About the role
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?
- Own the full sales cycle end-to-end — from prospecting to close — for high-value deals ($46K mean ACV, targeting six-figure deals upmarket)
- Shadow founder-led deals in your first 30 days, then progressively take ownership of small/mid-market and upmarket deals by day 90
- Refine and build out the sales playbook, bringing structure and repeatability to a motion that's already generating strong results
- Sell into PEO executive leadership (CEOs, COOs, VPs of Operations) and navigate multi-stakeholder deal cycles
- Bring market signals and customer insights back to the product team to influence the roadmap
Key Requirements
- Proven experience as an early-stage / founding salesperson is a must have — must thrive in ambiguity and build 0-to-1 without an established playbook
- Consistent quota over-attainment in enterprise SaaS sales, ideally closing deals in the $50K–$100K+ range
- Strong prospecting and outbound skills — this is a self-sourced pipeline role, not an inbound-heavy motion
- PEO or adjacent industry knowledge (HR tech, payroll, ASOs) is a major plus and highly weighted
- Low ego, excellent written communication, and a process-oriented mindset aligned with a writing-forward culture
