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Overview

Meet Siena—an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences, voice, and social media interactions. Siena powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human. We are transforming how businesses understand and connect with their customers, turning every interaction into intelligence that improves future experiences.

About the Role

As Head of Engineering at Siena you will set the technical vision for our first‑intelligence layer in customer experience. You will decide where we build, what we buy, and how we scale. You will shape Siena’s technical strategy, build culture, and operate as a peer to product, design, and revenue leadership.

What youll do

• Set the technical roadmap aligned with business goals and make build‑vs‑buy decisions at company level.
• Double our engineering team over 12‑18 months—design team structures, develop leaders, coach, and lead by example.
• Stay hands‑on with AI tools: prototype, review critical PRs, ship experiments, and maintain technical credibility.
• Partner with product, design, and revenue as a peer, shaping company strategy.
• Drive velocity at scale: ship weekly, cut scope based on learning, rally teams through ambiguity.
• Build a culture that attracts top talent—create momentum through energy and establish practices that scale.

What were looking for

• Scaled teams to 30+ successfully.
• Still code using AI tools like Cursor, Claude Code, Codex, Lovable, v0.
• Technical depth with AI‑native fluency.
• Comfortable with customers—join enterprise calls, understand pain points, earn trust at exec level.
• High agency—take bets, shape direction proactively.
• Led teams that shipped regularly at scale.
• Made technical decisions that shaped company direction.
• Developed multiple leaders from ICs.
• Maintained velocity during high growth.
• Built with relevant technology: conversational AI, event‑driven systems, LLM applications, CX platforms, e‑commerce, API integrations.
• Zooms from strategy to debugging fluidly.
• Brings infectious energy and a positive culture builder mindset.
• Has startup DNA—comfortable with ambiguity, moves fast.

Why Siena?

• Meaningful impact—your work directly shapes product and company.
• Globally distributed team working at the bleeding edge of CX and AI.
• Great salary plus equity or stock grant opportunities.
• Learning budget to support growth.
• The thrill of building something new at a stage where contributions matter most.
• AI fluency—make AI your second nature.
• Opportunity to tackle unsolved problems and redefine customer experience.

Our values

We thrive on curiosity, customer obsession, ownership, and direct feedback. We fix problems first, maintain high standards while moving fast, and build real relationships across teams—because great work requires collaboration.

Our approach to AI

We treat AI as a natural extension of ourselves, building an ecosystem of agents for research, debugging, writing, analysis, and coding. We provide premium AI accounts and a quarterly budget for new tools, and regularly share AI workflows and model insights with the team.

Equal Opportunity Statement

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.