Role Description 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 Qualifications - 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 Benefits - 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.