The OpportunityWorkWhile is building the operating infrastructure for the modern hourly workforce. As we scale our enterprise partnerships, the operational complexity of serving our largest customers - across integrations, billing, and reconciliation - has become one of the most important problems to solve. This role sits at the center of it.
This is a high-impact, cross-functional role at the intersection of operations, data science, product, and finance. You'll work across all of these functions with real authority - partnering with Product and Engineering on systems reliability, with Finance on invoicing accuracy and AR, and with GTM to ensure new enterprise customers are set up for clean execution from day one.
You'll own the end-to-end integrity of WorkWhile's most complex operational workflows - rebuilding reconciliation processes, tightening data quality standards, and designing the commercial and policy controls that make enterprise growth sustainable and profitable. You'll lead a small team executing these workflows day-to-day, and you'll be responsible for identifying automation opportunities, translating them into clear product requirements, and advocating for their prioritization with Engineering - raising the ceiling on what the function can do without growing headcount linearly.
This role is for someone who is deeply analytical, commercially sharp, and energized by turning messy, manual processes into clean, scalable systems.
What You'll OwnIntegration Architecture & Product Partnership- Act as the operational owner and business driver for all Vendor Management System (VMS) integrations - holding Product and Engineering accountable for reliability, scalability, and roadmap prioritization
- Translate operational pain points, edge cases and invoicing requirements into clear product requirements; maintain a living view of integration gaps and their business impact
- Evaluate and define the right long-term integration vision
Commercial & Policy Controls- Design the policy framework that governs enterprise operations and commercial term requirements with customers - including payment release controls, exception handling protocols, and escalation paths
- Partner with GTM and Finance on how VMS growth is modeled, scoped, and operationalized - ensuring new VMS customers are set up for clean execution from day one
Reconciliation & Data Integrity- Own the rebuild of WorkWhile's VMS processes in partnership with the data science team and Finance - covering timesheet matching, worker identity, break/pay rate validation, and exception handling - which are the primary drivers toward accurate invoices sent to customers for collections
- Define and maintain the data quality standards and audit trails required for clean invoicing and payment
Team & Operations- Lead and develop a team executing day-to-day VMS workflows
- Define an automation roadmap, translating manual workflows into product requirements and advocating for Engineering prioritization, allowing the team to shift towards higher leverage activities
- Establish the metrics, dashboards, and operating cadence that give leadership clear visibility into VMS channel health
What We're Looking For- 6+ years of experience in BizOps, strategy & operations, or a technical program management role - ideally at a marketplace, staffing tech, or other usage based model
- Strong analytical foundation - comfortable with SQL or working closely with data teams; able to build and pressure-test models independently
- Experience owning or driving systems integrations in a non-engineering capacity - you don't need to write code, but you need to understand how APIs, data pipelines, and reconciliation systems work well enough to discuss smart architectural tradeoffs
- Demonstrated ability to design operational controls and policy frameworks, not just execute against them
- Commercial instincts - you think about unit economics, pricing, and margin, not just process efficiency
- Clear, structured communicator who can operate across ops, product, engineering, and finance stakeholders
- Experience managing or developing early-career team members
Nice to Have- Background in staffing, workforce management, or Vendor Management Systems platforms (Fieldglass, Beeline, Coupa, VNDLY, etc.)
- Experience with billing operations and commercial controls
- Familiarity with API documentation, webhook architecture, or systems integration scoping
Why This Role- You'll have direct ownership over a growth vector that is becoming strategically central to WorkWhile's enterprise growth
- Real business stakes from day one
- You'll work closely with Carmen Chau (Head of Marketplace Growth & Operations) and have significant cross-functional visibility across Ops, Product, and GTM
- WorkWhile is at an inflection point - this is a role where what you build in the next 12 months will shape how the company scales for years
Compensation & Benefits- Competitive base salary + equity in a high-growth, venture-backed company
- Hybrid work culture with office hubs in SF, NY, Seattle & Toronto. Remote possible for right candidate.
- In-person company off-sites
- Medical, dental & vision coverage
- Unlimited PTO
- 401(k) with employer match
- WFH stipend to support your home office setup
WorkWhile has a diverse, mission-driven, and supportive culture-we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we'd love to chat!
