Director of Business Planning & Strategic Initiatives - Office of the CPTO (Remote Eligible)

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. Smartsheet is seeking a dynamic, operationally focused leader to join our team to lead the Office of the Chief Product and Technology Officer (CPTO). As the right-hand to the CPTO, you will play a key role in running the 650-person team’s operations, driving key initiatives to support our transformation strategy, and forging relationships across Smartsheet to ensure seamless execution and operations. Reporting to the CPTO, this is a high-visibility, high-accountability, and high-velocity role. The successful candidate will use their emotional intelligence and business acumen to inform strategic priorities and collaborate across the organization to accomplish our big, audacious goals. Smartsheet is at a pivotal moment in our history as we transition our value proposition, our GTM operations, and our entire product lineup into the agentic era to solidify our position as the leader in Enterprise. This is a remote eligible position and you may work remotely from anywhere in the US where Smartsheet is a registered employer. You Will: Annual Planning and Transformation Operations: Partner with the CPTO to build the org-wide 3-year strategic plan, focused on product adoption, revenue retention & growth, and customer value delivery aligned to the GTM strategy. Provide lift to Executives where needed on strategic initiatives. Serve as business leader in the annual strategic and financial planning process, connecting the various streams of work occurring across all product functions and partnering with Finance and GTM organizations. Identify and manage critical planning decisions, cross-functional dependencies, and any gaps that arise through the planning process. Partner with Revenue Operations on OKR and initiative tracking and progress through the year to support accountability across the business. Facilitate alignment and collaboration amongst the Executive Leadership Teams. Leadership Team Operations: Serve as a trusted thought partner and force multiplier to the leadership team, ensuring their time, attention, and decision-making are focused on the highest-leverage priorities. Own the leadership operating rhythm — staff meetings, leadership offsites, QBRs, and board or executive committee touchpoints — ensuring each is well-structured, purposeful, and followed up on. Establish and manage a leadership operating system, including an operational cadence for the CPTO and the leadership team, overseeing operational rituals/routines such as team meetings, offsites, monthly and quarterly reviews. Help prepare for board presentations, investor briefings, and executive leadership forums, including developing the narrative, structuring the materials, and synthesizing supporting data. Research, understand, and respond to the needs of global product and tech leaders related to coordination, communication, and reporting to create a cohesive organization (without constraining functional velocity). Work with key Finance and Revenue Operations partners to track budget and headcount planning. Communications and Culture: Build and maintain team-wide communications rituals and content, i.e., team intranet, monthly newsletter, town-halls, and more, to foster visibility, alignment, and connection. Develop and publish regular cadence of intra-R&D and company-wide blogs and presentations to drive shared understanding of R&D strategy. Monitor organizational health signals — team sentiment, retention risk, cross-functional friction — and surface them proactively with recommended actions. Craft critical communications/presentations for the CPTO’s team cascades, speaking engagements, team intranet, and organization-wide communications for internal and external branding, engagement and alignment. Strategic Cross Functional Initiatives: Opportunistically run point on cross-functional projects. Run governance on change management planning for transformation initiatives, including establishing a standardized approach to change management across teams. Work in partnership with functional and technical program management teams to execute project/initiative plans. You Have: Minimum 10+ years experience in strategy, operations or program management in a SaaS business. Management consulting or equivalent experience is required. MBA preferred. Successful track record in building, scaling, mobilizing, and refining strategy and associated programs/initiatives for complex businesses, ideally in a go-to-market function. Excellent communication and stakeholder management skills, capable of building relationships at every organizational level. Experienced with organizational design, organizational behavior, leadership development and/or team development. Meticulous attention to detail and the capacity to juggle multiple projects simultaneously. Proficient in data analysis and adept at using metrics to guide decision-making and continuous improvement. Travel average 25% time, up to 50% time on occasion. Primarily domestic, some international. Current US Perks & Benefits: Employer subsidized medical/vision and dental coverage 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) Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity. US Base Salary Pay Range $223,750 — $261,250 USD Get to Know Us: 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. Equal Opportunity Employer: 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, India, and Singapore. 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