Senior Manager, Engineering - AI & Automation

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday. Corporate Systems Engineering builds and operates the software platforms, integrations, and automations that power Smartsheet’s core business functions across Finance, Sales/GTM, and People & Culture. Our team owns mission-critical systems and workflows that enable how the company hires, sells, bills, pays, reports, and scales. We operate at the intersection of software engineering, enterprise platforms, and business-critical data, treating internal systems with the same rigor, reliability, and product mindset as customer-facing software. The AI & Automation team is our frontier - we're building the next generation of how employees interact with enterprise systems using agentic AI, large language models, and cloud-native automation. This isn't traditional IT. This is product-minded engineering applied to internal tools, with the mandate to fundamentally change how our employees work. As a Senior Manager, Engineering (AI & Automation), you will lead a team of engineers focused on shipping AI-powered capabilities to employees on a rapid, iterative cadence. This is a hands-on, tech-leaning leadership role where the primary measure of success is delivery velocity — how quickly and effectively your team puts Claude, AWS Bedrock, and other AI tools into the hands of employees to make them measurably more efficient. You will partner closely with Product Management to own the automation roadmap and with Architecture and Data teams to shape our internal AI infrastructure. This full-time position reports to the Sr. Director, Development and can be located in our Bellevue, WA office, or you may work remotely from anywhere in the US where Smartsheet is a registered employer. You Will • Lead and grow a team of 4-8 automation engineers across US and offshore locations, responsible for designing, building, and operating automation solutions across Finance, Sales/GTM, People & Culture, and shared corporate workflows. • Serve as a hands-on technical contributor (player/coach) — prototyping AI agents, reviewing architecture, and shipping features alongside your team, particularly in early-stage capabilities where speed matters more than delegation. • Ship incremental AI-powered features on a regular cadence using Claude, AWS Bedrock, and our internal platform. Your team's primary output is employee-facing AI capabilities - agents that can read, write, and act across enterprise systems through natural language. • Partner with Product Management to prioritize the automation roadmap, balancing quick wins that demonstrate value with foundational platform investments. You own delivery; the PM owns prioritization. • Design and operate LLM-powered automation pipelines - intelligent search, retrieval-augmented generation, and decision workflows that allow employees to programmatically interact with system data through natural language. • Partner with Data Engineering, Architecture, and platform teams to design and evolve our internal knowledge graph, RAG infrastructure, and enterprise search capabilities. • Own the internal AI governance model for corporate systems, including the citizen developer framework - the guardrails, enablement resources, quality standards, and compliance controls that allow employees across the business to build with AI safely. This is a leadership responsibility, not a documentation exercise • Drive operational excellence across the automation portfolio: sprint execution, CI/CD practices, reliability, SLAs, and data-driven engineering metrics. Build a team that ships predictably and sustainably. • Stay at the frontier of AI/automation technologies and bring that perspective into how we work. Challenge existing approaches, advocate for modern patterns, and help the broader organization rethink legacy integrations through an AI-first lens. • Contribute to multi-year strategies for automation and AI governance, lifecycle management, platform consolidation, and deprecation of legacy technologies. You Have • 10+ years experience in software, automation, or systems engineering roles • 4+ years management or technical leadership experience with player/coach characteristics • Hands-on experience building with LLMs - whether that's agentic workflows, retrieval pipelines, prompt engineering at scale, or enterprise AI features. You've shipped something real, not just experimented. • Integration development skills using iPaaS or custom code connecting enterprise systems via APIs • Experience building or operating enterprise automations against systems such as Workday, NetSuite, Salesforce • Experience with AWS or another cloud environment for automation workloads (Bedrock, SNS, SQS, Lambda, Step Functions, EventBridge) • Experience partnering with Product Managers or equivalent business prioritization models • Experience supporting data programs, data governance and tooling to support data initiatives • Experience implementing or consuming LLM-based workflows, retrieval pipelines, or enterprise search • Experience defining execution rituals, backlog management, outcome-based tracking without PM intermediaries • Experience building and mentoring engineering talent • Experience defining AI governance frameworks, citizen developer programs, or internal platform standards (preferred) • A degree in Computer Science, Engineering, or a related field or equivalent practical experience • Legally eligible to work in the U.S. on an ongoing basis 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 $205,000 - $257,500 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, and India. 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.