Regional Sales Manager, Mid-Market

A little

about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company.

Fleetio is also a proud founding member of the Rails Foundation!

More about our team and company:

Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg Our careers page: https://www.fleetio.com/careers

Who you are

Reporting to the Director of Mid-Market Sales, you will be an integral part of the sales leadership team. You will provide continuous mentorship for our Mid-Market Account Executives, deliver stellar results backed by accurate forecasting, define and track our KPIs, and spearhead a coaching culture that breeds continuous improvement.

You will work closely with other leaders in sales, marketing, business operations, and sales enablement to drive the strategy for this team.

Your impact

Manage and own the day-to-day comprehensive activity and output of your team - prospecting, funnel management, forecasting, and negotiating Lead a Team of Individual Contributors to accelerate performance by driving key activities each week Align sub-department execution and focus with division-wide goals and objectives Continually review and recommend changes to process and/or strategy to positively impact sub-department performance Motivate and empower the team to take ownership of their territory and exceed objectives through coaching and mentorship Lead sub-department meetings and actively participate in divisional meetings, Sales Kick-offs, etc.

Collaborate with divisional peers with the intent to collaborate on achieving top objectives Lead people management efforts for the sub-department - hiring, off-boarding, performance management, compensation, etc. Cultivate and manage a com