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 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 drink