Head of Customer Success at LightWork AI

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.
She will pick the best candidates from Jack's network

The next step is to speak to Jack.

Head of Customer Success

LightWork AI - AI-powered operating system for property management

You will build the Customer Success function from the ground up for a high-growth startup. Managing an existing team member, you'll own the full post-sale journey-onboarding, adoption, and retention for non-technical property companies. This role combines commercial rigor with technical depth to ensure an autonomous AI agent delivers real-world value.

London, UK

• Founding-level leadership opportunity to define the CS playbook and infrastructure for a category-defining AI agent from day one.
• High-traction environment closing major enterprise deals with a product that autonomously manages maintenance, communications, and compliance.
• True player-coach impact where you scale a team while solving complex change management challenges in a traditional industry.

• Own the end-to-end commercial lifecycle including renewals, health scoring, and identifying expansion ARR opportunities across the portfolio.
• Lead the technical onboarding and adoption process to reduce bypass behavior and ensure Felicity is integrated into client workflows.
• Serve as the voice of the customer, escalating product insights to the engineering team to improve AI reliability and performance.

• 5+ years in Customer Success with 2+ years in leadership, specifically building or transforming functions in a B2B SaaS environment.
• Strong technical fluency or a background in solutions engineering/development to manage API integrations and technical stakeholders.
• Proven track record in change management, successfully driving technology adoption among resistant, non-technical users in traditional industries.

Step 1. Visit our website.
Step 2. Click 'Talk to Jack'.
Step 3. Talk to Jack so he can understand your experience and ambitions.
Step 4. Jack will make sure Jill (the AI agent working for the company) considers you for this role.
Step 5. If Jill thinks you're a great fit and her client wants to meet you, they will make the introduction.
Step 6. If not, Jack will find you excellent alternatives. All for free.

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.
Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.
We appreciate this can make them look a bit suspect, but there isn't much we can do about it.
Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.