Regional Vice President, Enterprise Sales

Summary

Join Fleetio as our Regional Vice President, Enterprise Sales and lead the growth of our largest markets. You will design and execute strategies to drive revenue, partnering with a team of sales leaders. Responsibilities include refining sales processes, defining KPIs, and championing our sales talent strategy. You will collaborate with cross-functional leaders to ensure seamless execution and drive revenue-generating initiatives. This role requires significant experience managing high-performing sales teams in SaaS environments and a proven track record of exceeding revenue targets. You will mentor and empower your team, fostering a culture of success and collaboration.

Requirements

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

Responsibilities

• Lead and empower a team of Sales Managers and Account Executives to expand our market share and hit ambitious revenue targets
• Identify opportunities for business growth and operational improvement while leading initiatives that enhance performance across the team
• Continuously refine sales processes, metrics, and tools to maximize success and ensure alignment with Fleetio’s broader business objectives
• Deliver accurate forecasts, ensure accountability, and provide consistent coaching to drive measurable improvements
• Partner with Fleetio’s Marketing, Sales Development, Recruiting, and Sales Enablement teams to build a robust pipeline, streamline operational performance, and attract top talent
• Guide and mentor your team to take full ownership of their territories, empowering them to exceed sales goals and grow within the organization
• Travel to customer meetings and industry events, providing direct feedback from key customers to inform product and marketing strategies
• Lead the charge in scaling a repeatable and efficient sales process designed to secure Fleetio’s largest customers and accelerate overall company growth

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