VP of Customer Success

This is a fully remote position, open to applicants in Kentucky.

📋 Description

• Lead and expand the Customer Success organization across various verticals and new business lines.

• Take ownership of the entire post-sale lifecycle, which includes onboarding, adoption, engagement, retention, and expansion.

• Develop and maintain playbooks, health frameworks, coverage models, documentation, technology stack, and reporting cadence.

• Supervise the Director of Customer Success and the Director of Onboarding & Enablement.

• Manage organizational design, capacity planning, hiring sequences, role definitions, and career pathways.

• Collaborate with Finance to establish retention and expansion forecasting.

• Create quantifiable onboarding paths and monitor time to value as a key performance indicator (KPI).

• Oversee Voice of Customer and health-scoring initiatives to guide Product prioritization.

• Define customer engagement frameworks, touch cadence, business review standards, and escalation procedures.

• Act as the executive sponsor and primary escalation contact for strategic customer relationships.

• Manage HubSpot configuration and customer lifecycle reporting.

• Collaborate with Operations, Product, Finance, Sales, Marketing, and business lines to enhance customer experience, adoption, expansion, and enablement.

• Extend the Customer Success operational model to additional business lines without duplicating existing infrastructure.

⛳️ Requirements

• 7+ years of experience in customer success, account management, or client services within B2B SaaS or technology-enabled services.

• 5+ years of experience leading a customer-facing function through a growth phase.

• Proven experience managing managers, including at least one director-level report.

• Experience in managing relationships with executive or board-level stakeholders.

• Demonstrated success in owning retention and expansion targets, along with relevant reporting and forecasting.

• Experience in building or significantly rebuilding a Customer Success operating model, encompassing segmentation, coverage, health scoring, playbooks, business review standards, escalation paths, and documentation.

• Experience establishing or scaling an onboarding, implementation, or professional services function.

• Capability to operate without a pre-existing playbook and independently set direction.

• Strong data fluency, including business analysis from reports and familiarity with AI tools.

• Proficiency in CRM systems such as HubSpot or Salesforce and associated reporting tools.

• Bachelor's degree is required.

• Experience in legal services, personal injury, or technology related to litigation is highly preferred.

• Willingness to travel up to 40%.

• Applicants must be authorized to work in the United States without employer-sponsored visa support, now or in the future.

🏝️ Benefits

• Private Health Care Plan (Medical, Dental & Vision).

• Company HSA contributions for HDHP participants.

• Flexible Spending Accounts (Health & Dependent Care).

• Company-Paid Short-Term Disability Coverage.

• Voluntary Long-Term Disability, Life, AD&D, and Supplemental Coverage Options.

• 401(k) Plan with Company Match.

• Paid Time Off (Vacation, Sick Time & Select Holidays).

• Paid Parental Leave.

• Discretionary bonus opportunity.

• Remote work arrangement.