Regional Sales Director, Commercial - West

Upwind Security

$130K — $180K *
Information Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of experience leading sales teams in SaaS or cybersecurity sectors
  • Proven track record of exceeding regional revenue targets
  • Strong sales experience in Cloud, Security, or DevOps markets
  • Expertise in recruiting and retaining high-performing sales talent
  • Experienced in managing complex, multi-threaded sales cycles
  • Familiarity with sales methodologies like MEDDPICC and pipeline management
  • Ability to effectively communicate with and influence C-level executives
  • Strong analytical skills with a focus on forecast accuracy and CRM best practices
  • Adaptable and collaborative, thriving in startup environments

Responsibilities

  • Build and scale a high-performing Commercial Account Executive team in the West region
  • Develop and implement a regional sales strategy that drives revenue growth
  • Coach and mentor sales team members throughout the sales cycle
  • Engage in and close high-value enterprise deals personally
  • Cultivate relationships with key stakeholders and C-level executives
  • Collaborate with cross-functional teams for alignment and growth
  • Implement a disciplined sales process to enhance pipeline management
  • Expand relationships with channel partners to stimulate growth
  • Provide data-driven insights and forecasts to senior leadership
  • Refine the go-to-market strategy based on customer feedback

Benefits

  • Health, dental, and vision insurance
  • 401(k) program with company matching
  • Generous paid time off and flexible scheduling
  • Professional development opportunities
  • Dynamic and inclusive company culture
Full Job Description
Description

About The Position

We are looking for a Regional Sales Director, Commercial - West to build, lead, and scale our Commercial sales team across the Western region (Rockies + West Coast). 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 in the Western United States.*

Responsibilities

  • Build, lead, and scale a high-performing team of Commercial 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 Commercial 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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