Regional Sales Director (Peninsula)

Job Title: Regional Sales Director (Peninsula)

About WorkBoard

WorkBoard is a pioneer in AI-driven strategy execution solutions, empowering enterprises to align, measure, and achieve their most important outcomes.

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.

Responsibilities

• 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.

Requirements

• 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.