Regional Sales Director – Enterprise

This is a fully remote position, open to applicants in Florida, +2 more states.

📋 Description

• Build, manage, and grow a high-performing team of Enterprise Account Executives throughout the Southeast region.

• Develop and implement a regional sales strategy to surpass revenue objectives and ensure steady pipeline development.

• Mentor, coach, and nurture AEs through all phases of the sales cycle, enhancing overall team effectiveness and execution.

• Actively engage in and assist in closing strategic, high-value enterprise transactions.

• Foster robust relationships with C-level executives and key stakeholders within target accounts.

• Collaborate cross-functionally with Marketing, Sales Engineering, Customer Success, and Channel teams to ensure alignment and drive revenue growth.

• Implement a disciplined sales process, including pipeline management, forecasting accuracy, and qualification methodologies (e.g., MEDDPICC).

• Build and enhance relationships with channel partners and ecosystem participants to expedite regional growth.

• Provide regular, data-driven insights and forecasts to executive leadership.

• Contribute to shaping and refining Upwind’s go-to-market strategy based on customer and market feedback.

⛳️ Requirements

• Proven experience in leading and scaling Enterprise sales teams within high-growth SaaS or cybersecurity firms.

• A consistent record of exceeding regional or team revenue targets.

• Strong expertise in selling to enterprise clients in Cloud / Security / DevOps sectors.

• Demonstrated capability to recruit, hire, and retain top-tier sales talent.

• Experience in managing complex, multi-threaded sales cycles and closing strategic deals.

• Profound understanding of sales methodologies (e.g., MEDDPICC) and disciplined pipeline management practices.

• Strong executive presence with the ability to engage and influence C-level stakeholders.

• Data-driven approach with a commitment to forecast precision and CRM integrity (SFDC).

• Highly collaborative, adaptable, and comfortable working in a fast-paced, early-stage startup environment.

• Comprehensive understanding of cloud security concepts, technologies, and the market landscape.

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance.

• Generous paid time off and holidays.

• Opportunities for professional development and career advancement.

• A vibrant, inclusive company culture that values innovation and teamwork.