Head of Engineering

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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.

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 the 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’ll shape Siena’s technical strategy, influence product direction, build the culture, and operate as a peer to product, design, and revenue leadership. You will still prototype with Cursor and Claude Code on weekends because that’s who you are.

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 a 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

Why Siena?

Our Values

The 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 build real relationships with teammates. When things get tough, they adapt and keep pushing forward.

Our Approach to AI

The 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 writing. 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. Demo days, Slack threads, and shared knowledge keep the flow alive.

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.

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