Head of Customer Success (AI)

Location: Remote, United States

Company

Infrastructure for enterprises to build and orchestrate autonomous AI workforces across critical business operations, with roots in logistics and a platform built on voice technology, AI models, and orchestration.

What you will do

• Own the Customer Success function and targets for gross retention, net revenue retention, expansion, and customer health.
• Serve as executive sponsor for strategic enterprise accounts and build relationships with operators, VPs, and C-level stakeholders.
• Hire, onboard, coach, and develop Customer Success Managers while defining career paths and performance standards.
• Build the Customer Success operating model, including segmentation, coverage, health scoring, renewal forecasting, escalation processes, and scalable playbooks.
• Partner with Sales, Deployment, Product, and Engineering on renewals, expansion opportunities, implementation handoffs, and customer value.
• Report Customer Success metrics, risks, and strategy to the executive team and board; select and implement team tools and systems.

Requirements

• 10+ years of experience in Customer Success, Account Management, or a similar customer-facing function at a B2B SaaS or technology company, including 3+ years leading and scaling a team.
• Track record of owning retention, net revenue retention, and expansion targets for enterprise customers.
• Experience building a Customer Success function from an early stage, including hiring, process design, and tooling.
• Strong executive presence and ability to communicate with operators and C-level stakeholders.
• Ability to interpret usage and performance metrics, build clear narratives, and drive decisions from data.
• Technical curiosity and comfort discussing integrations, APIs, workflows, and AI concepts with customers and engineers.
• Ownership mindset and ability to work with speed and ambiguity in a fast-growing startup.

Nice to have

• Hands-on logistics, freight, or supply chain experience, ideally managing large, multi-stakeholder accounts.
• Experience with AI, automation, or voice products.
• Familiarity with TMS, WMS, or CRM systems.
• Spanish, Portuguese, or another language.
• Experience at an early-stage or high-growth startup, ideally from Series A to C.

Culture & Benefits

• Ownership and autonomy over projects with encouragement to ship.
• Operating principles emphasize accountability, craftsmanship, kindness, focused urgency, meritocracy, and first-principles thinking.
• Healthcare, dental, and vision coverage.
• Competitive salary and equity in a high-growth startup.
• Backed by a16z, Y Combinator, Base10, Prysm Capital, and Eurazeo.