Head of Customer Success: Implementation & Support at High-Growth B2B AI SaaS Startup (Remote)

Company 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. Role 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 Apply tot his job

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