Director of Sales, SMB

Director of Sales, SMB

About Fleetio

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 $144M in Series C in June of 2023 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:

• Watch our culture videos: https://fleet.io/culture
• Fleetio overview video: https://www.youtube.com/watch?v=IlvIbwZT3oU
• Our careers page: https://www.fleetio.com/careers

Who you are

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.

Your impact

• 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

Your experience

• 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

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