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

You'll build the talent function from zero and own Siena's growth at series A. You'll sit with our founders and leadership team to shape what we hire for, when, and why — challenging role definitions before they hit the market, sequencing hires against business priorities, and making sure every hire we make is the right person at the right time. The strategic and the operational aren't separate tracks here — they're the same job, and you own both.

You deeply understand our product, our mission to build the intelligence layer for commerce, and what makes us different — because every candidate interaction is a signal of who Siena is. You'll design the systems, build the AI infrastructure, and set the standard for how Siena hires as we scale. If you're the kind who builds leverage instead of asking for headcount, this is your room to run.

You thrive when

• Selling the team and the trajectory when bigger companies are selling the brand and the package — and winning.

• Operating at the pace of high-growth startups — building structure while everything's still moving

• Figuring out what's broken in the hiring funnel and fixing it before it compounds

• You're the one setting the bar, not inheriting it — and you'd rather build the system than be handed a playbook

• Making a high-judgment call with incomplete information and being right more often than not

What you'll do

• Run full-cycle recruiting across engineering, product, operations, go-to-market, and leadership roles

• Own the entire talent function — strategy, execution, systems, outcomes

• Build and own the hiring plan in partnership with founders and leaders — translate business priorities into a sequenced recruiting roadmap and facilitate alignment when priorities conflict

• Design recruiting infrastructure that scales: scorecards, calibrated interview loops, pipeline analytics, documented processes

• Source and engage passive candidates for hard-to-fill and senior roles

• Know when to bring in external support and how to manage those partnerships effectively

• Build AI infrastructure that powers the hiring function — think Claude-based agents for intake, AI screeners generated from role packets, systems where each layer feeds the next

Who you are

You've built this before

• 7+ years in talent, with significant time as the first or sole talent hire at a scaling startup

• You've built or revamped a talent function from scratch — ATS selection, process design, scorecard frameworks.

• You've personally sourced and closed roles across all levels — from senior ICs to C-suite

• Experience hiring internationally across time zones — EOR structures, distributed teams, global comp benchmarking

You build systems, not just fill roles

• AI-native operator: you don't just use AI tools — you build AI systems. You've designed agents, automated pipelines, or built infrastructure where AI does the work, not just assists it

• Systems thinker — conversion rates, bottlenecks, feedback loops. When something breaks, you fix the system, not just the symptom

• Comfortable hiring across both technical and commercial roles

Do not apply if

• You've only operated within established talent functions and never owned one end-to-end

• You need clear structure and a defined career path to do your best work. This is pre-Series A — you're creating the structure

• You haven't personally closed a role in the last two years. Strategy without execution doesn't work at our stage

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 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 they build real relationships with teammates because they know that's 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. 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, 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 a clever workflows. Slack threads about which model handles a specific use case better. 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 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.