---
title: 'Regional Sales Manager, Mid-Market at Fleetio'
canonical: 'https://feeny.ai/job/regional-sales-manager-mid-market-fleetio-united-states-bxq4exn0k1cy'
type: 'job'
last_seen: '2026-10-15'
---

# Regional Sales Manager, Mid-Market at Fleetio

- **Company:** Fleetio
- **Location:** United States
- **Work type:** remote
- **Posted:** 2026-10-02
- **Last confirmed live:** 2026-10-15
- **Apply:** https://job-boards.greenhouse.io/fleetio/jobs/5254640007

## Job description

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](https://rubyonrails.org/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 compelling career path that evolves over time with promotional opportunities as well as backfill opportunities to keep the team “right-sized”

## Your experience

- 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

## Benefits

- 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

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.

## About Fleetio

## Company Overview
- **One-liner**: Fleetio provides a comprehensive fleet management software platform that helps organizations track, analyze, and improve their vehicle maintenance, compliance, and operational spend.
- **Entity Type**: Private (Series D, 2025)
- **Headquarters**: Birmingham, Alabama, United States
- **Founded**: 2012
- **Founders**: Tony Summerville (Founder & Executive Chairman)

## Core Business
- **Primary industry**: Fleet management software / SaaS for vehicle and equipment operations
- **Target customers**: B2B – any organization with a fleet, including construction, government, trucking & freight, service providers, and small to large enterprises (fleets of 10 to thousands of vehicles)
- **Mission**: "Make it easy to manage a fleet so organizations can spend more time focusing on their own mission."

## Products & Services
- **[Fleetio Platform](https://www.fleetio.com/)**: A cloud-based SaaS platform for managing vehicle maintenance, compliance, fuel, drivers, parts, and equipment. Features include automated maintenance scheduling, AI-powered service assessments (AI Service Advisor), telematics integrations, smart document uploads, cost controls, and real-time reporting. Integrates with a network of 80,000+ repair shops for outsourced maintenance approvals.
- **[Auto Integrate](https://www.linkedin.com/company/fleetio/life)** (acquired 2025): Adds capabilities for automated vehicle inspection and data capture.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metric**: Total Funding of **$620.1M** (as of April 2025) and estimated annual revenue of **$16M** (LinkedIn estimate, 2025)
- **Notable Investors/Partners**: Goldman Sachs Alternatives (lead in Series D), Elephant (lead in Series B, C, and co-lead in Series D), Samsara (ISV Partner of the Year 2024)
- **Growth Signals**: 
  - Headcount grew **28.9% YoY** to 377 employees (2025)
  - Raised **$450M Series D** in April 2025
  - Acquired **Auto Integrate** in March 2025
  - Recognized as **Fast Company Most Innovative Companies** (2025), **IoT Breakthrough Fleet Platform of the Year** (2025), and **Forbes Best Fleet Management Software** (2023-2024)
  - Over **1,000,000 fleet assets** powered by the platform

## Competitive Advantages
- **Comprehensive all-in-one platform**: Combines maintenance, compliance, fuel, driver, and spend management in a single system, reducing complexity for fleet operators.
- **AI-powered intelligence**: AI Service Advisor evaluates repair orders, flags exceptions, and automates approval workflows, turning raw data into actionable insights.
- **Large partner network**: Integration with 80,000+ repair shops and telematics providers (e.g., Samsara) creates a strong ecosystem moat.
- **High customer satisfaction**: 4.8/5 rating based on over 1,000 reviews on G2 and Capterra.
- **Remote-first culture since founding**: Attracts top talent across the US, Canada, and Mexico.

## Strategic Focus
- **Expanding AI capabilities**: Embedding practical intelligence into workflows to help fleet managers make faster, data-driven decisions.
- **Scaling to larger enterprises**: Series D investment and hiring for public sector and enterprise account executives signal a push into government and large commercial fleets.
- **Geographic growth**: Already serving customers in 100+ countries, with plans to deepen presence through acquisitions (Auto Integrate) and new market segments.

## Why Work Here
- **Remote-friendly**: Fully remote positions available across the US, Canada, and Mexico, with a central HQ in Birmingham for optional collaboration.
- **Culture & values**: Emphasizes ownership, intelligence, intensity, and integrity. Recognized as one of Birmingham Business Journal's Best Places to Work for five consecutive years.
- **Perks & benefits**: 401k match up to 4%, comprehensive health & wellness plans, four weeks PTO + 12 company holidays + 2 floating holidays, parental leave for all parents, stock options for all employees, and an annual professional development allowance.
- **Engineering culture**: Built on Ruby on Rails; Fleetio is a founding member of The Rails Foundation. Teams work on AI, integrations, and scalable infrastructure.
- **Growth opportunities**: Fast-growing company (28.9% headcount growth YoY) with a clear path for career advancement and exposure to cutting-edge fleet technology.

## Sources
1. [fleetio.com - About page](https://www.fleetio.com/about)
2. [fleetio.com - Careers page](https://www.fleetio.com/careers)
3. [fleetio.com - Homepage](https://www.fleetio.com/)
4. [Greenhouse - Fleetio jobs](https://job-boards.greenhouse.io/fleetio/jobs/5149262007)
5. [LinkedIn - Fleetio Life](https://www.linkedin.com/company/fleetio/life)

## Other roles at Fleetio

- [Partner Development Manager](https://feeny.ai/job/partner-development-manager-fleetio-united-states-4yy3v0fa81w5) — United States
- [Senior Platform Engineer](https://feeny.ai/job/senior-platform-engineer-fleetio-united-states-2jhkbhht78y9) — United States
- [Senior Lifecycle Marketing Manager](https://feeny.ai/job/senior-lifecycle-marketing-manager-fleetio-united-states-abestt9spzn4) — United States
- [Senior Software Engineer, Marketplace](https://feeny.ai/job/senior-software-engineer-marketplace-fleetio-united-states-canada-mexico-0gt1wx7jq47x) — United States / Canada / Mexico
- [Senior GTM Systems Administrator](https://feeny.ai/job/senior-gtm-systems-administrator-fleetio-remote-fmw1mzpbk1zb)
- [Senior Revenue Operations Analyst](https://feeny.ai/job/senior-revenue-operations-analyst-fleetio-united-states-zzqv9sgeymw4) — United States
- [Manager, Revenue Operations](https://feeny.ai/job/manager-revenue-operations-fleetio-united-states-s9z3pvh28r7y) — United States
- [Senior Applied Data Scientist, Fleet Intelligence](https://feeny.ai/job/senior-applied-data-scientist-fleet-intelligence-fleetio-united-states-canada-y83b5sxhdrna) — United States / Canada / Mexico
- [Senior Field Marketing Manager](https://feeny.ai/job/senior-field-marketing-manager-fleetio-united-states-jw1grqvz44g1) — United States
- [Partner Enablement Manager](https://feeny.ai/job/partner-enablement-manager-fleetio-united-states-7ez3j0845pdm) — United States