Director of Sales, SMB (Remote)


Birmingham, AL, USA Remote

Sales Leadership

ERP Software

Feb 24


We're looking for a Director of Sales, SMB to lead our SMB Sales organization into our next phase of growth. This position will have a huge impact on the trajectory of our company by engaging the largest portion of our TAM with ~20,000 prospective customers. The Director of Sales, SMB will lead the strategic direction and management of our SMB Sales engine to fine-tune, optimize, scale and successfully help the company meet its short and long-term sales targets.

Reporting to the VP of Sales, you will be an integral part of the sales leadership team by providing continuous mentorship for our SMB Leaders; refining our sales process, defining and tracking our KPIs and spearheading recruiting. You will work closely with other leaders in sales, marketing, revenue operations, sales operations, marketing operations, go-to-market systems, and sales enablement to drive the strategy for the sales development team.

About Fleetio

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 a $21M Series B in late 2020 and have grown by 60% YoY while remaining cash-flow breakeven. We’re in a great position to continue our exciting growth trajectory as a company.

More about our team and company:

What you'll be doing

  • Build a scalable outbound strategy that promotes effective prospecting and capture of our massive TAM
  • Map strategy: Lead, set strategy, and grow an account-based and territory-based SaaS sales team focused on new customer acquisition across a massive market
  • Partner with our Business Operations team to guide our Sales team and front-line managers to optimize and transform our current systems, processes, and analytics
  • Focus on data: Leverage our Revenue Operations team to build upon our existing metrics to benchmark our team’s success and use data to guide decisions for future growth
  • Develop and scale the team: Work with Fleetio’s People and Business Operations teams to design the org structure and strategy
  • Partner with our recruiting team to aggressively hire top-notch managers and individual contributors and continuously develop new and existing sales team members
  • Plan programs: Partner with our Enablement, Marketing, and Demand Generation teams on planning key initiatives to drive opportunities and movement through the sales funnel
  • Optimize and scale: lead optimization efforts for all aspects of revenue growth

This is a position we consider essential to the company’s success. Be sure to mention coffee in your cover letter so we know you actually read this.

What's in it for you

  • Work as a strategic operationalist who utilizes a data-driven approach to make decisions and set a clear strategy and operating plan for our sales team to hit ambitious revenue goals.
  • Refine processes, systems, and structures - all focused on scaling our SMB Sales strategy.
  • Elevate our team through new perspectives, ideas, and solutions.
  • Work remotely (within the United States), or at our Birmingham, AL HQ. We strive to promote a strong remote working culture and have done so since 2012.


  • 5+ years of experience leading a high-performing SaaS sales team
  • Ownership mindset — you thrive in problem-solving and crafting solutions
  • Extensive experience in scaling an outbound strategy
  • SMB inside sales experience for a complex SaaS solution
  • A demonstrated track record of exceeding revenue targets in a fast-growing organization
  • Built and lead a world-class Sales organization
  • A genuine interest and excitement in striving toward ambitious goals, hiring and rallying a team around those goals, and leveraging data to help you achieve those goals via methodical execution
  • Successful track record of collecting and managing multiple business line forecasts with accuracy and predictability throughout the entire sales funnel
  • Experience in selling vertical software to a range of buyer personas in a large total addressable market
  • Be able to manage relationships with other strategic leaders across the Sales Division and Company
  • In-depth business acumen with a comprehensive understanding of operational efficiency and scalable systems
  • Ability to influence outcomes with team and peer leaders
  • Organization Design to scale the team and performance
  • Negotiation skills - both with external prospects and internal stakeholders
  • Inspirational communication skills to motivate your team to top performance
  • Innovative thinker that can experiment with new ideas and fail fast
  • Proficient in delegation to optimize time management and task management
  • Trusted by team, cross-functionally, peer leaders and senior leadership

Considered a plus

  • Automotive / Fleet management experience
  • Experience in selling to non-technical buyer personas


  • 100% health/dental coverage (50% coverage for family)
  • Vision insurance
  • Incentive stock options
  • 401(k) match of 4%
  • PTO - 4 weeks
  • 10 company holidays + 2 floating holidays
  • Parental and bonding leave
  • Dependent care and medical FSA
  • Short and long term disability
  • Community service funds
  • Professional development funds
  • Health and wellness initiatives
  • Mac laptop + new hire equipment stipend
  • Monthly catered lunches
  • Fully stocked kitchen with tons of drinks & snacks
  • 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 or emailing

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