Regional Sales Manager, Mid-Market

Fleetio

54d•Remote

About The Position

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 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=IlvIbwZT3oU Our careers page: https://www.fleetio.com/careers 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 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=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

Requirements

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

Responsibilities

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”

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