Head of Customer Success at LightWork AI
Jack & Jill/External ATSThis 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.
Job Title: Head of Customer Success
Company Description: LightWork AI - AI-powered operating system for property management
Job Description:
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.
Location: London, UK
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.
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.
The ideal candidate:
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.
Who are Jack & Jill?
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.
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.
Next steps
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.
We never post fake jobs
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.