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=YoXyXTFWbkgOur careers page: https://www.fleetio.com/careersWho 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 impactManage and own the day-to-day comprehensive activity and output of your team - prospecting, funnel management, forecasting, and negotiatingLead a Team of Individual Contributors to accelerate performance by driving key activities each weekAlign sub-department execution and focus with division-wide goals and objectivesContinually review and recommend changes to process and/or strategy to positively impact sub-department performanceMotivate and empower the team to take ownership of their territory and exceed objectives through coaching and mentorshipLead 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 objectivesLead 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 experience3+ years of experience in a sales leadership role within a B2B SaaS companyProven success managing a team quota of $2M+Proven consistent track record of exceeding assigned team revenue objectivesProven track record and strategy of scaling outbound sourced ARRProven track record of coaching and developing team membersIntermediate business acumen with a comprehensive understanding of forecasting and budget managementData-driven decision-making skillsIn-depth sales process expertise and product knowledgeAbility to identify and attract top talentExperience in transparent performance managementNegotiation skills - both with external prospects and internal stakeholdersInspirational communication skills to motivate your team to top performanceDriven front-line manager with the ability to connect with direct reports and inspire performanceTrusted by the team, cross-functionally, peer leaders, and senior leadership
Benefits Multiple health/dental coverage options (100% coverage for employee, 50% for family)Vision insuranceIncentive stock options401(k) match of 4%PTO - 4 weeks (increases at year two!)12 company holidays + 2 floating holidaysParental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)FSA & HSA optionsShort and long term disability (short term 100% paid)Community service fundsProfessional development fundsWellbeing fund - $150 quarterlyBusiness expense stipend - $125 quarterlyMac laptop + new hire equipment stipendFully stocked kitchen with tons of drinks & snacks (BHM only)Remote working friendly since 2012 #LI-Remote
Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.
This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.
If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.