JOBSEARCHER

Head of Customer Success at High-Growth AI Startup (18x Revenue Growth)

Jack JillNew York, NYMay 18th, 2026
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.Job TitleHead of Customer SuccessSalaryNot DisclosedCompany DescriptionHigh-growth AI startup automating payroll and HR operations for PEOsJob DescriptionAs the founding Head of Customer Success, you will build the CS function from the ground up for a startup that 18x’d its revenue last year. You will own the entire post-sales lifecycle, from technical implementations to long-term account growth, while directly influencing the product roadmap for our industry-leading AI agents.LocationNew York or West Palm Beach, USAWhy this role is remarkableJoin as employee #7 at an explosive AI startup that achieved 18x revenue growth in a single year, offering significant founding-team equity.Shape the entire customer success strategy and operational playbook from scratch rather than just following an existing corporate process.Work directly with founders and top industry advisors to define how AI transforms operations for the massive Professional Employer Organization (PEO) market.What You Will DoLead end-to-end customer implementations and onboarding, ensuring clients realize the full value of AI-powered payroll and inquiry automation.Build and codify the company’s customer success processes, including health scoring, renewal playbooks, and proactive account management strategies.Act as the voice of the customer by translating user feedback into actionable insights for the product and engineering teams to drive innovation.The ideal candidateProven track record in B2B SaaS customer success, specifically within early-stage environments where you have built processes from zero to one.High-ownership mindset with the ability to thrive in an intense, ambiguous startup atmosphere where you wear multiple hats simultaneously.Exceptional communication skills and an analytical background, capable of managing complex stakeholder relationships with low ego and high impact.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 stepsStep 1. Visit the job listing.Step 2. Click 'Talk to Jack', or go straight there: https://www.jackandjill.ai/jobs/head-of-customer-success-at-high-growth-ai-startup-18x-revenue-growth-6bf54408-b489-4530-ac64-3f914c3306cc?utm_source=linkedin&utm_medium=job_post&utm_campaign=featured_role_6bf54408-b489-4530-ac64-3f914c3306ccStep 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 jobsThis 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.