Job Title

Head of Engineering at Siena AIScroll down to find an indepth overview of this job, and what is expected of candidates Make an application by clicking on the Apply button.Join to apply for the Head of Engineering role at Siena AI.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 touchpointfrom 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 customersthey remember them, learn from every interaction, and connect experiences across channels.About The RoleAs Head of Engineering at Siena you'll set technical vision for the first intelligence layer in customer experienceAI pipelines, evals, integrations, multi-agent orchestration. Your job: decide where we build, what we buy, how we scale. You're shaping Siena's technical strategy, influencing product direction, building the culture. You operate as peer to product, design, and revenue leadership. And you still prototype with Cursor and Claude Code on weekends because that's who you are.What you'll doSet technical roadmap aligned to business goalsmake build vs buy decisions at company levelDouble our engineering team over 12-18 monthsdesign team structures, develop leaders, coach and be an example for what's possible with agentic codingStay handson with AI toolswrite prototypes, review critical PRs, ship experiments, maintain technical credibilityOperate crossfunctionallypartner with product/design/revenue as peer, shape company strategyDrive velocity at scaleship weekly, cut scope based on learning, rally teams through ambiguityBuild culture that attracts top talentcreate momentum through energy, establish practices that scaleWhat we're looking forYou've scaled teams to 30+ successfullyYou still code building using AI tools like Cursor, Claude Code, Codex, Lovable, v0You have technical depth with AInative fluencyYou're comfortable with customersjoin enterprise calls, understand their technical pain, earn trust at exec levelYou have high agencytake bets, shape direction proactivelyYou've led teams that shipped regularly at scaleYou've made technical decisions that shaped company directionYou've developed multiple leaders from ICsYou've maintained velocity during high growthYou've built with relevant technology: conversational AI, eventdriven systems, LLM applications, CX platforms, ecommerce, API integrationsYou zoom from strategy to debugging fluidlyYou bring infectious energy, positive culture builder mindsetYou have startup DNAcomfortable with ambiguity, move fastWhy SienaMeaningful 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.AIfluency. Make AI your second nature.Tackle unsolved problems. Were redefining how customer experience will look like in the next decades.Our valuesThe people who thrive here are curious, customerobsessed, and take ownership without being asked. They fix problems first and explain later. They're direct about feedbackboth giving and receiving itbecause they care more about getting things right than being polite. They maintain high standards while moving at startup speed, and they build real relationships 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 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 workflow. Slack threads about which model handles a specific use case better. Learning from each other's AI workflows. At Siena, were not just looking for people who can do a job. Were looking for people who want to break boundaries, create the future, and reshape industries. If thats 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. xjdpvnf We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.