About the role
We are looking for a Head of Customer Success with 5–10 years of experience to join Wayside as a founding team member and build the customer success function from scratch. You'll own customer implementations, relationships, and product feedback loops for an AI platform that helps PEOs automate operations — all at a company that 18x'd revenue last year and is growing fast.
What will you be doing?
- Taking ownership of customer relationships across small and mid-market segments, including onboarding, training, and ongoing check-ins
- Leading complex product implementations — rolling out AI tools to teams of 5 to 50+ users, managing cross-team dynamics and adoption
- Monitoring customer health with data, diagnosing issues, and building remediation plans when customers aren't seeing expected ROI
- Translating qualitative customer feedback into structured, analytical inputs for the product roadmap
- Building the CS playbook from scratch — defining processes, documentation, and success metrics as the first dedicated CS hire
Key Requirements
- Experience in Customer Success at a US-based B2B SaaS company, ideally at an early-stage startup (<25 employees) or as a founding CSM
- Proven track record leading complex technical product implementations with multiple stakeholders and large user groups (not simple API integrations)
- Strong analytical mindset — ability to interpret data, build analyses, and communicate with numbers (backgrounds in consulting, data analysis, or engineering are a plus)
- Exceptional written communication skills — the team operates in a writing-forward culture using Notion
- US-based and available within +/- 3 hours of US Eastern time
