Head of Customer Success, Support and Professional Services
Rockstar is recruiting for a global leader in urban forestry software and services. Their SaaS platform helps cities, counties, states, universities, nonprofits, and tree care companies inventory, manage, and grow their urban forests, with more than 20 million trees under management across North America, the UK and Europe, and Australia/New Zealand. They pair market-leading software with professional services, GIS, and urban forestry consulting so customers succeed from first login to citywide canopy goals.
The Role
The company is hiring their first unified leader for the entire post-sale customer experience. You will own three teams (Customer Success, Technical Support, and Professional Services) and be accountable for everything that happens after a deal closes: onboarding and training, adoption, support, implementation and paid services delivery, renewals, and expansion.
This is a people-management role first. You will lead a team of seven (two Customer Success Managers as direct reports plus a five-person Support and Professional Services team) and you own hiring, coaching, performance, and career development across all three functions.
It is also a player-coach seat in the most literal sense: you will carry a working book of business of your own, deliberately smaller than a standard CSM load, because the fastest way to lead this org well is to learn their customers, renewal mechanics, and delivery processes firsthand, not from a dashboard. You will carry their net revenue retention and gross retention numbers, and you will also run the day-to-day engine, a tiered technical support operation, an implementation and training practice, and a renewal pipeline that serves both a public-sector and private-sector customer base. You will set strategy at the leadership table and get your hands dirty in the queue, the pipeline, and customer escalations in the same week.
What You'll Own
Customer Success and Retention
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Personal book of business: smaller than a typical CSM portfolio, that you own end-to-end: onboarding, adoption, renewal, and expansion. This is how you earn credibility with your team and stay close to the details of how their processes actually work.
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Renewal pipeline: end-to-end in HubSpot (from closed-won handoff and app delivery through onboarding, growth, renewal quoting, and invoicing), including the long procurement and PO cycles typical of municipal, university, and nonprofit customers.
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Retention targets: net revenue retention and gross retention targets; churn prevention driven by engagement and product-usage health signals, with an early-warning motion rather than renewal-time surprises.
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Expansion: upsell and cross-sell of modules and services plus quoting for all paid services work.
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Strategic accounts: strategic account and cohort programs that deepen relationships with their most important customers.
Technical Support
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Tiered support organization: Tier 1 general support, Tier 2 technical support (database configuration, data cleaning and migration, GIS tooling), and Tier 3 expert support working alongside Engineering, plus Tier 0 self-service through their knowledge base and AI assistant on the support site.
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Operational metrics: throughput, SLAs, backlog, and CSAT across the Zendesk and HubSpot ticket pipelines, including the intake-to-delivery flow for configuration and implementation tickets.
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Bug triage: bug triage and the handoff to Engineering: reproduction, prioritization, and closing the loop with customers.
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Team development: hiring, training, retention, and career-pathing for technical support staff, and the knowledge and change management that keeps expertise from walking out the door.
Professional Services
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Implementation and training practice: application setup and configuration, customer training delivery, data migrations and uploads, and a catalog of paid technical services.
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Delivery management: scoping, quoting, delivery timelines, and