Regional Vice President, Enterprise Sales

Regional Vice President, Enterprise Sales

We’re seeking an exceptional Regional Vice President of Enterprise Sales to spearhead the growth and success of our largest and most strategic markets. As a key member of our sales leadership team, you will design and execute strategies that drive revenue through high-impact enterprise customers—those that have a measurable influence on our overall performance. Your leadership will directly shape the future of our sales team and the company’s trajectory.

In this role, you’ll partner with a talented team of Enterprise Sales Leaders, helping refine sales processes, define and track KPIs, and champion our sales talent strategy. You will collaborate closely with cross-functional leaders in sales, marketing, business operations, and sales enablement to ensure seamless execution and drive revenue-generating initiatives.

About Fleetio

Fleetio is a cutting-edge software platform empowering organizations globally to optimize their fleet operations. As a leader in transportation technology, we’re rapidly expanding and evolving, supported by a successful Series C funding round in June 2023, where we raised $144M. Our culture is innovative, customer-centric, and driven by a passion for excellence. As a proud founding member of the Rails Foundation, we are committed to being at the forefront of modern software development.

Learn more about us:

• Watch our culture videos: Fleetio Culture
• Fleetio overview video: Fleetio Overview
• Our careers page: Fleetio Careers

Your Impact

• Drive Revenue Growth: Lead and empower a team of Sales Managers and Account Executives to expand our market share and hit ambitious revenue targets.
• Initiate High-Impact Strategies: Identify opportunities for business growth and operational improvement while leading initiatives that enhance performance across the team.
• Optimize Sales Processes: Continuously refine sales processes, metrics, and tools to maximize success and ensure alignment with Fleetio’s broader business objectives.
• Forecasting & Coaching: Deliver accurate forecasts, ensure accountability, and provide consistent coaching to drive measurable improvements.
• Collaborate for Success: Partner with Fleetio’s Marketing, Sales Development, Recruiting, and Sales Enablement teams to build a robust pipeline, streamline operational performance, and attract top talent.
• Mentor & Empower: Guide and mentor your team to take full ownership of their territories, empowering them to exceed sales goals and grow within the organization.
• Customer Engagement & Market Insight: Travel to customer meetings and industry events, providing direct feedback from key customers to inform product and marketing strategies.
• Growth Leadership: Lead the charge in scaling a repeatable and efficient sales process designed to secure Fleetio’s largest customers and accelerate overall company growth.
• Be Part of Our A-Player Team: Join an outstanding team that goes above and beyond to make Fleetio a successful, customer-focused organization.

Your Experience

• Leadership Excellence: 5-7 years of experience managing and scaling high-performing sales teams, especially in SaaS environments.
• Proven Success: A history of exceeding revenue targets and managing forecasts with accuracy and predictability across complex sales funnels.
• Sales Expertise: Deep understanding of the full sales cycle—from discovery and demos to objection handling, negotiation, and pipeline management.
• Data-Driven Decision Maker: Skilled at using data to inform decisions, track team performance, and adjust strategies to meet business objectives.
• Strategic Mindset: You’re a problem solver who thrives on creating scalable solutions and building high-impact sales strategies.
• Inspirational Leadership: You excel at motivating teams, cultivating strong relationships with stakeholders, and ensuring team success through both coaching and collaboration.
• Innovation & Adaptability: You bring fresh ideas to the table, continuously looking for ways to improve performance, experiment with new approaches, and iterate quickly.
• Operational Expertise: In-depth knowledge of business operations, systems, and best practices to ensure efficiency at scale.
• Exceptional Communication Skills: Whether negotiating with prospects or presenting to senior leadership, your communication is clear, concise, and impactful.

Benefits

• Multiple health/dental coverage options
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO - 4 weeks
• 12 company holidays + 2 floating holidays
• Parental leave- birthing parent (12 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
• 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.