Engineering Manager, Customer Experience

Join the Future of Commerce with Whatnot!

Whatnot is the largest live shopping platform in North America and Europe to buy, sell, and discover the things you love. Whether it's trading cards, fashion, electronics, or live plants, our sellers are building real businesses across hundreds of categories. We're building live commerce at a scale that's never been done in the West, and there's no playbook to copy. The people here are shaping how an entirely new industry develops.

As a remote co-located team, we're inspired by our values and anchored in hubs across the US, UK, Ireland, Poland, Germany, and Australia. We move fast, stay close to our users, and focus on the work that drives the most impact.

We're one of the fastest growing marketplaces and were recently named the #1 Best Startup Employer in America by Forbes. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business and bring people together through commerce.

Role

The Customer Experience Engineering team builds the systems that help buyers and sellers get support when something goes wrongand the products, platforms, and intelligence that make that support scalable.

This is a high-impact engineering leadership role at the intersection of customer experience, marketplace operations, automation, and trust. Seller Provided Support (SPS) is one of our most important initiatives: it enables sellers to resolve buyers' post-purchase issues, strengthens buyerseller trust, and reduces avoidable support volume and refunds. But SPS is one part of a much broader CX portfolio.

You will lead the engineering strategy and execution for the full CX experience, including SPS, CX Inbox, buyer and seller native support flows, and LLM-based chat. You will also guide the platforms and foundations behind these experiences, including the unified support-request lifecycle, rules and workflow systems, structured context, observability, experimentation, and reliable integrations with the systems our agents and operations teams use. A key part of the opportunity is moving CX from fragmented, reactive interactions toward proactive, context-rich support that can understand the underlying issue, route it intelligently, and help resolve it in one coherent journey.

This role is end-to-end. You will own outcomes, technical strategy, organizational health, and execution across multiple workstreams. You will work closely with Product, Design, Operations, Trust, Fraud, Data Science, ML/LLM Platform, Logistics, Payments, and other engineering teams to build a coherent support experience rather than a collection of disconnected flows.

Success looks like a CX organization that scales with Whatnot's growth: buyers and sellers receive clearer and faster resolutions in a coherent experience, support can proactively intervene before frustration compounds, sellers have the tools and configurability to run a scaled business, agents focus on the highest-risk and most complex cases, automation is safe and measurable, and feedback from escalations, CSAT, sentiment, and agent behavior continuously improves our products and policies. The engineering team delivers with speed, quality, and strong operational discipline.

What you'll do:

• Bring deep Customer Experience domain expertise and relevant industry knowledge to shape what Whatnot should invest in and build next. Set the technical vision and multi-year roadmap for Customer Experience Engineering, connecting product and platform investments to customer trust, seller success, support efficiency, refund economics, and company growth.
• Lead a team of approximately 812 engineers across multiple product and platform workstreams; create clarity around ownership, sequencing, staffing, and trade-offs while hiring, coaching, and developing engineers and engineering leaders.
• Own the strategy and end-to-end outcomes for the CX portfolio - including SPS, CX Inbox, buyer and seller native support flows, and LLM-based chat - ensuring these experiences work together as one coherent support journey.
• Guide the development of LLM-powered and automated support experiences, including Sierra, with high standards for quality, evaluation, guardrails, human escalation, auditability, and safe rollout.
• Partner with Product, Design, and Operations to turn ambiguous customer, marketplace, and business problems into simple, coherent experiences that work across users, countries, sellers, carriers, and support teams.
• Build strong, durable partnerships with CX Operations, Trust & Safety, Fraud, Seller Operations, Data Science, ML/LLM Platform, Logistics, Payments, and adjacent engineering teams. Align on shared goals, define clear contracts, and make dependencies visible early.
• Lead the foundations that make CX scalable: unified support-request data and lifecycle events, structured context, rules and workflow orchestration, traceability, experimentation, quality measurement, and reliable integrations with Zendesk and other support systems. Enable configurable seller workflows and dynamic agent tooling that reduce mental load without hiding risk.
• Improve decisioning across classification, context gathering, refunds, logistics, seller responsibility, returns, replacements, and abuse mitigation. Establish configurable and auditable sources of truth for policy and automation, and use signals from escalations, CSAT, sentiment, and interaction outcomes to make support more proactive and self-evaluating.
• Establish a high bar for production readiness, observability, testing, incident response, rollout controls, and holiday-season preparedness. Represent CX Engineering in broader technical and business discussions, clarify the most important problems, and make pragmatic decisions when customer, operational, technical, and financial considerations are in tension.

We offer flexibility to work from home or from one of our global office hubs, and we value in-person time for planning, problem-solving, and connection. Team members in this role must live within commuting distance of our New York City, Seattle or San Francisco hub.

You

People who do well at Whatnot tend to be comfortable figuring things out as they go, biased toward action, and genuinely curious about what they're building. They care more about outcomes than credit and stay close to the product and the people using it.

In addition to embodying our cultural principles, great leadership candidates will also have:

• 8+ years of experience in product or platform engineering, including 5+ years managing engineering teams.
• Experience leading a team or organization through multiple concurrent, technically complex workstreams-not just delivering a single feature or launch.
• A track record of building high-impact, end-to-end customer experiences and the backend systems that support them at scale.
• Strong product judgment: the ability to translate strategic user, operational, and business problems into clear priorities and excellent experiences.
• Technical depth in distributed systems, APIs, data models, event-driven systems, third-party integrations, experimentation, or observability, with the ability to lead architecture discussions and make pragmatic trade-offs.
• Experience partnering deeply with Operations or other business teams whose workflows, tooling, and outcomes are directly affected by engineering decisions.
• The ability to build trusted partnerships across Product, Design, Data Science, ML/LLM, Trust, Fraud, Logistics, Payments, and platform engineering.
• A strong ownership and execution mindset: you surface risks early, create clarity in ambiguity, unblock teams, and stay accountable for outcomes through launch and iteration.
• A people-leadership track record that includes hiring, coaching, developing senior engineers, and building teams that deliver with speed and quality.
• The ability to balance rapid iteration with appropriate safeguards when systems affect customer money, seller livelihoods, trust, fraud exposure, or support operations.

Nice to have

• Experience with customer support, messaging, case-management, workflow, or operations platforms.
• Experience building or operating AI/LLM-powered user experiences, agent-assist systems, or automation with measurable quality and safety guardrails.
• Experience with marketplaces, commerce, logistics, payments, refunds, or trust and fraud systems.
• Familiarity with Python, Elixir, Postgres, mobile clients, or large-scale experimentation platforms.

Benefits

• Flexible Time off Policy and Company-wide Holidays (including a spring and winter break)
• Health Insurance options including Medical, Dental, Vision
• Work From Home Support
  • Home office setup allowance
  • Monthly allowance for cell phone and internet
• Care benefits
  • Monthly allowance for wellness
  • Annual allowance towards Childcare
  • Lifetime benefit for family planning, such as adoption or fertility expenses
• Retirement; 401k offering for Traditional and Roth accounts in the US (employer match up to 4