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 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. 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. 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. Expansion: upsell and cross-sell of modules and services plus quoting for all paid services work. Strategic accounts: strategic account and cohort programs that deepen relationships with their most important customers. Technical Support 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. 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. Bug triage: bug triage and the handoff to Engineering: reproduction, prioritization, and closing the loop with customers. 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 Implementation and training practice: application setup and configuration, customer training delivery, data migrations and uploads, and a catalog of paid technical services. Delivery management: scoping, quoting, delivery timelines, and utilization for billable work, with clean coordination into invoicing. Operating cadence: team operating cadence (daily standups, weekly task planning) and capacity planning. Leadership and People Management Direct management: direct management of two Customer Success Managers and leadership of the five-person Support and Professional Services team: goal-setting, coaching, performance management, and development plans. Hiring and retention: hiring and retention across all three functions, including building tier-to-tier and IC-to-manager career paths so knowledge and talent stay in the building. Executive representation: representing the post-sale organization at the leadership table and in the company operating cadence. AI and Automation AI roadmap: the AI roadmap for the entire post-sale operation. They already run some AI-assisted workflows in production (customer meeting follow-up, for example). You'll treat those as the starting point, not the finish line. Process audit: a systematic audit of every recurring process across CS, Support, and PS (renewal prep, onboarding, ticket triage, quoting, data migrations, account health monitoring) to identify where AI can compress, automate, or eliminate work. Building the automations: designing agentic workflows and AI-assisted SOPs around their actual systems (HubSpot, Zendesk, their support site, internal customer-data tools) and getting them into daily production use. Team enablement: raising the AI fluency of the whole team (training, standards, and expectations) so AI-assisted work becomes the default operating mode and they grow the customer base without growing headcount linearly. Measuring impact: hours returned, tickets deflected, cycle times cut, capacity created, reported alongside the retention and support KPIs, and fed into staffing and planning decisions. Systems and Data Systems stack: the post-sale systems stack (HubSpot pipelines, Zendesk, and the support site), including closing cross-team visibility gaps so CS, Support, and PS work from one view of the customer. KPI scorecard: a post-sale KPI scorecard (retention, CSAT, resolution velocity, onboarding time-to-value, services utilization) reported into the leadership operating cadence. Your First Year: What Success Looks Like Support stabilized: the ticket backlog is worked down to near zero, throughput exceeds inbound, SLAs are consistently met, and the team is staffed and retained. Retention on track: net revenue retention holds above 100% with improving gross retention, backed by a health-signal model that flags at-risk accounts months before renewal. Unified post-sale motion: the three teams operate as one post-sale motion: shared visibility across HubSpot and Zendesk, clean handoffs from Sales through onboarding to steady-state, and no customer falling between functions. AI embedded: several new automations in daily production use across CS, Support, and PS, a team that reaches for AI by default, and measurable capacity gains you can show the leadership team. Firsthand customer knowledge: your own book of business is healthy, renewed, and expanding, and what you learned from it has sharpened the playbooks your team runs. Trusted scorecard: a trusted KPI scorecard exists and drives decisions at the leadership level. Team built out: key open roles are filled, tier-to-tier career paths exist, and knowledge is documented rather than tribal. What You Bring Must-Haves Post-sale leadership experience: 5+ years in post-sale leadership at a B2B SaaS company, including experience managing multiple functions or managers (CS + support and/or services). People management: proven people management: you have hired, coached, performance-managed, and retained teams, including managing managers. Retention ownership: you have owned a renewal or NRR number and can talk specifically about how you moved it. Support operations experience: you have run a technical support operation (tiers, SLAs, queues, escalation paths) not just an account management team. Services delivery experience: scoping, utilization, and margin on billable implementation or training work. Systems fluency: fluency with a modern CRM (HubSpot strongly preferred) and a ticketing platform (Zendesk or similar); comfortable living in pipeline and queue data. Player-coach temperament: you build systems and process, and you're equally willing to own accounts, jump into escalations, and work tickets at small-company scale. AI builder mindset: you build with AI, not just use it: you can point to workflows or automations you designed and shipped for yourself or your team, and to how you brought a team along with you. Nice-to-Haves Vertical SaaS or GovTech experience selling into municipalities. International experience: with international customer bases (UK, Australia/NZ) and distributed teams. Domain exposure: GIS/geospatial, urban forestry, arboriculture, or adjacent domain exposure (SQL, QGIS/ArcGIS, spatial data). Public-sector familiarity: procurement, purchase orders, Net-30 invoicing, and budget-cycle-driven renewals. Operating cadence familiarity: with EOS/L10-style operating cadences. Compensation and Benefits Location: Remote. Travel roughly 5-10% for key customers and industry conferences. Compensation: $130,000-140,000 base commensurate with experience; OTE: $145,000-160,000 (base + variable tied to retention/expansion). Benefits: company 401(k) with employer match, comprehensive health, dental, and vision insurance, HSA, and unlimited paid time off. Equipment: laptop provided by the company as well as other reimbursable expenses. Culture: flexible work hours, a supportive and inclusive work culture, and the opportunity to make a positive impact on the environment and urban communities. Pay schedule: they pay every other week through direct deposit. The company is an equal opportunity employer. They celebrate diversity and are committed to creating an inclusive environment for all employees.