Regional Sales Manager

Instawork • Chicago, IL

7d • Onsite

About The Position

Instawork is seeking a Sales Manager with a proven track record of success to join their rapidly growing team. This role reports to the Sales Director and is a critical member of the sales leadership team. The Sales Manager will be responsible for coaching sales representatives through the entire outbound sales process, including prospecting, qualification, and pipeline building. They will utilize data to identify and address gaps, driving improvements to close them. This is a results-driven position for someone who can build and manage remote software sales teams, comfortable with both direct rep coaching and pipeline analysis. The company's mission is to create meaningful economic opportunities for skilled hourly professionals globally, with their AI-powered labor marketplace supporting local businesses and advancing robotics and AI technology. Instawork's platform connects over 10 million professionals to top Hospitality and Logistics companies across North America.

Requirements

• 2+ years of experience building and managing high-performing remote software sales teams
• 5+ years of quota-exceeding experience selling mid-enterprise deals, with a track record of overachievement and hitting sales targets
• Passionate about coaching, mentorship, and team management
• Motivated by helping people grow
• Self-aware and high in emotional intelligence
• Learn fast, establish credibility quickly, and thrive in a high-growth, rapidly changing marketplace
• Committed to developing a deep understanding of Instawork's mission, values, and product

Nice To Haves

• Experience leading outbound/inside sales teams
• A track record of thriving in fast-paced environments
• A background in cultures that prioritize learning and development

Responsibilities

• Coach reps through the full outbound sales cycle (prospecting, qualifying, and building pipeline)
• Monitor pipeline, activity, and conversion metrics to spot gaps, then design and execute coaching, process, or enablement changes to close them
• Support deals directly as senior air cover, managing multiple stakeholder deal cycles and helping the team navigate complex organizations and negotiations
• Onboard and ramp new Account Executives, accelerating their time to productivity
• Forecast accurately and represent your business clearly to the executive team
• Partner cross-functionally with Marketing, Operations, Product, and Engineering to develop and execute initiatives that support the sales org
• Coach reps on value proposition, positioning, and strategy by deeply understanding the Instawork platform
• Own and evolve the sales playbook, driving adoption across the team
• Develop future sales leaders and share learnings and best practices across the company
• Scale the organization sustainably as the team grows

Benefits

• Variety of medical, dental, and vision plans with coverage beginning on the date of hire
• Flexible paid time off
• At least 8 paid company holidays annually
• Phone stipend
• Commuter stipend
• Supplemental pay on qualified leaves
• Employee health savings account (HSA) contribution
• Flexible spending plans
• 401K plan
• Perkspot: discount program through Lumity
• Equity in the form of stock options

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed