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# Regional Sales Manager, Mid-Market

Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move.

[Apply for this job](#job-application)[View company](https://jobicy.com/company/fleetio.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUndisclosedDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceDirectorPublished14 Oct 2026Apply before13 Nov 2026Listing views20Application actions2Application toolkit

## Make your next move.

Prepare your resume, explore your fit, and draft a cover letter for this opportunity.

AI Summary

## The role, at a glance.

Fleetio is hiring a remote US Regional Sales Manager to lead its Mid-Market B2B SaaS account-executive team. The manager will own team activity, pipeline and funnel management, forecasting, negotiation performance, KPI tracking, and alignment with broader sales objectives. The role has substantial people-leadership responsibilities, including coaching, hiring, performance management, compensation management, and career-path development. Candidates need at least three years of SaaS sales leadership experience, a record of outperforming team revenue goals, and experience scaling outbound ARR.

## Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

### Job Complexity

4/5EasyHard

### Pace & Pressure

5/5RelaxedFast-paced

### Autonomy Level

4/5GuidedFull ownership

### Communication Load

5/5IndependentCollaborative

AI insightThis is a frontline sales leadership role with direct accountability for a $2M+ team quota, forecasting quality, hiring, and sustained revenue performance. It requires both strategic process improvement and high-frequency coaching of a quota-carrying team.

## Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job median (per year)Market rate$155,000US market range (per year)$125k–$200k0$220.00k

AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No employer salary was disclosed. The yearly cadence and USD market estimate are inferred from the US-based, full-time regional sales-management scope in B2B SaaS; estimates reflect likely annual base-pay positioning and do not represent a disclosed total compensation or commission plan.

## Core skills

Skills and capabilities most closely associated with this opportunity.

[B2B SaaS Sales](https://jobicy.com/jobs?search_keywords=B2B%20SaaS%20Sales.md)[Sales Leadership](https://jobicy.com/jobs?search_keywords=Sales%20Leadership.md)[Team Coaching](https://jobicy.com/jobs?search_keywords=Team%20Coaching.md)[Revenue Forecasting](https://jobicy.com/jobs?search_keywords=Revenue%20Forecasting.md)[Pipeline Management](https://jobicy.com/jobs?search_keywords=Pipeline%20Management.md)[Outbound Sales](https://jobicy.com/jobs?search_keywords=Outbound%20Sales.md)[Quota Management](https://jobicy.com/jobs?search_keywords=Quota%20Management.md)[Sales Strategy](https://jobicy.com/jobs?search_keywords=Sales%20Strategy.md)[KPI Tracking](https://jobicy.com/jobs?search_keywords=KPI%20Tracking.md)[Sales Negotiation](https://jobicy.com/jobs?search_keywords=Sales%20Negotiation.md)[Performance Management](https://jobicy.com/jobs?search_keywords=Performance%20Management.md)[Talent Acquisition](https://jobicy.com/jobs?search_keywords=Talent%20Acquisition.md)[Budget Management](https://jobicy.com/jobs?search_keywords=Budget%20Management.md)[Cross-Functional Collaboration](https://jobicy.com/jobs?search_keywords=Cross-Functional%20Collaboration.md)

Sample interview questionsHow have you improved forecast accuracy for a sales team?I establish clear stage definitions, require evidence-based opportunity inspection, review conversion and aging trends weekly, and compare rep forecasts with historical performance. I then coach to the specific gaps and communicate both commit and risk scenarios to leadership.

Describe how you would help a mid-market team scale outbound-sourced ARR.

I would segment the target market, define ideal-customer and account-prioritization criteria, set measurable activity and quality standards, and inspect conversion by source and persona. I would use the findings to refine messaging, coaching, enablement, and capacity allocation.

What is your approach to managing an underperforming account executive?

I begin with transparent performance data and diagnose whether the issue is skill, activity, process adherence, territory, or motivation. I set a documented improvement plan with weekly milestones, provide targeted coaching and resources, and make timely decisions based on sustained evidence.

How do you motivate a team while maintaining high accountability?

I connect individual goals to a clear team mission, recognize quality execution and outcomes, and make expectations visible and consistent. Regular one-on-ones, practical coaching, and fair use of performance data help create trust without lowering standards.

How would you collaborate with marketing, business operations, and sales enablement?

I would share field insights on lead quality, conversion friction, competitive themes, and enablement gaps through a regular operating cadence. Together, we would prioritize initiatives that improve pipeline creation, sales-cycle efficiency, and rep productivity, then measure their impact.

Opportunity details

## About this role.

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](https://rubyonrails.org/foundation)!

More about our team and company:

* Fleetio overview video: [https://www.youtube.com/watch?v=YoXyXTFWbkg](https://www.youtube.com/watch?v=YoXyXTFWbkg)
* Our careers page: [https://www.fleetio.com/careers](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.

Show more

[Apply now >](https://jobicy.com/jobs/155333-regional-sales-manager-mid-market.md)

>  Annual salary information is not provided for this position. Explore salary ranges for similar roles in our [Salary Directory ›](https://jobicy.com/salaries.md)

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