Senior Proactive Support Operations Specialist

Position Overview

We are looking for an Operations Specialist to join the Proactive Support organization and help us turn strategic priorities into effective, scalable execution.

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• Lead and coordinate cross-functional programs and operational initiatives from planning through execution, ensuring clear ownership, milestones, dependencies, and outcomes
• Support the organization's strategic planning and operating rhythm, including business reviews, program reviews, planning cycles, initiative tracking, and follow-up actions
• Partner with program owners and stakeholders to translate organizational priorities into actionable plans and drive progress against agreed outcomes
• Create visibility across programs and initiatives through effective tracking, reporting, documentation, and stakeholder communication
• Identify operational gaps, bottlenecks, and opportunities for improvement, and help design and implement practical, scalable solutions
• Develop and maintain processes, governance mechanisms, templates, and operational resources that improve consistency and efficiency across the organization
• Coordinate stakeholders across teams, geographies, and functions, proactively identifying dependencies, risks, and areas requiring alignment or escalation
• Support the definition and tracking of KPIs, success measures, and program outcomes, using data and qualitative insights to identify trends and areas for improvement
• Prepare materials and insights for leadership discussions and business reviews, helping ensure decisions and actions are clearly captured and followed through
• Support change management and adoption of new processes, tools, and ways of working across the organization
• Manage multiple priorities simultaneously, adapting quickly as business needs and organizational priorities evolve

• Experience in Operations, Program Management, Project Management, Business Operations, Customer Success Operations, or a related field
• Strong program and project management skills, with demonstrated experience coordinating multiple initiatives and stakeholders
• Excellent organizational skills and ability to bring structure and clarity to ambiguous or complex work
• Strong communication and stakeholder management skills, with the ability to work effectively across different teams and levels of an organization
• Experience improving processes and implementing new ways of working
• Ability to identify risks, dependencies, and blockers and proactively drive them toward resolution
• Strong analytical mindset and experience using data and insights to support decision-making and measure outcomes
• Comfortable working independently, taking ownership, and operating in a fast-moving, evolving environment

• Experience working within a global technology, SaaS, Customer Success, or customer-facing organization
• Experience supporting organizational planning, business reviews, governance, or portfolio/program management
• Experience working within a complex, matrixed organization and influencing stakeholders without direct authority
• Familiarity with project/program management and collaboration tools such as Smartsheet, Microsoft 365, or similar platforms
• Experience supporting change management or organizational transformation initiatives

• Create clarity and momentum around important organizational initiatives
• Make it easier for leaders and program owners to understand progress, risks, dependencies, and required decisions
• Help teams move from discussion and planning into execution
• Build simple, scalable operational processes rather than adding unnecessary complexity
• Develop strong relationships across Proactive Support and become a trusted partner to program owners and stakeholders
• Proactively identify problems and opportunities rather than waiting to be asked
• Balance attention to detail with an understanding of the bigger organizational objectives

We're looking for someone who enjoys making things work better. You don't need to have all the answers from the beginning. We value curiosity, ownership, collaboration, and the ability to take an ambiguous…