Regional Sales Manager

Ovii's Interpretation of the Role

Instawork is hiring a Regional Sales Manager to lead and scale remote software sales teams, coach reps through the outbound cycle, and drive pipeline performance using data‑driven insights.

Role Snapshot

• Lead remote sales team
• Coach reps across prospecting to closing
• Drive pipeline metrics and performance
• Partner with Marketing, Ops, Product, Engineering
• Own and evolve the sales playbook
• Develop future sales leaders

Must-Have Requirements

• Coaching reps through outbound sales cycle
• Building and managing remote software sales teams
• Quota‑exceeding sales experience (5+ years)
• Data‑driven pipeline monitoring and analysis
• Forecasting and executive reporting
• quota‑exceeding sales
• mid‑enterprise deal selling

Nice-to-Have Signals

• Experience leading outbound/inside sales teams
• Track record thriving in fast‑paced environments
• Background in learning‑focused cultures
• Experience in cultures that prioritize learning and development
• outbound/inside sales team leadership
• fast‑paced environment experience

Work Setup

• Location: Chicago, United States
• Work mode: ONSITE
• Remote scope: COUNTRY_RESTRICTED
• Remote countries: United States
• Employment type: Full-Time

Eligibility Gates

• Work authorization: US work authorization (CA or IL based)
• Visa sponsorship: no

Not Specified in JD

• Travel requirement
• Security clearance

What You'll Likely Work On

• Coach reps through the full outbound sales cycle, from prospecting to pipeline building
• Monitor pipeline and conversion metrics, then design and execute coaching or process changes to close gaps
• Support complex deals as senior air‑cover, navigating multi‑stakeholder negotiations
• Onboard and ramp new Account Executives to accelerate productivity
• Accurately forecast revenue and present insights to the executive team
• Collaborate with Marketing, Operations, Product, and Engineering on sales‑support initiatives
• Own and continuously improve the sales playbook, driving team adoption
• Develop future sales leaders and share best practices across the organization

Good Fit If You Have

• Experience leading outbound or inside sales teams
• Thrives in fast‑paced, high‑growth environments
• Background in cultures that prioritize learning and development