Product Manager, Agent Autonomy

Meet Siena

Siena is the Agent of Record for CX, built for consumer brands like Spanx, FIGS, Brooklinen, and Grüns.

It runs as a connected multi-agent stack on top of a shared intelligence layer: agents that sell, support, listen, handle social and voice across the entire customer journey, turning every conversation into signal you can act on.

The team

We are a small, fully distributed, global team. We have built leverage into how we work, which is what lets a team this size move at the speed we do.

We hire athletes. Everyone here owns real outcomes, defaults to writing over meetings, communicates with directness, and acts the moment they see something worth acting on. Low ego, high standards, fast clock.

If you want to set the bar rather than follow one, keep reading.

The Role

Siena needs a PM to own autonomy: the product surface where our agents act without a human in the loop. You'll decide where autonomy is safe to expand, give customers real visibility into what's automated versus escalated, and run the experiments that make autonomous resolution better over time. You're a strong problem solver first, and you've been a Product Manager in CX, ecommerce, helpdesk, or AI automation.

What You'll Do

• Own autonomy end to end: define where agents can act without a human in the loop, and push that boundary as trust and evals allow

• Build and ship the systems that make autonomous resolution measurably better: evaluation suites, automated testing, performance monitoring that catches issues before customers do

• Give customers real-time visibility into coverage: what's automated, what's escalated, and why, so trust in autonomy compounds instead of eroding

• Design and run journey-level A/B tests across agent flows, and use the results to decide what ships next

• Own onboarding and automation so customers reach full autonomous coverage in days, not weeks

• Run full launch cycles for autonomy features: internal testing, early access, GA, with customer enablement through webinars, docs, and training

• Demo autonomy wins to customers directly and co-sell alongside sales

• Act as forward-deployed PM when needed: sit with customers, scope live, and move fast from insight to shipped improvement

Who You Are

The Bar: If you're missing any of these, this isn't the role for you.

• You're a strong problem solver, full stop

• 3+ years working as a Product Manager in CX, ecommerce, helpdesk, or AI automation

• AI-native: you build with Claude, Cursor, v0, or similar as a daily part of how you work, not just something you've tried

Strong Signal: Not dealbreakers, but what separates a good hire from a great one.

• Experience running structured experiments or A/B tests to improve a product metric, not just intuition-led changes

• Technical fluency: you can scope webhook systems, OAuth flows, and complex integrations yourself

• Customer confidence: you thrive talking with customers, running demos, and co-selling alongside sales

Nice to Have: Bonus, not required.

• Experience building trust or visibility features (dashboards, coverage reporting, status pages) for a product customers rely on

• Background implementing or rolling out complex systems for enterprise customers

Not a Fit If:

• You want a narrowly scoped PM seat with a fixed roadmap handed to you

• You're not comfortable being customer-facing or getting on a call to demo your own work

• You'd rather stay behind the product than own the messy, ambiguous parts

Why Siena?

Real ownership. You will own problems, not tasks, with the autonomy to solve them your way and the trust to do it without a manager in your inbox.

Work that ships and matters. What you build reaches real consumer brands fast.

A category we are creating. The Agent of Record is new ground, with unsolved problems and cutting-edge models, not a crowded field to compete in.

A team that respects your judgment. Globally distributed, async-first, low bureaucracy. We hire adults and treat you like one.

Great salary plus equity or stock grants. Own a piece of what you build.

Learning budget. If you are growing, so are we.

AI-fluency by default. Few places will push your work with production AI further or faster.

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.

How we hire

We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at talent@siena.cx.

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.