VP of Customer Success (Remote)

The company is a leading lien resolution company that specializes in streamlining the lien resolution process for personal injury law firms. We are looking for proactive, results-driven individuals to join our dynamic team.

We are seeking a VP of Customer Success to lead and scale the Customer Success organization as the company grows across verticals and new business lines. Reporting to the Chief Customer Officer, this role owns the full post-sale lifecycle: onboarding, adoption, ongoing engagement, retention, and expansion, along with the operating infrastructure that makes those outcomes repeatable.

You will lead two directors at hire, Director of Customer Success and Director of Onboarding & Enablement, and you will own the organizational design of the function as the book of business scales. This is a builder's seat with a mature-operator bar. The playbooks, health framework, coverage model, documentation, tech stack, and reporting cadence are yours to define and maintain, and you carry the numbers that come out of them.

You will partner closely with Lien Resolution Operations, Product, Finance, Sales, Marketing, and our vertical business lines to deliver a consistent, high-value customer experience across every segment we serve.

In your first year, you will focus on

• Work with the Director of Customer Success on the departmental operating model, including coverage, segmentation, escalation paths, and decision rights, so issues resolve at the right level without executive intervention.

• Stand up a single retention and expansion forecast, built with Finance, that the executive team can plan against.

• Work with the Director of Onboarding & Enablement to bring onboarding to a packaged, measurable approach across standard, pilot, and custom engagements, with time to value as a tracked KPI.

• Build the org plan for the function: capacity model, hiring sequence, role definitions, and a career path that develops team members into stronger operators.

• Take over the Voice of Customer and health-scoring rhythm that feeds Product prioritization with evidence rather than anecdote.

• Extend the Customer Success operating model beyond single-event injury to support additional business lines without duplicating infrastructure.

Requirements

Responsibilities

Function Leadership & Organizational Design

• Function Ownership: Own Customer Success strategy, execution, and outcomes across the full customer portfolio, translating company objectives into departmental targets and operating plans.

• Leading Leaders: Lead, coach, and develop a director-level team, holding a clear performance bar and building the next layer of leadership underneath it.

• Org Design & Capacity Planning: Own organizational design, coverage and segmentation models, workforce planning, employee development & growth pathing, and the hiring sequence for the function as the customer base scales.

• Operating Cadence: Define and run the operating rhythm of the department: goal setting, business reviews, forecast reviews, and reporting to the executive team.

Retention, Expansion & Portfolio Accountability

• Target Ownership: Own retention-related KPI’s (conversion and realization rates) and expansion targets in partnership with the Chief Customer Officer and Finance.

• Portfolio Health: Own overall portfolio health & modeling, including proactive identification of systemic retention risk and the cross-functional plans to mitigate it.

• Forecasting: Partner with Finance on renewal and expansion forecasting, with health and adoption data as the leading indicators behind the numbers.

• Commercial Partnership: Contribute customer evidence to pricing, packaging, and renewal terms, and partner with Sales & Partnerships on expansion and referral motions.

Onboarding & Time to Value

• Onboarding Standards: Own the onboarding experience through the Director of Onboarding & Enablement, including standard, pilot, and custom paths and the service commitments attached to each.

• Time to Value: Establish time to value and early-adoption measures as tracked outcomes of the function, not milestones tracked only during implementation.

• Handoff Quality: Own the quality of the sales-to-onboarding handoff jointly with sales & Partnerships, including scope, success criteria, and named owners on both sides.

Customer Experience & Engagement

• Engagement Model: Define the engagement model by segment, including touch cadence, business review standards, and the escalation path that supports it.

• Executive Sponsorship: Serve as executive sponsor and senior escalation point for strategic relationships, while ensuring routine escalations resolve at the lowest appropriate level.

• Voice of Customer: Own a structured Voice of Customer program that captures feedback systematically and converts it into prioritized recommendations for Product and leadership.

Process, Documentation & Enablement

• Documentation Ownership: Oversee the buildout and ongoing maintenance of playbooks, SOPs, and process documentation, treating them as living operating assets with named owners and a review cadence.

• Systems of Record: Own HubSpot configuration and reporting for the customer lifecycle, ensuring health, adoption, and lifecycle stage data is trustworthy enough to make decisions on.

• Enablement: Ensure the team is trained to a defined standard, with onboarding and ongoing enablement built into how the function runs.

Cross-Functional Partnership

• Product: Partner on adoption blockers, roadmap input, and portal utilization grounded in usage data.

• Lien Resolution Operations: Partner with Operations leadership so customer-facing commitments and operational execution stay aligned.

• Sales Partner on handoff quality, expansion signals, customer advocacy, testimonials, and referral generation.

• Marketing: Partner with Marketing and Product Marketing on go-to-market enablement and collateral, from internal rollout strategies all the way through case studies and customer advisory initiatives.

• Business Lines: Serve as the Customer Success partner to all verticals and emerging business lines, extending shared infrastructure rather than building parallel functions.

Qualifications

• 7+ years in customer success, account management, or client services within B2B SaaS or tech-enabled services, including 5+ years leading a customer-facing function through a growth stage.

• Demonstrated experience managing managers, including at least one director-level report, and managing up to the executive or board level.

• Track record as the named owner of retention and expansion targets, with the reporting and forecasting to support them.

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

• Experience standing up or scaling an onboarding, implementation or professional services function as part of the customer lifecycle.

• Proven ability to operate without an existing playbook, set direction independently, and bring forward recommendations with a clear point of view.

• Strong data fluency, including business analysis from reports and comfort using AI tools to support analysis, workflow design, and customer communications.

• Proficiency with CRM systems (e.g., HubSpot, Salesforce) and reporting tools.

• Bachelor's degree required. Focus in business, law, or a related field is preferred.

• Experience in legal services, personal injury, or litigation-adjacent technology is strongly preferred.

• Ability to travel up to 40%.

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

Pay Disclosure: The total base salary range for this role is $151,000 - $205,000 annually, with an opportunity for a discretionary bonus. Final compensation will be determined based on skills and experience.

Work Authorization: Applicants must be authorized to work in the United States without the need for employer-sponsored visa support now or in the future.