Product Manager, Autonomy (AI Agent of Record) at 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, handling sales, support, social, and voice interactions across the entire customer journey, turning every conversation into actionable signal.

What You’ll Own

You’ll be the Product Manager for autonomy—the product surface where agents act without human intervention. Your role involves:

• Defining where agents can operate independently, expanding boundaries as trust and evaluations allow
• Building and shipping systems that improve autonomous resolution, including evaluation suites, automated testing, and performance monitoring
• Providing customers with real-time visibility into coverage, explaining what’s automated, escalated, and why
• Designing and running journey-level A/B tests across agent flows to inform product decisions
• Ensuring customers achieve full autonomous coverage in days, not weeks, through streamlined onboarding and automation
• Managing full launch cycles for autonomy features, including internal testing, early access, and GA rollouts with customer enablement via webinars, documentation, and training
• Demonstrating autonomy wins directly to customers and co-selling alongside the sales team
• Acting as a forward-deployed PM, engaging with customers to scope live issues and deliver rapid improvements

Who You Are

The Bar: If you lack any of these, this role isn’t for you.

• You’re a strong problem solver—no exceptions
• 3+ years of experience as a Product Manager in CX, ecommerce, helpdesk, or AI automation
• You’re AI-native: integrate tools like Claude, Cursor, or v0 daily—not just as a novelty

Strong Signal: Not dealbreakers, but what sets great hires apart.

• Experience running structured experiments or A/B tests to improve product metrics, not just intuition-led changes
• Technical fluency to scope webhook systems, OAuth flows, and complex integrations
• Customer confidence: thrive in demos, co-selling, and direct customer interactions

Nice to Have: Bonus, not required.

• Experience building trust or visibility features (e.g., dashboards, coverage reporting, status pages) for mission-critical products
• Background implementing complex systems for enterprise customers

Not a Fit If:

• You prefer a narrowly scoped PM role with a fixed roadmap
• You’re uncomfortable being customer-facing or demoing your work
• You’d rather stay behind the product than tackle ambiguity and messy problems

Why Siena?

Real ownership: You’ll solve problems, not tasks, with autonomy and trust to execute your way.

Work that matters: Your contributions reach real consumer brands quickly.

Cutting-edge innovation: The Agent of Record is a new frontier with unsolved challenges and AI-driven solutions.

Respect and trust: Globally distributed, async-first, and low-bureaucracy. You’re treated like an adult.

Compensation: Great salary plus equity or stock grants. Own a stake in what you build.

Learning budget: Invest in your growth, and we’ll invest in yours.

AI-fluency: Few places push AI integration further or faster.

Our Values

We thrive on curiosity, customer obsession, and ownership. You fix problems first, explain later. Feedback is direct—because getting things right matters more than politeness.

We maintain high standards while moving at startup speed, building real relationships to deliver great work.

When challenges arise, we adapt and push forward.

Our Approach to AI

We treat AI as an extension of ourselves. Everyone uses premium tools (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) and a quarterly budget for new tools. Knowledge-sharing is key—demo days, Slack threads, and learning from each other’s AI workflows.

We’re not just looking for job-doers; we’re looking for boundary-breakers who want to reshape industries.