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Meet Siena

Siena is the first intelligence layer for customer experience. Were 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 doesnt just automate support; it powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human.

Were transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.

The team

Were a small, distributed team that punches way above our weight. Every person here has outsized impact because weve built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with.

If youre excited about building something that doesnt exist yet, keep reading. Were building agents that dont just respond to customers—they remember them, learn from every interaction, and connect experiences across channels.

About The Role

You’ll lead the teams building the first intelligence layer for customer experience. This spans AI pipelines, evals, integrations, and multi‑agent orchestration. Your job: turn ambitious product bets into reliable systems while keeping the team energized, aligned, and focused.

Were looking for a leader with a builders DNA who approaches the role like a founding team member would. Youll shape product decisions, drive technical strategy, empower your team to execute on high‑impact projects, and play a pivotal role in scaling the team.

You’re not just excited about software—youre obsessed with building the best agentic operating system for customer experience.

What You’ll Do

• Build and lead high‑velocity teams that ship fast and with polish.
• Be deeply technical and hands‑on. Read the PRs, write prototypes, jump into the weeds. Leadership is an amplifier, not a step back.
• Turn raw ideas into working systems. Even if you have to duct tape the first version together.
• Rally your team through ambiguity, setbacks, and tough customer asks. Run through walls when needed.
• Push for clarity, focus, and high energy in every sprint. Drive urgency without burning people out.
• Drive alignment on the roadmap and become an expert on customer needs related to the product areas your team owns.
• Spend time with customers and engineers alike—digging into pain points, testing assumptions, and improving the craft.
• Coach, mentor, and build a team of curious, scrappy, driven engineers—people who want to grow fast and build great things.
• Foster an AI‑first culture by showing, not telling, what AI enables for builders.
• Ensure engineering cycles produce real, reliable impact: accuracy improvements, integrations, and agent capabilities that delight customers.
• Translate Siena’s vision into execution your team can rally behind.
• Grow engineering talent into leaders, making Siena’s engineering team a career destination.

What We’re Looking For

• You’ve successfully led product‑focused engineering teams in high‑performing organizations that shipped real impact.
• You’ve written code at a high level, and you still love to get your hands dirty. You view leadership as an amplifier, not a step back.
• Bias for action and scrappiness. You dont over‑optimize for process. You optimize for velocity, customer value, and learning.
• You deeply care about the customer experience. You think about UX, APIs, performance, edge cases, and joy.
• You ask “why” obsessively, and you push yourself (and your team) to learn constantly.
• You build trust, give direct feedback, and create space for engineers to thrive.
• You have experience partnering with recruiting teams to drive effective and fair hiring processes. You realize that recruiting is a large (and important!) part of your role.
• You have experience with systems complexity: LLMs, APIs, integrations, data pipelines, or event‑driven products.
• Proven ability to drive clarity and culture across distributed teams.

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 youre 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 thrive here are curious, customer‑obsessed, and take ownership without being asked. They fix problems first and explain later. Theyre 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 real relationships with teammates because they know thats how great work gets done. 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. Theyve 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, 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 clever workflows. Slack threads about which model handles a specific use case better. Learning from each others 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 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.

Seniority level

Mid‑Senior level

Employment type

Full‑time

Job function

Engineering and Information Technology

Industries

Technology, Information and Internet

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