Regional Sales Director (Peninsula)

OverviewJoin to apply for theRegional Sales Director (Peninsula)role atWorkBoard . About WorkBoard WorkBoard is the pioneer inAI-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 DoingDelivering 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 ForA proven track record of enterprise selling where you’ve closed deals in the $100k to $500k range to consistently exceed 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 HaveExperience 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. Seniority levelDirector Employment typeFull-time Job functionSales and Business Development Industries Software Development#J-18808-Ljbffr

Created: 2026-02-20