Regional Sales Manager, Mid-Market

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

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