Regional Sales Manager, SMB

Fleetio

115d

About The Position

We're looking for a Regional Sales Manager, SMB who will be responsible for scaling our sales results in a huge market. You’ll be responsible for leading one of our smb 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 June of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

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

What This Job Offers

• Job Type: Full-time
• Career Level: Manager