GreenLight.ai · 4 days ago
Head of Customer Success - Contingent Workforce
United States
Full-time
Remote
Lead/Staff, Director/Executive
$115K/yr - $160K/yr
3+ years expGreenLight.ai builds the infrastructure behind modern independent work, helping global enterprises compliantly onboard and manage contractors. The Head of Customer Success will own customer relationships, lead program implementations, and drive continuous improvement for contingent workforce programs.
Artificial Intelligence (AI)Human ResourcesInsuranceSoftware
Responsibilities
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 to: Draft and refine client communications, decks, and program documentation; Summarize complex issues such as tickets, escalations, policies, and contracts; Identify patterns in support tickets, implementation issues, and program metrics
Help define and shape AI-enabled customer success workflows, including: Standardized responses and knowledge base content; Templates for implementation and program design; Internal copilots for customer success and implementation/operations teams
Partner with Product to provide structured feedback and examples that can be used to train and improve GreenLight’s AI-driven features
Design and own SOPs, playbooks, and runbooks for customer success, implementations, and account governance
Establish customer success processes and tooling (for example, CRM, ticketing, health scoring, QBR templates) that scale with growth
Over time, hire, manage, and mentor a small customer success/implementation team and help build the function as we grow
Qualification
Required
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
Comfort experimenting with AI-driven workflows, automation, and content
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
Preferred
CCWP (Certified Contingent Workforce Professional) strongly preferred, or a clear plan and willingness to obtain it within your first year
Deep understanding of contingent workforce best practices, governance, and metrics at large enterprises
Benefits
Medical
Dental
Vision coverage
Stock option eligibility
Company
GreenLight.ai
GreenLight.ai is an AI-powered platform that helps businesses compliantly hire, manage, and pay freelancers and contract workers.
11-50 employees
Funding
Current Stage
Early StageTotal Funding
unknown2020-03-31Pre Seed
2020-02-05Pre Seed
2018-11-21Pre Seed
Company data provided by crunchbase