Head of Customer Success, Support and Professional Services

🔥 0 minutes ago

🇨🇦 Canada – Remote

💵 $130k - $140k / year

⏰ Full Time

🔴 Lead

🏆 Customer Success

👻 Ghost score 0%

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Rockstar

WebsiteLinkedInAll Job Openings

1 - 10 employees

💼 Consulting

📣 Marketing

📦 Logistics

Consulting • Marketing • Logistics

Rockstar is a full-service recruitment company that leverages a blend of human expertise and artificial intelligence to help businesses hire better and faster at a lower cost. They offer a comprehensive recruitment service for less than $1,500 per role by providing access to a large talent database, fast and efficient candidate reviews, and human screening. Their proprietary AI enables the review of thousands of applications to quickly match candidates to job descriptions, while custom screening calls are conducted by recruiters in the US, UK, or Australia. Rockstar supports hiring across a wide range of professional roles, including sales, marketing, strategy, product, business operations, analytics, data science, software development, infrastructure, finance, and accounting. This flexible approach allows companies to meet strong candidates without long-term commitments, making it a cost-effective solution for teams of all sizes.

📋 Description

• Own the entire post-sale customer experience across Customer Success, Technical Support, and Professional Services • Lead onboarding, training, adoption, support, implementation, paid services delivery, renewals, and expansion • Manage a personal book of business covering onboarding, adoption, renewal, and expansion • Own the renewal pipeline in HubSpot from closed-won handoff through onboarding, growth, renewal quoting, and invoicing • Drive net revenue retention, gross retention, churn prevention, upsell, cross-sell, and strategic account programs • Lead a tiered technical support organization spanning self-service, Tier 1, Tier 2, and Tier 3 support • Manage support metrics including throughput, SLAs, backlog, and CSAT across Zendesk and HubSpot pipelines • Oversee bug triage, Engineering handoffs, prioritization, and customer follow-up • Lead implementation and training services, including application setup, configuration, customer training, data migrations, uploads, and paid technical services • Manage services scoping, quoting, delivery timelines, utilization, and invoicing coordination • Establish team operating cadence and capacity planning • Directly manage two Customer Success Managers and lead the five-person Support and Professional Services team • Own hiring, coaching, performance management, retention, career development, and career-path creation across all three functions • Represent the post-sale organization at the leadership table and in company operating cadence • Own the AI roadmap for the post-sale operation • Audit recurring processes and identify opportunities to compress, automate, or eliminate work with AI • Design and deploy agentic workflows and AI-assisted SOPs using HubSpot, Zendesk, the support site, and internal customer-data tools • Train the team and establish standards for AI-assisted work • Measure automation impact through hours returned, tickets deflected, cycle-time reductions, and capacity gains • Own the post-sale systems stack and close visibility gaps across CS, Support, and Professional Services • Create and report a KPI scorecard covering retention, CSAT, resolution velocity, onboarding time-to-value, and services utilization • Stabilize support, improve retention, unify post-sale operations, embed AI automations, build customer knowledge, establish a trusted scorecard, and fill key team roles during the first year

🎯 Requirements

• 5+ years in post-sale leadership at a B2B SaaS company • Experience managing multiple functions or managers, including Customer Success, Support, and/or Services • Proven people management experience, including hiring, coaching, performance management, retention, and managing managers • Experience owning a renewal or net revenue retention number • Experience running a technical support operation with tiers, SLAs, queues, and escalation paths • Experience scoping, managing utilization, and margin for billable implementation or training work • Fluency with a modern CRM; HubSpot strongly preferred • Experience with Zendesk or a similar ticketing platform • Comfort working with pipeline and queue data • Willingness to own accounts, handle escalations, and work tickets at small-company scale • Experience designing and shipping AI workflows or automations • Ability to bring a team along in AI adoption • Vertical SaaS or GovTech experience selling into municipalities (nice-to-have) • International customer-base and distributed-team experience, including UK and Australia/New Zealand (nice-to-have) • GIS/geospatial, urban forestry, arboriculture, or adjacent domain exposure, including SQL, QGIS/ArcGIS, or spatial data (nice-to-have) • Familiarity with public-sector procurement, purchase orders, Net-30 invoicing, and budget-cycle-driven renewals (nice-to-have) • Familiarity with EOS/L10-style operating cadences (nice-to-have)

🏖️ Benefits

• Company 401(k) with employer match • Comprehensive health, dental, and vision insurance • HSA • Unlimited paid time off • Laptop provided by the company • Other reimbursable expenses • Flexible work hours • Supportive and inclusive work culture • Opportunity to make a positive impact on the environment and urban communities • Travel roughly 5-10% for key customers and industry conferences