Sr. Director, Workforce Transformation

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 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 shape job architecture and responsibilities as the product evolves — ensuring role design precedes capability launches rather than responding to them after the fact. Champion the initiative to strategically adapt roles as AI enriches, enhances, and reshapes existing workflows, partnering with Product, Engineering, and IT teams to translate technical roadmaps into exciting workforce opportunities.

Geographic Talent Strategy Partner with People & Culture and functional leaders to design a sustainable global talent model. 

Change Management Champion and drive organizational change management strategies and communications, helping Smartsheet's workforce embrace transformation with clear understanding and enthusiasm. This involves fostering strong stakeholder collaboration, proactively addressing concerns, and boosting employee engagement. Act as a trusted strategic advisor and catalyst for positive change with C-suite leaders, offering insights, data, and conviction to inspire a move toward faster, more confident adoption of AI-enabled operating models. Cultivate the internal capacity for sustained, positive evolution, moving beyond one-off initiatives.

Executive Reporting Serve as a credible, trusted voice on workforce strategy at the executive level. Provide regular, data-driven updates to th