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Head of Gigs for Work

San Francisco, CANew York, NYExecutive LeadershipHybrid10+ YOE
Summary

Owns end-to-end P&L, GTM strategy, product direction, and operations for Gigs' enterprise phone plan platform serving global companies. Requires 10+ years in high-growth B2B SaaS with P&L ownership experience and cross-functional team leadership.

About the role

What You Will Do

  • Own the Gigs for Work P&L: drive revenue growth, manage costs, and be accountable for key business metrics including ARR, logo acquisition, net revenue retention, and gross margin.
  • Define and execute the GTM strategy: build the sales motion (direct and embedded/channel), pricing & packaging, ICP definition, and competitive positioning for enterprise buyers (IT, HR, Finance, and Procurement leaders).
  • Lead and scale the team: hire and manage a cross-functional team spanning business development, customer success, operations, and growth marketing for the vertical.
  • Drive product strategy: serve as the voice of the customer to Product and Engineering; prioritize features, integrations (Rippling, Deel, Workday, etc.), and platform capabilities that unlock expansion.
  • Build strategic partnerships: develop and manage relationships with HR tech platforms, device management providers, and channel partners to embed Gigs for Work into existing enterprise workflows.
  • Own the customer journey end-to-end: from first touch through implementation, launch, and ongoing account management; ensure world-class NPS and expansion revenue.
  • Manage carrier and connectivity operations: work with the Connectivity team to negotiate carrier contracts, launch new countries, and ensure operational excellence across 50+ markets.
  • Represent Gigs for Work externally: be the face of the product at industry events, in customer executive meetings, and with press and analysts.

What We Are Looking For

  • 10+ years of experience in high-growth B2B SaaS or infrastructure companies, with at least 3–5 years in a GM, Head of Product Line, Head of GTM, or similar P&L-ownership role.
  • Proven track record of scaling a B2B product or vertical from early traction to significant revenue (ideally $5M–$50M+ ARR range).
  • Deep understanding of enterprise sales cycles, including selling to IT, HR, Finance, and Procurement stakeholders.
  • Experience building and leading cross-functional teams (sales, marketing, ops, CS) in a fast-paced, startup or scale-up environment.
  • Strong product intuition — ability to translate customer needs and market trends into product priorities and work closely with engineering teams.
  • Experience with platform/API businesses, partnerships, or embedded distribution models is highly valued.
  • Exposure to telecom, connectivity, or adjacent infrastructure categories (device management, HRIS, expense management) is a strong plus but not required.
  • Exceptional communication skills — able to operate at both the strategic and tactical level, and influence across all levels from ICs to C-suite.
  • Builder mentality — comfortable with ambiguity, bias to action, and an operator mindset. You've built things from 0 to 1 and from 1 to 10.
Skills
B2B SaaSGTM StrategyP&L ManagementEnterprise SalesCustomer SuccessProduct StrategyHRIS IntegrationsPartnershipsTelecom OperationsAPI Platforms