SaaS, Logistics, Fleet Management, Enterprise Software

Regional Sales Manager, Mid-Market

RemoteRemoteFull TimeManager / HeadPosted 1 month agoVisa sponsorship available

Is this role right for you?

Upload your resume and get a skill-by-skill breakdown — see exactly where you match, where you're close, and what to highlight. Not a mystery percentage.

Get a tailored resume highlighting what this role needs.

Required skills

Mid-Market
Account Executives
forecasting
KPIs
coaching culture
sales leadership
prospecting
funnel management
negotiating
quota

Nice to have

business acumen
budget management
product knowledge

Role summary

Fleetio is seeking a Regional Sales Manager for their Mid-Market team. This role reports to the Director of Mid-Market Sales and is responsible for leading a team of Account Executives. Key responsibilities include providing mentorship, driving performance through coaching and accurate forecasting, defining and tracking KPIs, and managing the day-to-day activities of the team. The ideal candidate has 3+ years of sales leadership experience in a B2B SaaS company, a proven track record of exceeding revenue targets, and strong skills in forecasting, data-driven decision-making, and talent acquisition. This is a remote, full-time position.

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 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.

Ready to apply?

You'll be redirected to Fleetio's application page.