Regional Sales Director

Skedulo
Skedulo

Sales & Business Development

Chicago, IL, USA

Posted on Jun 19, 2026

Introduction

Here at Skedulo we’re on a mission to support the 2.7 billion people in the world—and the companies that employ them—who do not work at a desk every day. Our global teams are collaborative, ambitious, innovative, and passionate about helping our customers realize their fullest potential by enabling their mobile workforces.

The Skedulo team is a tight-knit group of builders who are passionate about shaping our platform that is relied upon daily by thousands of users across the globe. We are looking for motivated, self-starters who share our values, challenge the status quo, and push the pace of innovation in order to accelerate growth. If you’re drawn to solving hard problems and want to help design software that will make a difference in people’s lives, Skedulo is for you. Visit our website to learn more about what Skedulo does and to learn more about our people and team.

Job Description

The Regional Sales Director is responsible for developing and closing new business within an assigned geographic territory. This role will acquire new customers and expand usage of Skedulo products and services within existing closed-won accounts. The Regional Sales Director is accountable for meeting quarterly and annual quotas, proactive deal management, forecast accuracy, and driving customer and prospect adoption in collaboration with internal teams and the Skedulo partner ecosystem. This role may focus on specific geographic regions or verticals based on relevant experience.

Responsibilities

  • Meet and exceed individual sales quotas.
  • Qualify opportunities using Skedulo’s sales methodology and metrics, including customer fit and success criteria.
  • Develop a territory plan and execute it in collaboration with Sales leadership, Solution Consulting, and assigned Account Development Representatives.
  • Leverage internal resources (Senior Executives, Solution Consulting, Customer Success, Marketing, Legal, etc.) during sales cycles and campaigns.
  • Collaborate effectively with peers and key partners to deliver joint value propositions.
  • Identify needs and build relationships with multiple stakeholders across accounts and lines of business.
  • Pursue new business opportunities and recommend or upsell Skedulo products and services.
  • Provide accurate sales forecasts and track revenue using company sales tools.
  • Maintain high data quality and pipeline hygiene in Salesforce for opportunities and forecasts.
  • Prospect proactively using your network, partners, and the provided technology stack (lead generation will also come from Marketing and Account Development).

Minimum Qualifications

  • 5–8 years’ experience selling enterprise-level software solutions.
  • Experience selling value and ROI to C-level executives and line-of-business leaders.
  • Proven track record of achieving sales quotas for the past five years.
  • Strong oral and written English communication and interpersonal skills.
  • Excellent sales presentation skills.

Desired Skills/ Qualifications

  • 10+ years’ experience selling technology or SaaS solutions.
  • Strong business acumen and ability to articulate strategic value.
  • Experience aligning solutions to a customer’s strategic objectives.
  • Ability to manage multiple concurrent sales cycles.

Additional Requirements

  • Up to 25% travel, as required by the company.
  • Must have a valid work visa for the country where the position is posted at the time of hire.

Benefits

Global Offerings

  • Competitive Salary Package
  • New Hire Stock Options
  • Employee Referral Bonus Program
  • 3 Paid Volunteer Days per year
  • A generous budget to spend on setting up your home office or WFH station
  • 100% employer paid access to Udemy (Learning & Development)
  • Paid Parental Leave for both carers (12 weeks)

United States Specific Offerings

  • Competitive Healthcare Benefits (Dental, Vision, Medical)
  • Voluntary STD and Life Insurance Plans
  • 401k - 4% Company Match
  • 7 paid sick leave days per year
  • 20 paid personal leave days per year
  • 10 paid public holiday days per year