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Head Of Customer Success Implementation Support At High Growth B2b Ai Saas Startup Remote

Head of Customer Success: Implementation & Support at High-Growth B2B AI SaaS St🌐 Remote💼 Full-time💰 $115,000–$115,000🗓 2026-07-24

Core

Founding Head of Customer Success building the CS function from scratch for an early-stage AI startup serving professional employer organizations (PEOs), focusing on implementation, adoption, and long-term customer relationships.

Role type

Founding Head of Customer Success (B2B SaaS)

Builds

Customer success function, implementation processes, and product feedback loops for AI agents

Domain

B2B SaaS, AI Agents, Professional Employer Organizations (PEOs)

Deliverable

production ML models | product features | dashboards & analysis | client delivery

Required skills

Customer Success leadership, project management, training, customer relationship management, product feedback synthesis, written communication, organizational skills

Preferred skills

Experience in early-stage startups (<25 employees), leading technical product implementations, analytical background (consulting/business/data analyst)

Technologies

AI Agents

Responsibilities

Project-manage customer implementations and train users on the product, build and maintain high-quality customer relationships post-implementation, synthesize customer feedback into product roadmaps

Seniority

Founding team member, high ownership, 50+ hours/week

Rewrite
## About the Role 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. Last year, we 18x'd revenue and are now looking to bring on a founding Head of Customer Success as our third non-engineering full-time hire to help us ensure we deliver a world-class product experience for our customers and build out the customer success function from scratch. As full-time employee #7, you can expect to work on a large variety of things. The core areas of need are: - Implementations: Ensuring customers successfully implement and adopt Wayside. This involves project-managing the implementation and training the customer on the product. - Customer Relationships: Building high-quality relationships with our customers that persist beyond implementation, ensuring continued success with Wayside's product and continued satisfaction with our team. This includes customer support. - Product Roadmapping: Turning customer feedback from your interactions into usable inputs for our product prioritization process. ## Location Remote or Hybrid (In-person available in NYC or West Palm Beach) ## Compensation - Base: $115k - $145k depending on experience - Equity: 0.10% - 0.25% - Benefits: - Health (w/ HSA eligible plans), Dental, and Vision Insurance - 401k ## Requirements ### Required - Ambition. We will set high expectations for you in this role and you should expect to work at least 50 hours per week. - Interest in the ambiguity that comes with early-stage startups. We will offer you a lot of ownership and you will have the opportunity to build a lot of things from the ground up. - Written organizational skills. Our organization is a very writing-forward culture. - Low ego and a growth mindset. Willing to accept and address feedback from team members and customers. - Previous experience in Customer Success Manager or Customer Success leadership roles at US-based B2B SaaS technology companies. - Availability in +/- 3 hours of US Eastern time zone. ### Preferred - Previous experience in Customer Success Manager or Customer Success leadership roles at growing startups with < 25 employees. - Experience leading implementations of technical products. - Previous analytical professional experience like consulting, business analyst, data analyst, etc.. ## How to Apply To apply, please submit your information here: https://waysideai.notion.site/wayside-hcs-jd
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