Sr. Director, Workforce Transformation

Smartsheet•Bellevue, WA

2d•$285,000 - $315,000•Remote

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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. Serve as a strategic thought partner and change catalyst to C-suite leaders, bringing the gravitas, data, and conviction to challenge the status quo and push the organization toward bolder, faster adoption of AI-enabled operating models. Build the muscle for sustained, ongoing change — not one-time programs.
Executive Reporting Serve as a credible, trusted voice on workforce strategy at the executive level. Provide regular, data-driven updates to the CBO and Senior Leadership Team on transformation progress, workforce metrics, risk, and opportunity. Establish reporting frameworks that demonstrate measurable impact to the Senior Leadership Team and the Board.

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
US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
US employees receive 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)