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Headway

Director of Product, CX Product

Leads product vision and team for customer experience platform, building AI-powered self-service, proactive engagement, unified channels, and agent tools to cut costs and boost satisfaction. Requires 8+ years product leadership with CX/AI experience managing PMs.

250k – 312kNew York, NYSan Francisco, CASeattle, WAProduct ManagementHybrid8+ YOE
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About the role

Responsibilities

  • Define the vision and strategy for Headway's CX product — spanning AI-powered resolution, agent tooling, proactive engagement, channel strategy, knowledge systems, and feedback loops that connect support insights back to the product.
  • Build and lead a team of product managers focused on reducing cost-to-serve while increasing resolution quality and customer satisfaction.
  • Own the AI resolution layer — build agentic workflows and API integrations that enable AI to resolve problems; define autonomy framework.
  • Build proactive engagement systems that contact customers before problems arise.
  • Launch and unify contact channels (email, text, voice) with intelligent routing based on customer context.
  • Own knowledge and quality layer — machine-readable SOPs, AI evaluation frameworks, crisis escalation.
  • Partner with CX Operations to build agent tooling (AI copilot, journey context, auto-summaries).
  • Close feedback loops to identify product defects driving support volume.
  • Establish measurement frameworks connecting CX investments to business outcomes.

Requirements

  • 8+ years product leadership experience, including 3+ years managing PMs.
  • Track record building CX/support products at scale.
  • Strong POV on AI transforming customer support; shipped AI-powered CX products.
  • Launched/scaled multi-channel CX systems with intelligent routing.
  • Demonstrated ability to reduce support costs while improving satisfaction.
  • Thrive at product/operations intersection.

Nice to Haves

  • Experience in healthcare, insurance, or complex customer interactions.

Compensation

  • Base pay: $249,600 - $312,000 (depending on qualifications, experience, location).
  • Equity compensation.
  • Comprehensive benefits: medical/dental/vision, HSA/FSA, 401K, WFH stipend, therapy reimbursement, parental leave, fertility benefits, holidays, flexible PTO, EAP, training.

Skills

AIProduct ManagementCustomer ExperienceCxIntelligent RoutingMulti-Channel SupportAgent ToolingAPI IntegrationsWorkflow AutomationFeedback LoopsMetrics Frameworks

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