Careers At Routeware

Routeware is a 19-year old software and software-as-a-service (SaaS) company that is part of the rapidly-growing “Internet of Things” (IoT) market in the area of fleet service automation. Based in the Portland, Oregon metro area, we have a successful record of selling fleet automation management software to municipalities and companies of all sizes. In this role, you can make a significant impact within a dynamic, team-centric culture that appreciates innovation, initiative, and creative problem solving. Routeware provides a casual yet professional work environment designed to bring the best out of each member of our team.

REGIONAL Sales Manager:

Various Territories Available

Position Summary

As a key member of our solutions-selling Sales organization, managing remotely you will play an invaluable role in Routeware’s growth strategy and ability to achieve company goals. Our Regional Sales Managers will be an individual contributor focusing largely on new business while also serving existing accounts (hunter/farmer). In this role you will be selling to qualified prospects in a multi-state region while managing qualified leads generated by an ISR team. You will also leverage your own prospecting skills to bolster your pipeline with additional leads, all the while contributing to best practices to support the success of your greater team.


  • Be an impactful player on a high-­performing sales team
  • Be a Routeware ambassador within territory accounts, maximizing our brand recognition and mind-share at all levels, evangelizing our solutions and publicizing success stories
  • Continuously develop deep insights into the Fleet Logistics/Waste Hauling software and services market; to serve customers and drive competitive wins
  • Drive an effective, consultative sales process to hit (and exceed!) your monthly and quarterly quota goals
  • Actively prospect to supplement the lead flow provided by a dedicated team of ISRs
  • Be focused on delivering high customer satisfaction throughout the entire sales cycle of 6 months – 18 months
  • Work collaboratively across departments to execute sales strategy as the firm introduces enhancements to existing solutions and releases new products


  • Confident: You are a natural at conveying value, and you know how to stand your ground
  • Passionate : You love to sell, and you have the track record that shows you are good at it
  • Persuasive : Display the ability to be an expert at navigating difficult conversations and getting buy-in from your customers
  • Adaptable : Live out optimism in the face of adversity and exhibit the passion of an ever-changing environment
  • Solutions-oriented: You have a bias for action and don't give up easily
  • Communications: You write well and make excellent presentations


  • 6-10 years of demonstrably successful outside sales experience with big-ticket, products or services ($200,000 or more per sale) that include computer software or software-as-a-service (SaaS) or network services or other professional services that involve consultative solutions-selling.
  • A demonstrable track record of hitting and exceeding quota, ideally with exposure to President’s club wins or consistent performance in the top 10% of your current or previous company’s sales consultants.
  • Familiarity with strategic selling, formal training or understanding of best practice models such as Miller Heiman, Solution Selling, SPIN or Challenger.
  • Authoritative business and financial acumen to translate customer requirements into meaningful business recommendations.
  • HUNTER mentality with the proven ability to exceed quota for defined geographic territory while maintaining a healthy pipe.
  • The ability to quickly and accurately assess opportunities and realistically forecast likelihood to close based on customer relationship, predictable buying process, budget availability or challenges.
  • Identify and assess opportunities to grow existing accounts or develop new opportunities.
  • Experience selling 6-figure deals.
  • Proficiency with, intermediate (at least) Microsoft Office skills, and home office tools.
  • A high standard of excellence.
  • Great communication and collaboration skills. 

If you are interested in this exciting opportunity, please submit your cover letter and resume to

The preceding position description is intended only to describe the general nature and level of work to be performed by an incumbent employee.  It is not intended to be construed either as an employment contract or as an exhaustive list of all responsibilities, duties, and skills required of persons so classified or assigned.