Overview

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.

In the last year, we 18x’d revenue and are now looking to bring on a founding Head of Sales as our third non-engineering full-time hire to help us more aggressively drive growth and free up founder bandwidth for product management.

In this role you will be joining the founding team alongside co-founders Phil Dakin and Ish Baid.

Our growth is primarily driven through high-value (> $40k ACV) deals sold through our customer’s executive leadership teams.

What makes this role exciting:

• 40% close rate from discovery (55% from proposal)
• $1.2M in active pipeline
• #1 player in the industry with a significant first mover advantage

Role

In this role you will do the following:

• Sales Execution: Run and refine our proven PEO sales playbook to increase the company’s revenue. You’ll work with the founders to start but ultimately own the end-to-end process.
• Influence the Product: You’ll bring back data from your deals as a key input to defining our product’s roadmap.
• Sales Leadership: As we scale our revenue you will be responsible for building out the sales organization.

Location

Remote or Hybrid (In-person available in NYC or West Palm Beach)

Compensation