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.

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.

The Sr. Director, Workforce Transformation is accountable for delivering measurable, structural change to the business — not just managing a program. The expectation is that this role produces outcomes that are visible and supports Smartsheet's capacity to scale with AI:

• →Amplify Capacity through AI: Identify and execute on opportunities to grow output and capability faster than we grow our cost base — translating AI adoption into tangible productivity gains
• →Deep partnership with Finance and People & Culture: Partner with Finance and People & Culture to build a globally optimized talent model — strategically aligning talent to where Smartsheet is growing, including deepening our capabilities in key markets in a way that is financially disciplined and operationally sound
• →Role architecture that scales: Partner with People & Culture to inform and evolve job architecture in a way that reflects the realities of an AI-augmented workforce — ensuring roles are positioned for the next three to five years, not the last three to five
• →Faster organizational response to AI launches: Reduce the lag between product capability releases and internal role adoption — ensuring the organization captures the value of new AI tools quickly and systematically
• →Workforce risk mitigation: Provide leadership with clear, data-driven visibility into workforce risk — skills gaps, role evolutions, retention exposure — so decisions are proactive rather than reactive

• 12-15+ years of experience in management consulting, organizational transformation, or workforce strategy, with significant time spent at a top-tier consulting firm (McKinsey, Bain, BCG, or equivalent)
• Deep understanding of AI and its future implications for organizational design, workforce planning, and job architecture
• Demonstrated experience leading large-scale organizational or workforce transformation initiatives, including stakeholder management, change communications, and executive reporting
• Strong financial acumen — able to build workforce models, partner with Finance, and frame workforce decisions in terms of cost, efficiency, and ROI
• Exceptional cross-functional leadership skills — this role will work across Business Operations, People & Culture, Finance, and Product and requires the credibility and influence to lead without direct authority
• Outstanding communication and executive presence — able to synthesize complex, ambiguous situations into clear, compelling recommendations for senior audiences
• Bachelor's degree required; MBA or advanced degree strongly preferred

• Experience in a PE-backed or sponsor-backed environment, with familiarity operating at the pace, rigor, and accountability PE ownership demands
• Familiarity with global talent models and geographic staffing strategy, including COE structures
• Background in AI enablement, digital transformation, or future-of-work strategy — particularly in organizations actively deploying AI/ML into core products or operations
• Prior experience in SaaS or enterprise software companies that have undergone significant business model or go-to-market transitions

• Direct report to the Chief Business Officer with visibility and access at the most senior levels of the organization
• A blank-sheet-of-paper opportunity to build a new function and define what workforce transformation looks like at Smartsheet
• The chance to lead the most strategically important organizational initiative at an AI-forward, PE-backed enterprise SaaS company
• A clear mandate with defined scope, measurable outcomes, and the organizational support to execute at pace
• Unique positioning at the intersection of Business Operations, People & Culture, Finance, and Product — with the cross-functional authority to drive real change
• Direct partnership with the Business Operations function, which sits within the same CBO remit, providing immediate access to executive communications, strategic planning, and cross-functional visibility that accelerates the pace and impact of transformation work

At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together.

Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, and India. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information. 

If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.

#LI-Remote