GreenLight.ai

Head of Customer Success – Contingent Workforce

GreenLight.ai

full-time

Posted on:

Location Type: Remote

Location: United States

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Salary

💰 $115,000 - $160,000 per year

Job Level

Lead

About the role

  • Own a portfolio of strategic enterprise and marketplace accounts, acting as the primary executive contact for their contingent workforce programs.
  • Design and manage programs that cover onboarding, worker classification, compliance, time and expense, invoicing, and payments
  • Lead QBRs and other governance forums with program sponsors, procurement, HR, and other stakeholders, presenting performance, risks, and roadmap alignment.
  • Serve as the internal voice of the CW program and partner closely with Sales, Product, Operations, and Finance.
  • Own the implementation lifecycle for new enterprise customers, from discovery and design through configuration, testing, training, and go-live.
  • Build and manage project plans with clear milestones, owners, and risks; coordinate across client stakeholders (HR, procurement, legal, IT, security, finance) and internal teams.
  • Ensure solutions are configured to meet program objectives, compliance requirements, and user experience expectations for both client teams and workers.
  • Design and refine program structures, SLAs, escalation paths, and governance routines tailored to each key account.
  • Analyze program data (volumes, cycle times, issues, SLAs, CSAT/NPS, margins, etc.) to identify trends, risks, and opportunities.
  • Proactively propose process, policy, and product changes that improve quality, reduce friction, or unlock new value for clients and workers.
  • Use AI tools (for example, ChatGPT and other LLM-based copilots) in your daily work.

Requirements

  • At least 3 years working inside a large enterprise contingent workforce program, or as an embedded MSP/on-site leader supporting such a program.
  • Deep familiarity with VMS platforms (for example, Beeline, SAP Fieldglass)
  • MSP models and supplier ecosystems
  • Policies and realities of SOW, staff augmentation, independent contractor management, and worker classification
  • Proven track record in customer success, program management, or implementation for enterprise clients, ideally at a SaaS, HR tech, VMS, MSP, or related provider.
  • Strong project management skills: you can own complex implementations and ongoing programs end-to-end.
  • Experience designing and owning SOPs, playbooks, and governance routines for CW programs or enterprise accounts.
  • Demonstrated AI skills: Regular use of AI tools (such as ChatGPT or other LLMs) in your day-to-day work
  • Excellent written and verbal communication skills and strong executive presence.
  • A self-starter mindset: you take ownership, work through ambiguity, and build the playbook rather than waiting for one.
  • CCWP (Certified Contingent Workforce Professional) strongly preferred, or a clear plan and willingness to obtain it within your first year.
Benefits
  • medical, dental, and vision coverage
  • stock option eligibility
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
program managementimplementationdata analysisproject managementworker classificationcomplianceSOP designgovernance routinescustomer successAI tools
Soft Skills
communicationexecutive presenceself-starter mindsetownershipproblem-solvingcollaborationadaptabilityleadershipstrategic thinkingstakeholder management
Certifications
CCWP