Regional Sales Manager
instawork • Chicago, Illinois, United States; San Francisco, California, United States
Posted: August 5, 2026
Job Description
At Instawork, we're a full staffing platform suite that allows businesses to connect with professionals in a modern, robust way. Our labor marketplace connects over 10M professionals to top Hospitality and Logistics companies across North America, and we're looking for top talent to help us scale. We have an immediate opening for a Sales Manager with a proven track record of success to join our rapidly growing team. Reporting to the Sales Director, this role is a critical member of the sales leadership team, responsible for coaching reps through every stage of the outbound sales process, including prospecting, qualification, and pipeline building, while using data to spot gaps and drive the fixes that close them. This is a results-driven position built for someone who can build and manage remote software sales teams, and who is as comfortable in a rep's deal review as they are in a pipeline dashboard.
What You'll Do & Who You Are
- Coach reps through the full outbound sales cycle (prospecting, qualifying, and building pipeline), with 2+ years of experience building and managing high-performing remote software sales teams
- Read the data and act on it: monitor pipeline, activity, and conversion metrics to spot gaps, then design and execute the coaching, process, or enablement changes that close them
- Bring 5+ years of quota-exceeding experience selling mid-enterprise deals, with a track record of overachievement and hitting sales targets
- 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
- Know the Instawork platform deeply enough to coach reps on value proposition, positioning, and strategy
- Own and evolve the sales playbook, driving adoption across your team
- Develop future sales leaders and share learnings and best practices across the company
- Scale the organization sustainably as the team grows
You're a self-starter who's passionate about coaching, mentorship, and team management, motivated by helping people grow, self-aware, and high in emotional intelligence. You learn fast, establish credibility quickly, and thrive in a high-growth, rapidly changing marketplace. You're excited to build a career at a startup disrupting the gig economy, and you're 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
For CA or IL-Based Applicants
- The base salary for this position is $133,000 base, with an OTE of $223,000 (uncapped sales incentive pay)
- This position is eligible for equity in the form of stock options
- This position is eligible for Instawork benefits, including:
- A 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
#LI-Onsite
Additional Content
At Instawork, we're a full staffing platform suite that allows businesses to connect with professionals in a modern, robust way. Our labor marketplace connects over 10M professionals to top Hospitality and Logistics companies across North America, and we're looking for top talent to help us scale. We have an immediate opening for a Sales Manager with a proven track record of success to join our rapidly growing team. Reporting to the Sales Director, this role is a critical member of the sales leadership team, responsible for coaching reps through every stage of the outbound sales process, including prospecting, qualification, and pipeline building, while using data to spot gaps and drive the fixes that close them. This is a results-driven position built for someone who can build and manage remote software sales teams, and who is as comfortable in a rep's deal review as they are in a pipeline dashboard.
What You'll Do & Who You Are
- Coach reps through the full outbound sales cycle (prospecting, qualifying, and building pipeline), with 2+ years of experience building and managing high-performing remote software sales teams
- Read the data and act on it: monitor pipeline, activity, and conversion metrics to spot gaps, then design and execute the coaching, process, or enablement changes that close them
- Bring 5+ years of quota-exceeding experience selling mid-enterprise deals, with a track record of overachievement and hitting sales targets
- 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
- Know the Instawork platform deeply enough to coach reps on value proposition, positioning, and strategy
- Own and evolve the sales playbook, driving adoption across your team
- Develop future sales leaders and share learnings and best practices across the company
- Scale the organization sustainably as the team grows
You're a self-starter who's passionate about coaching, mentorship, and team management, motivated by helping people grow, self-aware, and high in emotional intelligence. You learn fast, establish credibility quickly, and thrive in a high-growth, rapidly changing marketplace. You're excited to build a career at a startup disrupting the gig economy, and you're 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
For CA or IL-Based Applicants
- The base salary for this position is $133,000 base, with an OTE of $223,000 (uncapped sales incentive pay)
- This position is eligible for equity in the form of stock options
- This position is eligible for Instawork benefits, including:
- A 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
#LI-Onsite