[Remote] Senior Manager, Engineering - AI & Automation

Note: The job is a remote job and is open to candidates in USA. Smartsheet is a company that empowers teams to automate processes and uncover insights. They are seeking a Senior Manager of Engineering for their AI & Automation team, responsible for leading engineers to deliver AI-powered capabilities rapidly, while partnering with product management and architecture teams.

Responsibilities

• 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

Skills

• 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
• 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
• Experience defining AI governance frameworks, citizen developer programs, or internal platform standards

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)

Company Overview