Product Manager, AI Agent Deployment

Meet Siena. Siena is the first intelligence layer for customer experience. We are 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 are transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.

The team is 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.

As a Product Manager, AI Agent Deployment you’re embedded with strategic accounts, owning their deployment outcomes while building platform capabilities. Forward-deployed PM meets technical account ownership. You deploy agents and turn those insights into product improvements that scale. You’re energized by the loop: deploy agents → drive outcomes → identify gaps → build platform improvements → repeat.

Who You Are

• 3+ years in PM, solutions engineering, implementation, TAM, customer success engineering, or product ops
• Experience with technical products and enterprise customers
• AI-native mindset. You live in Claude Code, Cursor, and max out your LLM limits
• You can scope webhooks, OAuth flows, and complex integrations
• You ship features, write docs, run demos, and measure what matters
• You’ve lived the problems customers are trying to solve. You know what "great CX" looks like
• You can diagnose whether problems are technical, operational, or stakeholder-related and prioritise accordingly
• You are comfortable advising CX leaders on organisational design, process optimisation, and transformation strategy
• Ability to work in North American time zones is a must

What You’ll Do

• Own agent outcomes for strategic accounts end-to-end.
• Deploy AI agents, drive automation rates, identify what’s blocking progress, then build the platform fix
• Work directly with enterprise CX leaders to design AI transformation roadmaps that you’ll help execute
• Turn deployment insights into platform capabilities that help every customer, not just the one you learned from
• Build new agent capabilities that work seamlessly across platforms
• Design evaluation systems that make our agents continuously smarter. QA suites, automated testing, performance monitoring
• Run full launch cycles from internal testing to GA, including customer enablement
• Demo your own products and co-sell alongside sales. You’ll be known by name in our customer Slack communities

What You’ll Get

• Competitive salary, equity, flexible remote work
• Premium AI tools (ChatGPT, Claude, Perplexity Pro, Cursor) plus quarterly budget for new tools
• Clear growth pathways into deeper specialisation or team leadership

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 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.

We provide equal employment opportunities to all employees and applicants for employment without regard to race, colour, 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.