3h ago
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Regional Sales Manager, Mid-Market

United StatesUnited StatesRemotemid
SalesRegional Sales Manager
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Quick Summary

Overview

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,

Technical Tools
SalesRegional Sales Manager

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!

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.

  • 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 compelling career path that evolves over time with promotional opportunities as well as backfill opportunities to keep the team “right-sized”
  • 3+ years of experience in a sales leadership role within a B2B SaaS company
  • Proven success managing a team quota of $2M+
  • Proven consistent track record of exceeding assigned team revenue objectives
  • Proven track record and strategy of scaling outbound sourced ARR
  • Proven track record of coaching and developing team members
  • Intermediate business acumen with a comprehensive understanding of forecasting and budget management
  • Data-driven decision-making skills
  • In-depth sales process expertise and product knowledge
  • Ability to identify and attract top talent
  • Experience in transparent performance management
  • Negotiation skills - both with external prospects and internal stakeholders
  • Inspirational communication skills to motivate your team to top performance
  • Driven front-line manager with the ability to connect with direct reports and inspire performance
  • Trusted by the team, cross-functionally, peer leaders, and senior leadership

 

What We Offer

~1 min read
✓Multiple health/dental coverage options (100% coverage for employee, 50% for family)
✓Vision insurance
✓Incentive stock options
✓401(k) match of 4%
✓PTO - 4 weeks (increases at year two!)
✓12 company holidays + 2 floating holidays
✓Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)
✓FSA & HSA options
✓Short and long term disability (short term 100% paid)
✓Community service funds
✓Professional development funds
✓Wellbeing fund - $150 quarterly
✓Business expense stipend - $125 quarterly
✓Mac laptop + new hire equipment stipend
✓Fully stocked kitchen with tons of drinks & snacks (BHM only)
✓Remote working friendly since 2012 #LI-Remote

Location & Eligibility

Where is the job
United States
Remote within one country
Who can apply
Open to applicants worldwide

Listing Details

Posted
October 2, 2026
First seen
October 2, 2026
Last seen
October 2, 2026

Posting Health

Days active
0
Repost count
0
Trust Level
68%
Scored at
October 2, 2026

Signal breakdown

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Regional Sales Manager, Mid-Market