Meet SienaSiena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions.Siena doesn't just automate support; it powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human. We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.The teamWe're a small, distributed team that punches way above our weight. Every person here has outsized impact because we've built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with.If you're excited about building something that doesn't exist yet, keep reading. We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels.About the roleYou'll lead teams building and deploying AI agents for customer experiences. This isn't a traditional engineering manager role as you'll both build platform capabilities (AI pipelines, evals, integrations) and own deployments for strategic customers.We're looking for a leader with a builder's DNA who approaches the role like a founding team member would. You're obsessed with building the best agentic operating system for customer experience and proving it works by making customers wildly successful.What you'll doBuild and deploy production-grade AI agents: You'll lead a team of engineers building and deploying highly performant, reliable AI agents for strategic customers. These are scalable systems handling millions of customer conversations in production. You'll ensure technical excellence, operational reliability, and high customer impact. You'll be hands-on: meet customers, read PRs, build integrations, jump into customer issues when needed.Own outcomes for customers: You'll deploy agents for a portfolio of strategic accounts and own their success. This means driving automation rates up, improving quality, managing escalations, and running customer reviews. You'll coordinate with Sales, Implementation, and Customer Success teams to deliver results. Your customers should be growing and staying with Siena.Shape the platform based on deployment learnings: Your team's work with customers will guide platform priorities. You'll surface what's breaking, what's missing, and what would unlock more value. Build evals and measurement frameworks to prove what works in production. Turn deployment insights into product requirements and work with Product, Design, and Engineering teams to shape the roadmap.Lead and grow your team: Rally your team through ambiguity, setbacks, and tough customer asks. Push for clarity, focus, and high energy in every sprint. Drive urgency without burning people out. Coach and mentor engineers who want to grow fast and build great things. Partner with recruiting to hire exceptional talent.What you'll bringExperience leading engineering teams that build and scale end-to-end production systemsStrong technical problem-solving skills and ability to guide teams through ambiguous, fast-changing environmentsDeep understanding of AI/ML systems—ideally agent orchestration, prompt engineering, RAG pipelines, or evaluation frameworksA leadership style that blends high standards with empathy, fostering both speed and qualityProven ability to work closely with customers and translate business needs into technical deliverablesYou measure success by customer outcomes, not just features shippedExcellent communication skills across technical and non-technical audiencesEven better if you haveExperience building or deploying AI/LLM systems in production at scaleBackground as a founder, engineering lead, or startup builder with high ownership and urgencyFamiliarity with modern agent tooling: eval frameworks, LangChain, observability toolsWhy Siena?Meaningful impact. Your work directly shapes our product and company.Globally distributed team working at the bleeding edge of CX and AI.Great salary plus the opportunity for equity or stock grants.Learning budget. If you're growing, so are we.The thrill of building something new. Join us at a stage where your contributions matter most.AI-fluency. Make AI your second nature. Tackle unsolved problems. We’re redefining how customer experience will look like in the next decades.Our valuesThe people who thrive here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain later. They're direct about feedback—both giving and receiving it—because they care more about getting things right than being polite. They maintain high standards while moving at startup speed, and they build real relationships with teammates because they know that's how great work gets done. When things get tough, they adapt and keep pushing forward.Our approach to AIThe people who thrive here treat AI like a natural extension of themselves. They've built their own ecosystem of agents - some for research, others for debugging, writing, analysis, or writing code. They know which AI works best for what problem.Everyone gets premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools. But the magic happens in how we share knowledge. Demo days where someone shows off a clever workflows. Slack threads about which model handles a specific use case better. Learning from each other's AI workflows.At Siena, we’re not just looking for people who can do a job. We’re looking for people who want to break boundaries, create the future, and reshape industries. If that’s you, we look forward to your application.Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.