Siena AI

• Own technical resolution end-to-end • You take full ownership of Tier 2+ escalations. • You debug API integrations independently: auth failures, webhook issues, data sync gaps, rate limiting, intermittent failures, provider-specific limitations. • You diagnose and resolve customer-side JavaScript issues. • You triage AI and chatbot behavior — wrong answers, workflow misconfiguration, hallucination patterns. • You run diagnostic SQL on data discrepancies, missing records, and report mismatches. • After every Tier 2+ resolution, you ask if a pattern can move back to Tier 1. • You build and maintain internal documentation for common failure modes. • You own complex technical issues directly with customers. • You manage expectations confidently through multi-step debugging processes.

• Run product education for the Siena team. Every release lands with a session, a doc, and a demo that the company actually walks away knowing. • Run customer workshops and recurring product sessions. One use case at a time. Real depth, real outcomes. • Build the customer onboarding path. From signed contract to first value, repeatable across every segment. • Onboard every new hire. They ramp through your program, and they're productive faster because of it. • Build the demo library. Live, recorded, vertical-specific, persona-specific. Sales pulls from it. Customers learn from it. • Build Siena Academy. Curriculum, certifications, learning paths. Internal and external. The credential brands earn to show they know Siena. • Build the Siena community. The recurring spaces, events, and rituals where customers, partners, and operators come to learn from us and each other. • Educate the market. Open courses, public content, frameworks others adopt. The Academy becomes the category-defining resource on CX AI. • Arm sales with demos, narratives, and product positioning. Demo scripts, vertical storylines, the words that close deals. • Build the AI systems that scale all of the above. You teach the agents how to teach. Your taste is the final filter.

• You will own how Siena grows. New customers, existing customers, and everything between them. • Demand creation, product launches, brand, content, expansion, retention as a marketing motion. The full surface area of how the world finds Siena and how Siena keeps the customers it earns. • You work directly with both founders. You build the function. You build the team. • New customer acquisition. Demand creation across every channel that works. Brand, content, social, events, paid, partnerships. The pipeline that fuels Series A and beyond. • Existing customer growth. Expansion, adoption, retention as a marketing problem. Customer marketing, co-marketing, references, community. • Product launches end to end. Every release becomes a market moment. Positioning, messaging, distribution, the works. • Category leadership. Siena is creating the category of CX operating system for brands. You own how that category gets defined and adopted. • Brand and momentum. The campaigns, content, and presence that make Siena the first name in CX AI. • The growth system. You build the AI agents and workflows that let one person move like ten. You orchestrate. Your taste is the final filter.

• Embed with strategic accounts as the technical member of the deployment pod - alongside a Deployment Manager and/or Forward Deployed PM • Diagnose and resolve technical blockers: integration failures, Zendesk configuration issues, automation logic gaps, data sync problems • Build account-specific automations and integrations that aren't yet supported out of the box • Own the technical setup of new accounts during onboarding - integrations live, data flowing, first automations configured • Surface patterns across accounts to the engineering and product teams: recurring technical issues that should become platform features rather than one-off fixes • Contribute to shared technical documentation and deployment playbooks that reduce ramp time for every future account • Participate in technical scoping during late-stage sales - help the team understand what's realistic before contracts are signed

• Own technical account health: diagnose automation performance issues, configure improvements, and drive resolution rates without always pulling in engineering • Be the primary point of contact for your accounts - customers know you by name and trust that you'll bring them clarity. • Run regular business reviews with customer stakeholders - bring data, tell the story, and drive clear next steps • Partner with the deployment team during onboarding to ensure the handoff is clean and the account is set up to succeed • Translate what you hear from customers into structured product feedback the team can act on

• Own deployments from zero to live - kick-off, automation setup, stakeholder alignment, and hitting the metrics that matter. • Co-lead strategic accounts with senior team members, taking on responsibility progressively as you ramp. • Apply your CX ops knowledge to diagnose why accounts are stuck: helpdesk configuration, ticket routing gaps, automation logic, escalation failures - and drive the fix. • Keep every account you touch moving: daily updates, proactive escalations, clear documentation of progress and blockers. • Manage customer expectations with confidence: hold timelines, push back when scope creeps, and keep relationships intact when things get hard. • Shadow and support senior team members for the first 30 days, then take the lead on accounts. • Feed operational patterns back to the product team: you see problems across accounts before anyone else does.

• Own AI agent outcomes for strategic accounts end-to-end - automation rates, resolution rates, time-to-value • Deploy agents, identify what's blocking progress, then build the platform fix so the next account benefits • Work directly with enterprise CX leaders to design AI transformation roadmaps - and execute them • Turn deployment insights into platform capabilities. What you learn in the field shapes what we build next • Build and improve agent capabilities that work across platforms - support, shopping, reviews, voice, social • Design evaluation systems: 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 communities

• Own the weekly cadence for Channels and Analytics. • Work with PMs and engineering leadership to surface and sequence priorities - including the ones nobody has written down yet. • Help organise backlogs and bring structure to teams operating in a fast-moving, low-process environment. • Unblock engineers proactively. Identify the constraint before it becomes an escalation. • Write and maintain technical debt plans with engineers, not for them. • Act as a second thinker on integration strategy and capacity planning. • Improve the things that slow good engineers down. • Run 1:1s that leave engineers with clearer thinking, not just status logged. Deliver hard feedback directly. Have it land, not bruise. Help develop senior engineers who want to grow - including coaching engineers who have ambitions toward management. • Act as a backup hiring partner: help run loops, hold the bar, partner with recruiting.

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.

• Design, build, and maintain scalable features across the full stack (frontend, backend, and infra). • Collaborate with Product to break down scope into iterative, high-impact releases. • Integrate cutting-edge LLM capabilities into real enterprise workflows. • Work on an AI-first product, integrating cutting-edge LLM capabilities into enterprise customer support workflows. • Solve complex engineering challenges, from optimizing API performance to refining microservices architecture. • Maintain and improve our cloud infrastructure (AWS) with a DevOps mindset. • Exercise high agency and ownership—taking initiative, making decisions, and driving ideas to production.