Senior Director, Transformation & Business Operations

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 to customers. These innovations aren’t just changing the product; they’re reshaping the work itself — particularly in the Customer Excellence organization which includes professional services, customer success, customer experience and customer support.  

This is one of the most consequential roles in the Customer Excellence organization. The Senior Director, Transformation & Business Operations helps the CCO operate at full leverage across the business by aligning priorities and driving transformation initiatives.  This is not a scheduling or logistics role. The person in this seat translates the CCO’s vision into an operating rhythm, establishes the programmatic infrastructure to drive transformational initiatives, and facilitates change management.   

What You'll Own

Chief of Staff to the CCO

• Serve as a trusted thought partner and force multiplier to the CCO, ensuring their time, attention, and decision-making are focused on the highest-leverage priorities
• Own the CCO's operating rhythm — staff meetings, leadership offsites, QBRs, and board or executive committee touchpoints — ensuring each is well-structured, purposeful, and followed up on
• Prepare the CCO for board presentations, investor briefings, and executive leadership forums, including developing the narrative, structuring the materials, and synthesizing supporting data
• Act as a proxy for the CCO in cross-functional forums when appropriate, representing the CE organization's priorities and driving decisions forward
• Manage high-priority special projects on behalf of the CCO that require senior judgment and confidentiality
• Monitor organizational health signals — team sentiment, retention risk, cross-functional friction — and surface them proactively with recommended actions

Business Performance & Insights

• Own the CE organization's performance management framework — defining the KPIs, OKRs, and leading indicators that reflect the health of the business across CS, PS, Support, and CX programs
• Build and maintain the executive dashboards and reporting cadences the CCO uses to run the business and communicate performance to the C-suite and board
• Translate complex, multi-dimensional performance data into clear, compelling narratives that drive decisions — not just reports that describe what happened
• Lead the CE organization's annual planning process in partnership with the CCO, and Finance including headcount modeling, investment prioritization, and goal-setting alignment
• Identify performance trends, risks, and opportunities ahead of the leadership team and bring forward pointed recommendations.

CE Business Transformation  

• Lead Customer Excellence Transformation Initiatives — the program infrastructure responsible for identifying, designing, and executing the strategic change initiatives that evolve how the CE organization operates
• Define the methodology for how transformation initiatives are scoped, resourced, governed, measured, and closed
• Own the CE transformation roadmap — a living view of the cross-functional change programs underway, their interdependencies, and their expected business impact
• Assess the role of AI in strategically enriching, enhancing, and reshaping existing workflows
• Lead change management on major CE initiatives, ensuring that program design accounts for how people and teams actually adopt change, not just what the org chart says should happen
• Partner with the VP of Customer Experience & Scaled Execution, the Senior Directors of CS and PS programs, and Support leadership to identify where process, tooling, or structural changes are needed and build the case for investment

Cross-Functional Change Management  

• Serve as the connective tissue between the CCO's office and the broader CE leadership team — ensuring alignment on priorities, surfacing conflicts early, and creating the conditions for fast, effective decision-making
• Build and maintain strong partnerships with Finance, Sales, Product, and People teams to ensure the CE organization's initiatives are coordinated with broader company priorities
• Drive accountability across CE program owners by establishing clear decision rights, escalation paths, and communication standards
• Offer insights, data, and conviction to inspire a move toward faster, more confident adoption of AI-enabled operating models and workflows across Customer Excellence

What You Will Bring

• 10+ years of progressive experience in Customer Success, Professional Services, business operations, strategy, or management consulting — with meaningful exposure to enterprise SaaS
• Demonstrated experience operating as a Chief of Staff, Strategy Lead, or senior business partner to a C-level executive — you know what it takes to make an executive and a leadership team operate at their best
• Exceptional analytical and storytelling ability — you can work from raw data to board-ready, insights-driven narrative
• Experience building or leading strategic programs or large-scale transformation initiatives in a go-to-market/post-sale organization
• Strong financial acumen — able to build post-sale workforce models, partner with Finance, and frame strategic decisions in terms of cost, efficiency, and ROI
• Unusually strong judgment: you regularly handle sensitive information, navigate ambiguity, and make calls in the absence of perfect data
• Executive presence and credibility — you can represent the CCO's perspective in a room, hold your own with peers and senior stakeholders, and influence without direct authority.  You are able to synthesize complex, ambiguous situations into clear, compelling recommendations for senior audiences.  
• High organizational EQ — you understand the informal dynamics of an organization as well as the formal ones, and you factor both into how you operate
• Bonus: experience in a high-growth SaaS company scaling a Customer Experience or Go-to-Market function through a significant inflection point

Why This Role

The Customer Experience organization is at a pivotal moment — building new program capabilities, scaling execution, and operating with increasing visibility at the board and executive level. The CCO needs a trusted partner who can absorb complexity, generate clarity, and drive outcomes. This role is for someone who thrives at the intersection of strategy and execution, is energized by working at the center of a high-performing organization, and wants the scope and proximity to leadership that comes with being the person the CCO depends on most.