Regional Sales Manager, Mid-Market
Quick Summary
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,
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!
- 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.
- 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
What We Offer
~1 min readLocation & Eligibility
Listing Details
- Posted
- October 2, 2026
- First seen
- October 2, 2026
- Last seen
- October 2, 2026
Posting Health
- Days active
- 0
- Repost count
- 0
- Trust Level
- 68%
- Scored at
- October 2, 2026
Signal breakdown
Browse Similar Jobs
Stay ahead of the market
Get the latest job openings, salary trends, and hiring insights delivered to your inbox every week.
No spam. Unsubscribe at any time.