Regional Director - West

Upwind Security

• $160K — $200K *
US-AnywhereRemote in San Francisco, CA
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • Proven experience leading Enterprise sales teams in high-growth SaaS or cybersecurity companies.
  • Track record of exceeding revenue targets on a regional or team basis.
  • Strong background in sales to enterprise customers within Cloud, Security, or DevOps environments.
  • Demonstrated ability to recruit and retain top sales talent.
  • Experience in complex, multi-threaded sales cycles and strategic deal closures.
  • Deep understanding of sales methodologies like MEDDPICC and pipeline management.
  • Strong executive presence and ability to influence C-level stakeholders.
  • Data-driven mindset focused on forecast accuracy and CRM maintenance.
  • Adaptable and collaborative in fast-paced, early-stage startup environments.
  • Strong understanding of cloud security concepts and market landscape.

Responsibilities

  • Build, lead, and scale a high-performing team of Enterprise Account Executives in the West region.
  • Develop and execute a sales strategy to exceed revenue targets and maintain strong pipeline generation.
  • Coach and mentor AEs through the sales cycle to enhance overall team performance.
  • Engage directly in closing high-value enterprise deals and strategic opportunities.
  • Establish robust relationships with C-level executives and key stakeholders in target accounts.
  • Collaborate with Marketing, Sales Engineering, Customer Success, and Channel teams to drive revenue alignment.
  • Implement a disciplined sales process, including management of pipeline, forecasting, and qualification methods.
  • Expand relationships with channel partners to accelerate regional growth.
  • Provide data-driven insights and forecasting to executive leadership.
  • Refine Upwind's go-to-market strategy based on market and customer feedback.

Benefits

  • Opportunity to lead a critical sales function within a rapidly growing cloud security startup.
  • Engage directly with C-level executives and influential stakeholders.
  • Collaborative environment with cross-functional alignment.
  • Focus on talent development and building a high-performing team.
  • Potential to shape company strategy based on insights and market trends.
Full Job Description
We are looking for a Regional Sales Director, Enterprise - West To build, lead, and scale our Enterprise sales team across the West region.. This is a critical leadership role responsible for driving revenue growth, developing top-performing talent, and establishing Upwind as a category leader in cloud security. You will play a key role in shaping our go-to-market strategy, closing strategic deals, and building a high-performance, customer-first sales culture. *This is a field leadership role open to qualified candidates located the west. CA highly preferred. Responsibilities
  • Build, lead, and scale a high-performing team of Enterprise Account Executives across the West region
  • Develop and execute a regional sales strategy to exceed revenue targets and drive consistent pipeline generation
  • Coach, mentor, and develop AEs through all stages of the sales cycle, elevating overall team performance and execution
  • Personally engage in and help close strategic, high-value enterprise deals
  • Establish strong relationships with C-level executives and key stakeholders within target accounts
  • Partner cross-functionally with Marketing, Sales Engineering, Customer Success, and Channel teams to drive alignment and revenue growth
  • Drive a disciplined sales process, including pipeline management, forecasting accuracy, and qualification methodologies (e.g. MEDDPICC)
  • Build and expand relationships with channel partners and ecosystem players to accelerate regional growth
  • Provide regular, data-driven insights and forecasting to executive leadership
  • Help shape and refine Upwind's go-to-market strategy based on customer and market feedback
Requirements
  • Proven experience leading and scaling Enterprise sales teams in high-growth SaaS or cybersecurity companies
  • Track record of consistently exceeding regional or team revenue targets
  • Strong background selling to enterprise customers in Cloud / Security / DevOps environments
  • Demonstrated ability to recruit, hire, and retain top sales talent
  • Experience leading complex, multi-threaded sales cycles and closing strategic deals
  • Deep understanding of sales methodologies (e.g. MEDDPICC) and disciplined pipeline management
  • Strong executive presence with the ability to engage and influence C-level stakeholders
  • Data-driven mindset with a commitment to forecast accuracy and CRM hygiene (SFDC)
  • Highly collaborative, adaptable, and comfortable operating in a fast-paced, early-stage startup environment
  • Strong understanding of cloud security concepts, technologies, and market landscape

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