Head of Ai Delivery

Responsibilities:

• The post-sale P& L of outcomes: company-level accountability for time-to-live, gross and net revenue retention, adoption, and customer health, with targets you set with the CEO and hit.
• The delivery function itself: design the onboarding playbook, QA standards, health-scoring model, escalation paths, and success metrics that the team is built on, then hire, manage, and develop that team as we scale.
• Hands-on implementation (initially): run structured onboardings from signature to go-live, configure Dextr's AI agents' call flows, knowledge bases, SOPs, integrations and edit and refine prompts to match each property's voice and operating procedures.
• QA and deployment quality: establish and enforce QA hygiene; review agent conversations, score accuracy, catch regressions and build the tooling and rubrics that let the team do it at scale.
• Retention and expansion motion: monitor usage and health data to spot adoption gaps and churn risk early, run proactive plays to deepen engagement, and own renewal and expansion conversations with economic buyers.
• Executive customer relationships: build trusted relationships with GMs, owners, and operations leaders across hotel groups and hospitality brands; you are warm, credible, and the person customers ask for by name.
• The customer voice in the company: feed structured customer insight to product and engineering, shape the roadmap with field evidence, and partner with sales on handoffs, pilots, and reference customers.

Requirements:

• 2-8 years of total experience, including 1-4+ years in implementation, professional services, or technical customer success at a B2B SaaS company with experience leading and hiring for post-sale teams.
• A track record of owning executive-level post-sale metrics (time-to-live, NRR/GRR, adoption) and a clear point of view on how to build the playbooks, staffing models, and tooling that move them.
• Genuinely hands-on technical comfort: you can edit prompts, work with low-code configuration, read a JSON payload, and QA an AI conversation yourself, and you expect to keep doing so, not just manage it.
• Player-coach DNA: you have built a function from an early stage (first post-sale hire, founding CSM/implementation lead, or 01 services team) and know the difference between running the machine and designing it.
• Exceptional interpersonal warmth and executive presence; hospitality customers judge on personality, and yours wins over owners and GMs alike.
• Organised and self-directed: you can run multiple concurrent onboardings and later, a team running dozens without dropping details.
• Willingness to work in-person from our Bengaluru office and travel to Sunnyvale, CA and customer properties.
• Leadership experience at a CCaaS, conversational AI, or voice AI company (contact centre platforms or AI agent products).
• Background in hospitality technology (PMS, guest messaging, restaurant tech) or hands-on hospitality operations experience earlier in your career.
• Experience building QA/evaluation programs for AI or agent conversations.
• Experience presenting retention and delivery metrics to boards or executive teams.