Regional Sales Manager

TL;DR

Regional Sales Manager (SaaS): Managing and coaching outbound sales teams to drive growth in an AI-powered labor marketplace with an accent on pipeline optimization and mid-enterprise deal closure. Focus on scaling the sales organization, refining the sales playbook, and developing high-performing account executives.

Location: Onsite in Chicago, IL or San Francisco, CA

Salary: $133,000 base, $223,000 OTE

Company

An AI-powered labor marketplace connecting millions of skilled hourly professionals with hospitality and logistics companies across North America.

What you will do

• Coach representatives through the full outbound sales cycle, including prospecting, qualification, and pipeline building.
• Analyze pipeline and conversion metrics to identify gaps and implement process or enablement changes.
• Provide senior air cover for mid-enterprise deals, managing complex stakeholder cycles and negotiations.
• Onboard and ramp new Account Executives to accelerate their time to productivity.
• Forecast business performance accurately for the executive team.
• Own and evolve the sales playbook to drive adoption and scalability across the organization.

Requirements

• Must be based in or able to work onsite in Chicago or San Francisco.
• 5+ years of experience exceeding quotas in mid-enterprise sales.
• 2+ years of experience building and managing high-performing remote software sales teams.
• Proven track record of hitting and overachieving sales targets.
• Ability to partner cross-functionally with Marketing, Product, and Engineering teams.

Nice to have

• Experience leading outbound or inside sales teams.
• Proven ability to thrive in fast-paced, high-growth environments.
• Background in organizational cultures that prioritize continuous learning and development.

Culture & Benefits

• Comprehensive medical, dental, and vision plans starting from the date of hire.
• Financial security through a 401K plan and HSA contributions.
• Work-life balance supported by flexible paid time off and 8+ paid company holidays.
• Practical perks including phone and commuter stipends.
• Culture rooted in empathy, trust, candor, and a strong bias for action.