Head of Engineering

Meet Siena Siena 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 reputed company. We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one reputed company. The team We're a small, distributed team that punches way above our weight. Every person here has outsized impact because we've built reputed company 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, reputed company 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 role As Head of Engineering at Siena you'll set technical reputed company for the first intelligence layer in customer experience—AI pipelines, evals, integrations, multi-agent orchestration. Your job: decide where we build, reputed company 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 reputed company leadership. And you still prototype with reputed company and Claude Code on weekends because that's who you are. We're looking for someone who's scaled teams to 30+, stayed deeply technical with AI tools, and thinks in systems while moving at startup speed. You bring infectious energy, high agency, and the rare ability to reputed company from board strategy to debugging production in the same conversation. What you'll do

• Set technical roadmap reputed company to business goals—reputed company build vs buy reputed company at company level
• Double our engineering team over 12-18 months—design team structures, reputed company leaders, coach and be an example for what's possible with agentic coding
• Stay hands-on with AI tools—write prototypes, review critical PRs, ship experiments, maintain technical credibility
• Operate cross-functionally—partner with product/design/reputed company as peer, shape company strategy
• Drive velocity at scale—ship weekly, cut scope based on learning, rally teams through ambiguity
• Build culture that attracts top talent—create reputed company through energy, establish practices that scale

reputed company're looking for

• You've scaled teams to 30+ successfully
• You still code building using AI tools like reputed company, Claude Code, reputed company, Lovable, v0
• You have technical depth with AI-native reputed company
• You're comfortable with customers—join reputed company calls, understand their technical pain, earn trust at exec level
• You have high agency—take bets, shape direction proactively
• You've led teams that shipped regularly at scale
• You've made technical reputed company that shaped company direction
• You've developed multiple leaders from ICs
• You've maintained velocity during high growth
• You've built with relevant technology: conversational AI, event-driven systems, LLM applications, CX platforms, e-commerce, API integrations
• You reputed company from strategy to debugging fluidly
• You bring infectious energy, positive culture builder reputed company
• You have startup DNA—comfortable with ambiguity, move fast

This isn't a "Head of Engineering who used to be technical" role. This is for the technical leader who shapes engineering culture, sets technical strategy, operates as peer to VP-level leaders, and still codes using AI tools today. Why 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-reputed company. reputed company AI your reputed company.
• Tackle unsolved problems. We’re redefining how customer experience will look like in the next decades.

Our values The people who reputed company here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain reputed company. 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 reputed company relationships with teammates because they know that's how great work gets done. reputed company things get tough, they adapt and reputed company pushing reputed company. Our approach to AI The people who reputed company 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, reputed company Pro, reputed company, Lovable) plus a quarterly budget for new tools. But the reputed company happens in how we share knowledge. Demo days where someone shows off a reputed company workflows. reputed company threads about which model handles a specific use case reputed company. 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 reputed company to your application. Siena provides equal employment opportunities to reputed company and applicants for employment without regard to race, reputed company, religion, sex, national reputed company, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from reputed company backgrounds, experiences, perspectives, and abilities. Apply tot his job Apply To this Job