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.
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London, UKNot Disclosed + Equity
Featured roleLondon, UKNot Disclosed + Equity
Head of Customer Success at LightWork AI — AI property management platform
LightWork AI is looking for a Head of Customer Success to build their CS function from scratch and lead the real-world deployment of Felicity, their autonomous AI agent for property management. This isn't just about renewals; it's a high-impact leadership role requiring a blend of technical depth and commercial sharpness to drive adoption in an industry ripe for disruption. If you're a builder who thrives on change management and wants to define how AI delivers value to enterprise clients, this founding-level opportunity in London is for you.
Overview
Why this role stands out
Company
AI25
LightWork AI - AI-powered operating system for property management
Responsibilities
What you will do
- 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.
Candidate profile
Who this is a fit for
- 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.
What makes it remarkable
Why this role is remarkable
- 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.
Jack & Jill
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
About Jack & Jill
Meet Jack
Jack gets to know what you are great at, what you want next, and makes sure Jill considers you for the right opportunities.
How does this work?
Jack's an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack's network.
If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
Jack