Job Description
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, Business Transformation, you will establish the program management infrastructure, leading the most critical initiatives, and building the organizational capability to deliver at PE pace. Your first major initiative is AI-enabled Workforce Transformation, one of the company's highest-priority organizational initiatives. From there, you will have the opportunity to take on additional cross-functional transformation work. 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 business transformation 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 Program Architecture & Governance Build and run the operating infrastructure that keeps transformation moving — standing up program management frameworks, establishing steering committees, defining decision rights, and creating the measurement systems that track progress against outcomes. You design the governance model, set the operating rhythm, and hold the accountability structure that ensures initiatives don't just launch but land. Workforce Strategy & Planning For the Workforce Transformation project, define and execute a comprehensive 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 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 planning decisions. Role Redefinition Work closely with People & Culture and functional leaders to proactively shape jobs 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. Change Management Champion and drive organizational change management strategies and communications, helping Smartsheet's team 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 strategy at the executive level. Provide regul