Senior Manager, IT Delivery

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. We are seeking a Senior Manager, IT Delivery - a technical, hands-on "player-coach" who will serve as the strategic execution engine for our Information Technology department. Reporting to the Senior Manager of IT Systems, you will bridge the gap between our high-performing engineering leaders and teams and evolving business needs. This role is designed for a proactive decision-maker who deeply understands system architecture and can navigate ambiguity to drive high-visibility, cross-functional initiatives across the IT ecosystem. The Team & Impact: You will manage a single Project Manager and support five specialized units: MDM, SaaS, Network, ServiceNow DevOps, and Compliance (UAR Coordination). Your success is measured by your ability to; unblock technical bottlenecks, onboard, consolidate and integrate tooling, find efficiencies in processes and tech, proactively identify and address end user pain points, and act as a credible, highly communicative face for IT across the enterprise. A day in the life (Responsibilities) • Hands-On Delivery: Lead the end-to-end execution of critical IT systems initiatives (e.g., SailPoint/Identity Governance integrations and deployments, new tool deployment, User Access Reviews, and major system integrations). • Ecosystem Integration & Decision Making: Drive holistic decisions across IT domains by understanding how core platforms (such as Identity, Service Management, and Collaboration tools) integrate and operate together. • Roadmap & Analytical Reporting: Partner closely with IT Leaders to Define success metrics for IT programs and build dashboards to track enterprise-wide impact, regularly publishing post-mortems and trend analyses to inform future technical and strategic decisions. • IT Enablement & User Adoption: Drive enterprise-wide user adoption for the tech stack. Create and scale training programs, publish technical release notes, and maintain a centralized documentation repository. • Strategic Liaison: Serve as the highly communicative primary point of contact between IT domains (Systems, Security, Infrastructure) and external business stakeholders, translating complex technical infrastructure into clear business value. What you'll need to thrive (Requirements) • Experience: 7+ years of IT enterprise system ownership, ideally in environments of 7,000+ users. • Core Systems Knowledge: Demonstrated, hands-on familiarity with core IT industry tools, specifically ServiceNow, SailPoint (or similar IGA platforms), Okta, AWS, Google Workspace, and Atlassian (Jira/Confluence), MDM and Security Agent tooling . You must understand how these tools operate and integrate at a foundational level. • Ambiguity Navigation & Decision-Making: Proven ability to drive projects forward and make strategic decisions when there is a lack of defined structure or resources. • Matrix Leadership: Strong history of driving cross-functional teams that do not directly report to you and unblocking technical dependencies. • Exceptional Communication: Outstanding written and verbal communication skills; a polished presenter who can confidently and professionally distill complex technical concepts into accessible, clear updates for non-technical stakeholders. • Pragmatic Execution: A focus on rolling up your sleeves to drive execution, prioritizing real-world outcomes over rigid adherence to project management methodologies. What will help you stand out (Nonessential Skills/Nice to Haves) • Background in IT Business Operations or IT Service Management (ITSM). • Experience utilizing data analytics tools (e.g., Snowflake