Head of Customer Success - Contingent Workforce

GreenLight Workforce Solutions Inc

12d

About The Position

About GreenLight.ai GreenLight.ai builds the infrastructure behind modern independent work. We help global enterprises and talent marketplaces compliantly onboard, classify, and pay contractors in 40+ countries. We’re a small, lean, profitable team with multiple years of strong year-over-year growth, working with leading brands in AI, retail, marketplaces, and media/technology. GreenLight.ai is an API-first enterprise platform focused on process automation, AI, digitizing workflows, and building intuitive experiences for clients and workers. We turn complex, high-risk workflows—worker classification, global onboarding, compliance, payments—into simple, reliable products. We offer a generous benefits package, including medical, dental, and vision coverage, as well as stock option eligibility. Role Overview We’re looking for a Head of Customer Success who has direct, inside experience running or supporting a contingent workforce (CW) program at a large enterprise. You’ve sat in the seat of: A CW program manager or director An MSP on-site or program lead Or a similar role inside a large enterprise where you owned or heavily supported the contingent workforce program You understand how VMS, MSP, HR, and procurement work day-to-day, what program sponsors and hiring managers actually care about, and where implementations and programs really fail or succeed. At GreenLight, you will own: Account management and executive relationships Implementation delivery and program rollout Ongoing customer success and satisfaction Program design and continuous improvement for complex, multi-country clients You should be a self-starter who can build and run Customer Success in a lean, high-ownership environment, comfortable translating between enterprise program needs and our platform and services. You should be technical enough to work with a platform/API product, partner closely with product and engineering, and highly AI-literate so you use AI tools every day to analyze, communicate, and scale your work. This role is both strategic and hands-on: you’ll be the face of GreenLight for key accounts and the architect of the systems, SOPs, and playbooks that make our service world-class.

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.
Titles might include CW program manager/director, MSP program manager, VMS program lead, or similar.
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.
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.

Nice To Haves

Experience on both sides of the ecosystem: Inside an enterprise CW program, and At a vendor (VMS, MSP, HR tech, SaaS)
Exposure to API-first or platform products and working closely with product and engineering.
Experience with global programs spanning multiple regions and regulatory environments.

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.