Regional Sales Director; Peninsula

Position: Regional Sales Director (Peninsula)
Overview

Join to apply for the Regional Sales Director (Peninsula) role at Work Board.

About Work Board

Work Board 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  Work Board, 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 Work Board’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 Work Board 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 $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 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.

Seniority level

• Director

Employment type

• Full-time

Job function

• Sales and Business Development

• Industries

• Software Development

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