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
About this job
- Who can apply
- United States
- Posted
- 20 days ago
Listing Details
- Posted
- October 2, 2026
- First seen
- October 2, 2026
- Last seen
- October 23, 2026
Posting Health
- Days active
- 20
- Repost count
- 0
- Trust Level
- 37%
- Scored at
- October 23, 2026
Signal breakdown
Fleet maintenance software for fleets of all sizes. Control the chaos of fleet maintenance and management with Fleetio!
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