Head of Customer Success

We are looking for a dynamic Head of Customer Success to lead our CS function, owning net retention and driving lifetime value (LTV) across our portfolio while turning clients into raving promoters. In this role, you will oversee a small but rapidly growing team of CSMs at the Treeline level, while developing playbooks, training, and management strategies for CS/CX teams within our PortCos. You'll play a key part in integrating new acquisitions' CS operations seamlessly into our ecosystem, ensuring fanatical service, upsells, and retention to support our organic growth targets. You'll thrive in our startup culture by building an awesome company from the ground up, putting in the effort to ensure every client outcome is exceptional, and creatively solving challenges in a multi-entity environment.

• Net Retention Ownership: Drive net revenue retention at Treeline through upsell, expansion, renewal, and onboarding strategies; monitor metrics like LTV, ACV, churn signals, and utilization to identify risks and opportunities.
• Playbook and Training Development: Create standardized playbooks, training programs, and best practices for CS/CX processes, focusing on fanatical customer service, strategic advisory, and automation to elevate teams and compress time-to-value for new customers and activations (TTV).
• Team Leadership and Recruiting: Hire, mentor, and manage CSMs at Treeline; recruit and oversee dotted-line CS/CX teams across PortCos, establishing rhythms for reviews, trainings, and performance to scale with growth.
• PortCo Integration: Lead the integration of new acquisitions' CS operations into the Treeline portfolio, collaborating with ops and product teams to standardize workflows, pull customer feedback into roadmaps, and ensure seamless handoffs without quality slips.
• Customer Advocacy: Serve as the "voice of the customer" for product and service roadmaps; turn clients into promoters through case studies, referrals, testimonials, reviews, and gifting campaigns.
• Cross-Functional Collaboration: Partner with sales, marketing, onboarding, and service delivery teams to align on customer journeys, mitigate manual risks, and maximize ACV/LTV; use AI tools to scan interactions for churn/upsell insights.
• Metrics and Innovation: Track key metrics like expansion lift and retention rates; experiment with creative approaches, including AI-driven workflows and self-serve portals, to do more with less in a startup setting.

• Experience: 3+ years in CS/CX leadership, ideally in SaaS/IT services with M&A integration exposure; proven success scaling teams in multi-entity or startup environments while driving net retention >100%.
• Retention Expertise: Strong track record in upsell/expansion/renewal strategies, onboarding optimization, and turning customers into advocates; familiar with tools like HubSpot, Gong, and AI for sentiment analysis.
• Integration and Scaling Skills: Experience developing playbooks and training for distributed teams; adept at post-acquisition integrations to preserve local trust while centralizing standards.
• Travel: Willingness to travel up to 30% of the time, including 1-2 weeks/month at HQ or PortCos for integrations.
• Communication: Exceptional verbal and written skills; you can simplify complex technical concepts for non-technical buyers.‍
• Startup Mindset: You thrive in a fast-paced environment where the playbook is still being written and are comfortable with ambiguity.

• Competitive compensation
• Healthcare + Vision + Dental benefits
• Hybrid work environment
• Flexible time-off policy
• Transparent, flat culture