Regional Sales Manager, Mid-Market

We're looking for a Regional Sales Manager, Mid-Market who will be responsible for scaling our sales results in a huge market. You’ll be responsible for leading one of our Mid-Market Sales Teams on its way to capture a total addressable market of tens of thousands of businesses.

A little about us…Fleetio is a modern software platform that helps thousands of organizations around the world 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 Series D in June 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=IlvIbwZT3oU
• 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.