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. ... (truncated, view full listing at source)