Director, AI Engineering - GTM Systems & Agents

Samsara (NYSE: IOT) is the pioneer of the Connected Operations™ Cloud, enabling physical operations industries—representing over 40% of global GDP—to harness Internet of Things (IoT) data.

Within Samsara, the Machine Learning, AI, Analytics & Data (MAAD) team builds intelligence engines that help our go-to-market teams work faster and make data-driven decisions. As Director, GTM AI Engineering, you will run the AI Engineering team powering Sales, Customer Success, Support, Enablement, and GTM leadership. This is a hands-on Director role where you will spend ~70% of your time prototyping AI agents, writing code, designing evals, and architecting shared AI platform capabilities, and ~30% leading the team, setting GTM AI strategy, and driving executive alignment.

Key Responsibilities

• Hands-on AI Prototyping & Delivery: Prototype, ship, and iterate on production-grade AI agents, copilots, and workflow automations for GTM workflows—taking tools from initial demo to live operational systems.
• Shared GTM AI Platform Architecture: Design and own the architecture of the shared GTM AI platform, including agent orchestration, LLM/tool gateways, identity/access layers, Model Context Protocol (MCP) servers, and SDK contracts across Salesforce, Slack, web apps, and Claude plugins.
• First-Class Evals Discipline: Establish evaluation frameworks for LLM and agent behaviors—designing golden datasets, LLM-as-judge pipelines, human review loops, and regression suites to audit quality over time.
• AI Strategy & Cost Management: Own model routing across vendors, per-user spend controls, and build-vs-buy evaluations for GTM tools; decide which prototypes move to the shared platform or retire.
• Field Advocacy & Adoption: Act as the primary advocate for AI across Sales, CS, and Support; conduct live demos, gather field feedback, and convert frontline reps into power users.
• Responsible AI & Safety: Implement least-privilege permissions, human-in-the-loop approval paths for CRM changes, and data privacy guardrails around customer data.
• Revenue-Critical Intelligence: Oversee predictive propensity modeling, forecasting signals, and CRM data-quality foundations consumed by sales leadership.
• People Leadership: Hire, develop, and retain a high-performing, inclusive AI engineering team (~30% of role).

Requirements

AI Engineering Depth & Technical Leadership

• 10+ years of progressive experience across software engineering, machine learning, data science, or data platforms, including demonstrated leadership experience. Active, regular coding practice is required.
• Hands-on experience building and shipping production LLM applications and agentic workflows (tool use, RAG, context engineering, and prompt routing).
• Production full-stack and cloud engineering experience (e.g., Python or TypeScript, AWS, Databricks).
• Practical experience designing and operating eval frameworks for LLM or agent systems (e.g., golden datasets, automated LLM-as-judge).
• Active daily use of AI coding assistants and agent harnesses in your own engineering workflow.
• Strong grounding in predictive modeling, analytics engineering, and cloud data architecture.
• Exceptional executive presentation and field communication skills—capable of demoing to a sales floor and presenting strategy to VPs.

Education & Work Logistics

• Bachelor’s degree in Computer Science, Data Science, Software Engineering, or equivalent relevant experience.
• Must reside in the United States.

Preferred Qualifications

• Prior experience building AI or decisioning platforms for GTM functions (Sales, Customer Success, Support, Marketing) in an enterprise SaaS ecosystem.
• Familiarity with GTM platforms (Salesforce, Gong, Gainsight, Zendesk) and connecting agents to them via MCP servers or API integrations.
• Hands-on experience with agent SDKs/harnesses (Claude Code, OpenAI Agents SDK, LangGraph) and eval/observability frameworks (Braintrust, MLflow).
• Experience managing AI inference spend, model routing, and operational cost controls at scale.

Total Rewards & Benefits

• Equity & Growth: Competitive base salary + initial RSU grant with no vesting cliff + ongoing refresh grants in a public technology company.
• Flexible Work & Stipends: Employee-led flexible remote model + dedicated professional development stipend.
• Comprehensive Healthcare: Premium medical, dental, and vision coverage options + generous parental leave plans.
• Culture & Belonging: Inclusive work culture guided by Samsara’s core principles (Focus on Customer Success, Build for the Long Term, Adopt a Growth Mindset).