Sr. Director, Workforce Transformation

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday. Smartsheet is a leading enterprise platform for dynamic work, empowering organizations to plan, execute, and report on work at scale. Backed by multiple private equity firms, Smartsheet operates with the rigor, discipline, and growth orientation of a world-class PE-backed SaaS company. We are at a pivotal moment — accelerating our AI capabilities, evolving our operating model, and building the organizational infrastructure to scale intelligently. The Opportunity Smartsheet is in the midst of a profound product and business transformation. The company’s AI roadmap is fundamentally reshaping how Smartsheet delivers value. These innovations aren’t just changing the product; they’re reshaping the work itself — across every function, from professional services to customer success to engineering. As Sr. Director, Workforce Transformation, you will own an incredibly strategic organizational question facing Smartsheet today: how do we evolve our organizational model in response to AI? This is a newly created, first-of-its-kind role at Smartsheet, built to ensure that as our AI product capabilities advance, our organization is ahead of it — not reacting to it. This role reports directly to the Chief Business Officer and operates at the intersection of AI strategy, people, financial planning, and organizational design. It is not an HR role. It is not a change management role. It is not a Product or Technology role. It is a transformation executive role that requires the analytical rigor of a management consultant, the organizational fluency of a business leader, and the strategic vision to see around corners in a rapidly evolving AI landscape in order to continue empowering Smartsheet as an enterprise market leader. This is an individual contributor role with outsized strategic influence. The right candidate is a corporate athlete — someone who can learn fast, operate across functions, and drive enterprise-wide change at PE pace. What You Will Own Workforce Strategy Planning Define and execute a comprehensive workforce transformation strategy that prepares Smartsheet for an AI-enabled future, spanning role redesign, capability building, and organizational readiness across all functions. Partner with Finance, People Culture, and business unit leaders to build forward-looking workforce planning models — covering headcount, skills, cost structure, and organizational ratios — that anticipate how AI adoption will reshape team structures and skill requirements over 12–36 month horizons. Translate roadmap milestones into actionable workforce planning decisions. Role Redefinition Work closely with People Culture and functional leaders to proactively redefine job architecture and responsibilities as the product evolves — ensuring role design stays ahead of capability launches rather than responding to them after the fact. Lead the effort to rapidly redesign roles as AI automates, augments, and transforms existing workflows, collaborating with Product, Engineering, and IT teams to translate technical roadmaps into workforce implications. Geographic Talent Strategy Partner with HR and functional leaders to design a sustainable global talent model. Change Management Design and lead organizational change management frameworks and communications that enable Smartsheet's workforce to navigate transformation with clarity and confidence — addressing stakeholder alignment, resistance management, and employee engagement. ... (truncated, view full listing at source)