We are looking for a Head of Sales with 5+ years of enterprise SaaS experience to join Wayside as a founding sales hire and own end-to-end new logo acquisition in the PEO industry. You'll step into a founder-led sales motion with a proven playbook ($1.2M active pipeline, 40% close rate from discovery) and refine it to aggressively drive revenue growth — working directly alongside the co-founders as the third non-engineering hire.
What will you be doing?
Key Requirements
Wayside helps PEOs and HR teams save time, reduce costs, and drive operational efficiency by using AI to automate end-to-end processes. It integrates into existing channels like Outlook, PrismHR, iSolved, existing
CRMs, and more
Salary
$125,000 - $175,000
Equity
1% - 2%
Location
Remote
Last stage
Seed
Investors
No applications, no recruiter spam. Just the intro.
A few questions to make sure this role is the right shape for you. Two minutes.
I write the intro, send it to the founder, and handle the back-and-forth.
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.