Regional Sales Manager, Mid-Market

Position Overview

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Fleetio is seeking a Regional Sales Manager, Mid-Market to drive sales growth in a significant market. This role involves leading a Mid-Market Sales Team to capture a large addressable market of businesses. Fleetio is a modern software platform for fleet operations management, operating in a rapidly growing transportation technology sector. The company has secured substantial funding and is on an upward trajectory, also being a founding member of the Rails Foundation.

About Fleetio

• Fleetio overview video: https://www.youtube.com/watch?v=IlvIbwZT3oU
• Our careers page: https://www.fleetio.com/careers

Role Description

Reporting to the Director of Mid-Market Sales, you will be a key member of the sales leadership team. Your responsibilities include mentoring Mid-Market Account Executives, achieving accurate forecasts, defining and tracking KPIs, and fostering a coaching culture for continuous improvement. You will collaborate with leaders in sales, marketing, business operations, and sales enablement to shape team strategy.

Your Impact

• Manage and oversee the daily activities and output of your team, including prospecting, funnel management, forecasting, and negotiation.
• Lead a team of individual contributors to enhance performance by driving key weekly activities.
• Align sub-department execution with broader division goals and objectives.
• Continuously review and recommend process or strategy changes to improve sub-department performance.
• Motivate and empower the team to take ownership of their territories 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 to achieve top objectives.
• Lead people management for the sub-department, including hiring, off-boarding, performance management, and compensation.
• Cultivate and manage a compelling career path with promotional and backfill opportunities.

Your Experience

• Minimum of 3 years in a sales leadership role within a B2B SaaS company.
• Proven success managing a team quota of $2M+.
• Consistent track record of exceeding assigned team revenue objectives.
• Proven track record and strategy for scaling outbound sourced ARR.
• Demonstrated success in coaching and developing team members.
• Intermediate business acumen, including forecasting and budget management.
• Data-driven decision-making skills.
• In-depth understanding of sales processes and product knowledge.
• Ability to identify and attract top talent.
• Experience in transparent performance management.
• Strong negotiation skills (external prospects and internal stakeholders).
• Inspirational communication skills to motivate team performance.
• Driven front-line management ability to connect with direct reports and inspire performance.
• Ability to build trust with the team, cross-functional partners, peer leaders, and senior leadership.

Benefits

• Health Insurance: Multiple health/dental coverage options (100% coverage for employee, 50% for family).
• Vision Insurance: Provided.
• Stock Options: Incentive stock options.
• Retirement: 401(k) with a 4% match.
• Paid Time Off (PTO): 4 weeks, increasing at year two.
• Holidays: 12 company holidays + 2 floating holidays.
• Parental Leave: 16 weeks paid for birthing parent, 4 weeks paid for non-birthing parent.
• Flexible Spending Accounts (FSA) & Health Savings Accounts (HSA): Options available.
• Disability Insurance: Short and long-term disability (short-term is 100% paid).
• Community Service Funds: Provided.
• Professional Development Funds: Provided.
• Wellbeing Fund: $150 quarterly.
• Business Expense Stipend: $125 quarterly.
• Technology: Mac laptop and new hire equipment stipend.
• Office Amenities: Fully stocked kitchen with a variety of drinks.