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 anchor on billing and invoicing — owning the day-to-day so the team can focus on complex cases and strategic work. From there, you'll operate as a generalist across compliance, legal intake, vendor management, and cross-functional programs.

The work is detail-heavy and high-stakes. A missed invoice, an overlooked contract clause, or an incomplete audit trail has real consequences — for customers, for the business, for the team. But it's also high-leverage: every loop you close frees the team for bigger bets.

This is an early-career role. We're open to exceptional new grads and candidates with 1-3 years of experience — what matters is raw aptitude, ownership instinct, and the ability to learn fast.

What you'll do

Own day-to-day billing and invoicing operations — issuing invoices, monitoring usage, drafting customer billing comms, and supporting dispute resolution
Assist with legal and compliance operations — contract intake, RFPs and security questionnaires, audit cycles, and policy hygiene across the team
Manage vendor operations and equipment inventory — from new tool requests and renewals to spend reconciliation and team equipment
Support cross-functional programs and strategic initiatives — audit prep, tooling migrations, and documentation that keeps the team running
Partner closely with Operations leadership on ad-hoc projects that scale with the company

Who you are

Detail-obsessed and systems-minded — you break messy problems into steps, owners, and deadlines, and actually close the loops
AI-curious and resourceful — you've built AI into how you think and work, whether through your job, side projects, or how you organize your own life
Comfortable with dense material — contracts, policies, spreadsheets, and dashboards don't intimidate you; you orient quickly and flag what you don't understand
Strong communicator — concise, warm, and structured, with the judgment to know when to flag, fix, or ask
Trustworthy and discreet — you handle sensitive information with care, own open threads without being asked, and have patience for ambiguity without tolerance for stagnation

Nice to have

B2B SaaS experience, especially CX, fintech, or AI
SOC 2, GDPR, or ISO 27001 audit-adjacent exposure
Paralegal or legal-ops background
FinOps, RevOps, or usage-based billing experience
Working fluency in Linear, Notion, HubSpot, or similar ops tools

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.