Head of Operations

Overview
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
As Head of Operations at Siena AI, you/'ll own our execution engine- operationalizing cross-functional initiatives, building scalable systems, and ensuring our fast-growing AI company runs like clockwork. You/'ll turn strategy into action while leading our People Ops and overseeing recruiting efforts to fuel continued growth.

What You'll Do

Operationalize and align multiple initiatives across Product, Engineering, Marketing, and Customer Success teams.

Oversee critical cross-functional projects from a program management perspective, ensuring clear accountability and execution.

Build and run our OKR framework and operating cadence to keep all teams focused and aligned.

Oversee recruiting operations for key roles and lead our People Ops team to scale talent acquisition, build company culture, and create systems that support team growth.

Manage legal and compliance initiatives and standards in collaboration with our legal team.

Own vendor procurement and operational infrastructure projects to support company growth (e.g., access management systems, security tooling).

Who You Are

Proven Operations Leader - 7+ years in operational roles at fast-growing tech companies or management consulting, with a track record of driving company-wide initiatives.

Strong Program Manager - Demonstrated success overseeing complex, cross-functional projects with clear accountability and results.

Recruiting & People Ops Experience - Experience designing structured hiring processes, improving time-to-hire, building scalable people programs, and developing company culture systems.

Vendor & Compliance Management - Experience with vendor procurement, access management systems, and supporting legal/security compliance initiatives.

Strategic & Hands-On - Able to design high-level systems while also diving into execution details to get things done.

Systems Builder - Experience creating processes and operating rhythms that scale as companies grow rapidly.

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.

We are committed to 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.

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