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 human.
We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.
The team   We'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 role   As Head of Engineering at Siena you'll set technical vision for the first intelligence layer in customer experience—AI 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.
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 zoom from board strategy to debugging production in the same conversation.
What you'll do      Set technical roadmap aligned to business goals—make build vs buy decisions at company level

Double our engineering team over 12-18 months—design team structures, develop 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/revenue 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 momentum through energy, establish practices that scale

What we're looking for      You’ve scaled teams to 30+ successfully

You still code building using AI tools like Cursor, Claude Code, Codex, Lovable, v0

You have technical depth with AI-native fluency

You’re comfortable with customers—join enterprise 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 decisions 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 zoom from strategy to debugging fluidly

You bring infectious energy, positive culture builder mindset

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-fluency. Make AI your second nature.

Tackle unsolved problems. We’re redefining how customer experience will look like in the next decades.

Our values   The people who…