Head of Delivery

Company Description

At Apprentice, we’re building a new way for operational teams to get work done through automation.

Founded by Talpiot and ex-8200 leaders with deep experience in AI systems and products, we’re developing a platform that enables finance teams to automate complex, recurring workflows simply by explaining them. Our first product is live, we have paying enterprise customers, and demand is growing quickly.

We are an early-stage B2B AI company building reliable, deterministic automation for complex, process-heavy environments. Delivering real value to our customers requires rigorous execution, tight collaboration between Product, Engineering, Customer Success and a high bar for quality and scalability from day one.

Role Description

As Head of Delivery & Implementation, you will lead our automation engineering team and scale our client-facing delivery function.

Today, our engineers both build automations and support customers. Your role is to strengthen and operationalize this function - ensuring high-quality delivery, efficient support, and a scalable model as we grow.

You will work closely with customers, Product, R&D, and GTM teams to translate real-world workflows into robust automation solutions. This is a hands-on leadership role in an early-stage environment: close to customers, close to the team, and focused on building structure without slowing momentum.

Responsibilities

• Own end-to-end delivery of client automations: discovery, solution design, build, testing, go-live, and iteration.
• Lead automation engineers to ship reliable, maintainable workflows for structured, process-driven environments.
• Establish standards and patterns to ensure automations remain resilient to data, UI, and process changes.
• Implement lightweight delivery processes (planning, backlog management, QA, release practices) that balance speed and quality.
• Join key client conversations to understand workflows, translate them into clear technical requirements, and manage scope, timelines, and expectations.
• Support pre-sales efforts with technical validation, scoping, and high-impact demos or POCs when needed.
• Oversee the customer support operation run by the automation team, ensuring efficient triage, resolution, and clear communication.
• Act as senior escalation point for complex or high-impact customer issues.
• Introduce practical delivery and support metrics (e.g., time-to-value, response/resolution times, incident trends) and use them to drive continuous improvement.
• Turn recurring issues into structured fixes, reusable patterns, or product feedback rather than one-off solutions.
• Coach and develop automation engineers, set clear expectations, and maintain a high bar for reliability, ownership, and delivery standards.

Experience & Skills

• 5+ years leading delivery, implementation, or similar teams in SaaS or other tech-heavy products.
• Strong technical literacy: comfortable engaging with technical concepts, constraints, and discussions while partnering closely with developers (no daily coding required).
• Strong analytical and logical problem-solving skills, particularly in anticipating edge cases and designing solutions that remain stable yet flexible as processes and data evolve.
• Proven experience working with delivery and/or support metrics (e.g., time-to-value, quality, response/resolution times, customer satisfaction) to drive team and process improvements.
• Clear, confident communication skills in English across customers, developers, Product, and R&D, with the ability to set realistic expectations and navigate challenging conversations.
• Fluency in English.