Regional Sales Director (Peninsula)

About WorkBoard 

WorkBoard is the pioneer in AI-driven strategy execution solutions, empowering enterprises to align, measure, and achieve their most important outcomes. With our platform, organizations can operationalize strategy in real-time, foster alignment across teams, and accelerate growth. Our customers include some of the world’s most innovative companies across technology, financial services, healthcare, and more. 

We’re backed by top-tier investors and led by a diverse, mission-driven team that’s passionate about redefining how organizations execute strategy at scale. At WorkBoard, you’ll have the opportunity to join a fast-growing, category-defining company where your work directly impacts how leaders shape the future. 

The Role 

We are seeking a Regional Sales Director with an entrepreneurial spirit and a proven track record in B2B software sales. This is a unique opportunity to sell into a new category and shape how global enterprises think about strategy execution. Your ability to open doors, educate executives, and build trust with key decision-makers will be crucial to both your success and WorkBoard’s category leadership. 

What You’ll Be Doing 

• Delivering on your revenue targets by: 
  • Identifying and engaging high-potential target accounts across multiple industries. 
  • Developing innovative outreach strategies to secure meetings with C-suite and senior executive stakeholders. 
  • Articulating our unique value proposition, educating the market on how AI transforms strategy management and execution. 
  • Building a robust pipeline through prospecting, networking, and multi-channel outreach. 
  • Developing and delivering compelling presentations to executive prospects, demonstrating how WorkBoard drives measurable outcomes. 
• Managing the full sales cycle with a consultative, solution-focused approach tailored to the challenges of selling in an emerging category. 
• Partnering with internal teams to shape tailored solutions for each customer’s strategic needs. 
• Establishing trust-based relationships with decision-makers, positioning yourself as a strategic advisor. 
• Capturing and sharing market feedback to help refine our category narrative and product strategy. 

What We’re Looking For 

• A proven track record of enterprise selling where you’ve closed deals in the $100k to $500 range to consistently exceeded your quarterly and annual revenue targets.  
• 7–10 years of successful B2B enterprise software sales experience, preferably in new market or category-creation environments. 
• Exceptional prospecting skills with the ability to secure meetings with C-level executives. 
• Strong business acumen and the ability to articulate how AI impacts strategic business outcomes. 
• Entrepreneurial mindset with the ability to thrive in ambiguity and fast-paced growth. 

Nice to Have 

• Experience launching new products or breaking into new markets.
• Familiarity with strategy execution concepts and how they apply in business.
• Background in early-stage startup environments with a record of sales success.