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
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”
- 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
- 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.
Skills Required
- 3+ years of sales leadership experience within a B2B SaaS company
- Experience managing a team quota of $2 million or more
- Consistent record of exceeding assigned team revenue objectives
- Experience scaling outbound-sourced annual recurring revenue
- Track record of coaching and developing team members
- Business acumen, including 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 with transparent performance management
- Negotiation skills with external prospects and internal stakeholders
- Inspirational communication skills
- Front-line people management and team motivation skills
- Ability to build trust with team members, cross-functional peers, and senior leadership
Fleetio Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Fleetio and has not been reviewed or approved by Fleetio.
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Healthcare Strength — Health coverage includes multiple medical and dental options with full employee-premium coverage, plus vision, HSA/FSA, and employer-paid short-term disability. Core health benefits are consistently presented as comprehensive across official listings.
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Leave & Time Off Breadth — Time off includes PTO that increases with tenure, company holidays, and floating holidays. Paid parental leave is offered for both birthing and non-birthing parents.
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Wellbeing & Lifestyle Benefits — Extras include quarterly wellbeing and business-expense stipends, professional development funds, community service support, and remote-work setup assistance. These perks augment the core package and are emphasized across employer materials.
Fleetio Insights
What We Do
Our software helps organizations around the world track, analyze and improve their fleet operations. We're passionate about making it easy to manage a fleet so our customers can spend more time focusing on their mission.
