Remotehey

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.

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.

Customer and program ownership

• 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.

Implementation and delivery

• 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.

Program design and continuous improvement

• 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.

AI-enabled customer success

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.

Systems, SOPs, and team leadership

• 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.

Non-negotiables

• 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, Vndly) and 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 including 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.

Credentials and domain

• 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 have

• 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.

• You’ll bring your inside contingent workforce program experience to a company building the infrastructure that supports those programs.
• You’ll shape how customer success and program management are done at GreenLight and how some of the world’s most interesting companies run their contingent workforce.
• You’ll work in an AI-first environment, with the expectation and support to use AI as leverage in your day-to-day work.
• You’ll be part of a small, senior, high-ownership team where your relationships and decisions directly impact company outcomes.
• You’ll have access to a generous benefits package, including medical, dental, and vision coverage, plus stock option eligibility.
•  You're ambitious and you want to be part of a world-class team building a category-defining company.