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 commun…