As 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.
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Head of Customer Success at Reflow AI Inc. (DBA Wayside)
Wayside is revolutionizing how Professional Employer Organizations scale, using AI to automate the heavy lifting of HR and payroll. After 18x-ing revenue last year, they are looking for their first Head of Customer Success to join the founding team. This is a rare opportunity to build a CS function from scratch at a high-momentum AI startup. If you have a background in B2B SaaS, a builder’s mentality, and want to own the post-sales strategy for a platform that is already trusted by top industry leaders, this role is for you.
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Location
New York, United States
Compensation
Not Disclosed
Company
Reflow AI Inc. (DBA Wayside)
Role overview
Wayside is an early-stage AI startup that helps professional employer organizations (PEOs) scale their client operations without scaling headcount, using our suite of AI Agents to automate core business processes.
What you will do
- Lead 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.
Who this is a fit for
- Proven 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.
Why this role is remarkable
- Join 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.
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.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
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 your profile’s a match and Reflow AI Inc. (DBA Wayside) wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.