Director of Technical Delivery

Company Overview

Leena AI is a leading agentic AI platform for the enterprise back office, helping organizations transform their employee experience at scale. Our AI Colleagues move beyond simple chatbots to act as autonomous, specialized digital coworkers that resolve HR, IT, finance, and procurement requests end to end, integrating across systems such as Workday, SAP SuccessFactors, ServiceNow, and Salesforce.

Leena has been recognized as a Leader in its category by Gartner for three consecutive years and partners with global enterprises to bring agentic AI to the center of their digital transformation initiatives.

Team Overview: Global Professional Services

The Global Professional Services team, also known as the Implementation and Managed Services group, is responsible for deploying Leena AI's AI Colleagues across our enterprise client base. This team owns the entire delivery process, from post-sale handoff through go-live and into steady-state customer success, and collaborates closely with Product and Engineering to ensure every deployment lands successfully.

The AI FDE team sits within Global Professional Services and is a net-new function being built out to support Leena's expanding enterprise footprint.

Role overview: Director of Technical Delivery

As the Director of Technical Delivery, you will be entrusted with building and leading Leena AI's AI FDE team from the ground up. This pivotal role demands exceptional technical credibility and leadership to bridge strategic execution with hands-on delivery depth, ensuring every AI deployment is repeatable, high quality, and tightly connected to Product and Engineering. You will be accountable for the people, standards, and delivery quality of the AI FDE function as Leena scales its Global Professional Services organization.

We are seeking a proactive, technically fluent leader to stand up this net-new function and drive strategic outcomes at the intersection of B2B SaaS, AI, and enterprise-level delivery.

Key Responsibilities

• AI FDE Team Leadership: Own the hiring, enablement, and day-to-day performance management of the AI FDE team, and build the org design and capacity plan as customer volume scales.
• Delivery Standards & Governance: Establish and enforce standard operating procedures for implementation, success metrics, and escalation paths, and design the delivery frameworks (methodology, tooling, QA) that make AI deployments repeatable rather than bespoke.
• End-to-End Delivery Lifecycle Ownership: Oversee the full AI delivery lifecycle, from post-sale handoff through solution design, go-live, and the transition into steady-state customer success, ensuring the handoff between Sales, Implementation, and Account Management runs cleanly in both directions.
• Cross-Functional Partnership with Product & Engineering: Serve as a key stakeholder in AI program governance, surfacing platform gaps and closing the loop on field feedback to shape the roadmap.
• Performance & OKR Ownership: Own team OKRs tied to go-live timelines, customer satisfaction, and net revenue retention.
• Executive & Cross-Functional Representation: Represent AI delivery in cross-functional planning with Sales, Customer Success, Product, and Engineering leadership.

Requirements

• Education: BS or BA Degree from an accredited University.
• Professional Experience: 10 to 15 years in development, technical delivery, or professional services engineering leadership within growth-stage SaaS or AI-native companies.
• Direct experience building and scaling customer-facing technical teams (FDEs, engineers, analysts).
• Demonstrated experience presenting to and communicating effectively with senior internal and client stakeholders (C-suite, VPs, Directors).
• Technical Fluency: Former hands-on developer, fluent in architecture diagrams and technical tradeoffs, without needing to write production code.
• Recent, hands-on delivery of AI or ML-powered solutions at a growth-stage SaaS or AI-native company.
• Experience designing SDLC-style frameworks, tooling, and standards that drive repeatable, high-quality delivery outcomes.
• Communication & Leadership: Exceptional written and verbal communication skills, with a demonstrated feedback loop into Product and Engineering that has measurably matured a company's offering.
• Ability to lead through influence across Sales, Product, Success, and Engineering without formal authority over those teams.

Preferred Qualifications

• Prior experience with AI/ML products or technologies is a significant advantage.
• Familiarity with modern delivery or project management tools (e.g., Jira, Rocketlane).
• Experience standing up a delivery function from scratch in a growth-stage or funding-constrained environment.