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Role Description

The Director of Sales oversees the development and execution of strategic sales plans, manages vertical-specific sales teams, and ensures alignment with company goals and operational capacity. The Director of Sales plays a critical role in building and scaling high-performing sales teams, optimizing outbound and inbound sales processes, and supporting cross-functional collaboration across marketing, product, and operations.

This position may focus on a specific industry vertical or strategic initiative, such as selling into regulated industries or leading high-growth, best-in-class sales operations within the MSP space. All Directors of Sales are expected to maintain a strong command of the sales pipeline, coach and develop their team, and contribute to long-term revenue planning.

• Own all aspects of sales leadership, including forecasting, performance management, coaching, and hiring.
• Develop and implement targeted sales strategies tailored to industry verticals and buyer personas.
• Lead, manage, and develop a team of Account Executives, instilling a results-driven, high-accountability culture.
• Manage and iterate on commission plans, outbound cadences, and key sales processes.
• Drive new client acquisition in line with company growth targets; oversee the health of the sales pipeline and CRM accuracy.
• Work cross-functionally with marketing, product, and operations to ensure alignment and high-impact execution.
• Participate in and lead sales planning, including 1-year, 3-year, and 5-year sales growth initiatives.
• Analyze and refine sales playbooks based on real-time data, market shifts, and feedback from the field.
• Lead weekly sales retrospectives and quarterly business reviews to evaluate rep performance, deal velocity, and close rates.
• Ensure technology, documentation, and collateral are current and optimized to support the full sales cycle.
• Champion our culture, values, and operating system in all sales initiatives and leadership activities.
• Ensure compliance with industry standards, especially when engaging regulated customers (banking, finance, healthcare, etc.).

Qualifications

• Bachelor's degree in Business, Marketing, or a related field.
• 7+ years of progressive sales leadership experience, ideally in a Managed Services Provider (MSP) environment.
• Proven success in managing complex sales cycles with multi-level stakeholders, especially in regulated industries, a plus.
• Advanced understanding of sales technologies: CRM (HubSpot), forecasting tools, sequencing platforms, and analytics dashboards.

Benefits

• Medical, Dental, and Vision Insurance
• 401K Retirement Plan
• Minimum 4 Weeks of Paid Time Off (PTO)
• Birthday PTO
• Paid Holidays
• Paid Time Off for Volunteering
• Short-Term and Long-Term Disability Insurance
• Life Insurance
• Supplemental Insurance
• Employee Assistance Program