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Salary: USD 133,000 - 223,000 / annual
Instawork is a labor marketplace platform connecting over 10M skilled hourly professionals with top hospitality and logistics companies across North America. The company is backed by leading investors including Benchmark, Spark Capital, Craft Ventures, Greylock, and Y Combinator.
As Regional Sales Manager, you will report to the Sales Director and serve as a critical member of the sales leadership team. You will build and manage a remote software sales team, coaching Account Executives through the full outbound sales cycle—from prospecting and qualification to pipeline building and deal closure.
Key responsibilities include:
- Coach and develop remote sales reps through prospecting, qualification, and pipeline-building activities
- Monitor pipeline, activity, and conversion metrics to identify gaps and execute coaching, process, and enablement improvements
- Provide senior-level deal support and air cover, managing complex multi-stakeholder negotiations
- Onboard and ramp new Account Executives to accelerate productivity
- Forecast accurately and communicate business performance to the executive team
- Partner cross-functionally with Marketing, Operations, Product, and Engineering on sales enablement initiatives
- Own and evolve the sales playbook, driving adoption across your team
- Develop future sales leaders and share best practices across the organization
- Scale the sales organization sustainably as the team grows
You bring 5+ years of quota-exceeding experience selling mid-enterprise deals, with a proven track record of overachievement. You have 2+ years of experience building and managing high-performing remote software sales teams. You are a self-starter passionate about coaching, mentorship, and team development. You learn quickly, establish credibility rapidly, and thrive in high-growth, fast-paced environments. You are committed to understanding Instawork's mission, values, and product deeply.
