[Hiring] Sr. Director, Workforce Transformation @Smartsheet

Role Description

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
• The strategic vision to see around corners in a rapidly evolving AI landscape

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.

Qualifications

• 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
• 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
• Outstanding communication and executive presence
• Bachelor's degree required; MBA or advanced degree strongly preferred

Requirements

• Workforce Strategy & Planning: Define and execute a comprehensive workforce transformation strategy that prepares Smartsheet for an AI-enabled future.
• Role Redefinition: Work closely with People & Culture and functional leaders to proactively redefine job architecture and responsibilities.
• 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.
• Executive Reporting: Serve as a credible, trusted voice on workforce strategy at the executive level.

Benefits

• Medical/vision and dental coverage options for full-time employees
• 401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)
• Monthly stipend to support your work and productivity
• Flexible Time Away Program, plus Sick Time Off
• 12 paid holidays per year
• Up to 24 weeks of Parental Leave
• Personal paid Volunteer Day to support our community
• Opportunities for professional growth and development including access to Udemy online courses
• Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
• Teleworking options from any registered location in the U.S. (role specific)