AI and automation.
• Identifies and implements AI-driven solutions across the support function – automated customer responses, AI-assisted triage, knowledge base generation, proactive outreach, and self-service tools.
• Evaluates and deploys AI tools (e.g., Zendesk AI, ChatGPT/Claude integrations, custom workflows) to reduce manual effort and accelerate resolution times.
• Builds toward a future-state vision where AI handles a significant share of routine support volume, freeing the team for higher-value work.
• Stays current on AI capabilities relevant to support operations and continuously pushes the team to adopt smarter ways of working.

Stakeholder & Backlog Management

• Manages competing priorities across internal teams (Customer Success, Services, Sales) and external stakeholders (customers, reseller partners) with diplomacy and decisiveness.
• Owns the support and PS backlog : triages, prioritizes, and communicates status clearly to all stakeholders.
• Brings a service-minded attitude paired with the confidence to set boundaries, push back when needed, and communicate trade-offs effectively.
• Represents the voice of the customer in cross-functional discussions while balancing operational reality.

Process & Systems Optimization

• Owns and improves support processes including ticketing workflows, SLAs, escalation paths, and documentation.
• Optimizes the current multi-system environment (Zendesk + HubSpot) – Zendesk expertise is strongly preferred.
• Tracks and reports on key metrics (resolution times, CSAT, backlog health, team utilization) to drive data-informed decisions.
• Identifies inefficiencies and leads rapid-cycle improvements that make the team measurably more productive.

Customer Experience & Cross-Functional Collaboration

• Ensures timely, high-quality, empathetic customer support across all channels.
• Collaborates with Product, Engineering, Customer Success, and GIS Consulting to resolve complex issues and improve the end-to-end customer journey.
• Supports customer onboarding, training, and data workflows as needed, including GIS data preparation and review.

Qualifications

• 5+ years in technical support, solutions engineering, professional services, or application support.
• 2+ years managing or leading a team, with demonstrated experience coaching through organizational change.
• Proficient in SQL with hands-on experience working with relational databases (PostgreSQL, MySQL, or similar). Comfortable writing queries, diagnosing data issues, and mentoring others on database fundamentals.
• Strong AI literacy – actively uses AI tools in their work today and has a point of view on how AI transforms support operations. Experience implementing AI-driven workflows is a significant plus.
• Experience with Zendesk (strongly preferred) and familiarity with multi-system support environments (e.g., HubSpot, Jira).
• Excellent stakeholder management skills – able to navigate competing priorities, create clarity from ambiguity, and communicate trade-offs with both internal teams and external partners.
• Strong organizational and prioritization skills with a bias toward action and rapid iteration.
• Clear, confident communicator (English) who can translate technical complexity for non-technical audiences and deliver difficult messages with empathy and professionalism.
• Comfort working with GIS data formats and tools (Shapefiles, GeoJSON, QGIS) or strong willingness to learn.

Nice-to-Haves

• Experience with PostgreSQL/PostGIS or spatial database extensions.
• Background in GIS, urban forestry, arboriculture, or environmental science.
• Experience building or deploying AI chatbots, automated triage systems, or knowledge base automation.
• Familiarity with APIs, REST/JSON, and common web technologies.
• Scripting ability (Python, JavaScript, or Bash) for data processing or automation.
• Experience managing distributed/remote teams.
• Fluency in a second language (Spanish preferred).

Success Metrics

• Team Performance & Stability : Clear role accountability, successful team restructuring, strong retention, and measurable improvement in team capability and morale through the transition.
• Backlog & Resolution Efficiency : Reduced backlog, faster resolution times, SLA adherence, and fewer escalations through better process and prioritization.
• AI & Automation Impact : Measurable reduction in manual support effort through implemented AI tools and automated workflows within the first 6–12 months.
• Customer Satisfaction : High CSAT scores, positive stakeholder feedback, and a reputation for responsive, high-quality support.
• Process Maturity : Documented, repeatable processes across ticketing, escalation, and cross-functional handoffs with clear metrics and reporting.
• Stakeholder Confidence : Internal teams and external partners have visibility into priorities, status, and trade-offs – reducing friction and escalations.