PitchMeAI Jobs
Instawork

Regional Sales Manager

Instawork · Chicago, Illinois, United States; San Francisco, California, United States

Posted about 3 months ago

or apply directly on Instawork's site. We never take the application ourselves.

Is this posting real?

This role has been open
79 days
Instawork's roles stay open a median of 82 days
Reposted
No
Salary listed
No
27% of Instawork's roles list one
Ghost-job risk at Instawork
high
59 stale, 0 reposted of 59 open
Hiring momentum
68 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-10-24

Measured from postings appearing on and disappearing from Instawork's own greenhouse board since 2026-08-03. Full hiring picture for Instawork.

About this role

As a Regional Sales Manager at Instawork, you will lead and coach a team of sales representatives through the outbound sales process, focusing on prospecting, qualification, and pipeline building. You will utilize data to identify gaps in performance and implement strategies to address them, while also managing complex deal cycles and collaborating with cross-functional teams to support sales initiatives.

Our read on this posting2.8out of 5
benefits
5/5
freshness
1/5
career value
4/5
role clarity
4/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Instawork as an employer.

What you need

  • 2+ years of experience building and managing high-performing remote software sales teams
  • 5+ years of quota-exceeding experience selling mid-enterprise deals
  • Proven track record of overachievement and hitting sales targets
  • Ability to coach reps on value proposition, positioning, and strategy
  • Experience in onboarding and ramping new Account Executives
  • Strong forecasting skills and ability to represent business to executive team

Nice to have

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

What you get

  • Base salary of $133,000 with an OTE of $223,000
  • Equity in the form of stock options
  • 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

Worth weighing

  • No specific details on the sales tools or technology stack used
  • The role requires managing remote teams, which may involve challenges in communication and collaboration
  • The company emphasizes a high-growth environment, which may lead to rapid changes in expectations and responsibilities

Summarised from Instawork's posting. Read the full original.

Listed by Instawork on their greenhouse job board, last confirmed open on 2026-10-24. PitchMeAI is not the employer.

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