Strategic Overview
Regional Sales Manager, Mid-Market at Fleetio is a sales-support opportunity centered on the specialist responsibilities and outcomes described in the employer's listing.
The published role emphasizes work such as 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.
The role is listed for United States with remote working arrangement, giving candidates the practical context needed to assess fit before applying. Relevant signals in the listing include Sales, Director.
Key information at a glance
About This Role
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…
More about our team and company:
Key Responsibilities & Objectives
- 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
Required Qualifications & Candidate Blueprint
- 3+ years of experience in a sales leadership role within a B2B SaaS company
- Proven consistent track record of exceeding assigned team revenue objectives
- Proven track record and strategy of scaling outbound sourced ARR
Salary & Benefits
The available source data does not publish a numerical salary range for this opening. We do not estimate or substitute third-party figures.
- 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
Full Job Description
The following is the complete job description supplied by the source. We sanitize unsafe markup and remove external links, but do not shorten or rewrite the employer's source content.
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:
- Our careers page:
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.
Editor’s Market Perspective (Our Custom Analysis)
Why This Position Matters
This sales-support opening is a useful opportunity for candidates whose experience matches Sales, Director. Its strongest career signal is the scope of the work itself — particularly Manage and own the day-to-day comprehensive activity and output of your team - prospecting, funnel management, forecasting, and negotiating — rather than a generic title alone.
Resume & Application Strategy
For the application, mirror the employer's language where it truthfully matches your background: foreground Sales, Director, quantify outcomes from comparable work, and place the most relevant experience near the top of the resume. If the listing specifies tools, platforms, leadership scope, or domain experience, use those exact terms in context instead of presenting an unrelated keyword list.
We organize source-provided information into this independent job-seeker overview. Compensation is shown only when the source provides it; the official listing remains the authority for current requirements and application instructions.