Siena AI

• Own end-to-end product launches - external market releases and internal team education - with full positioning, enablement, and amplification. • Manage complete customer success story lifecycle from identification through interviews, content creation, legal approvals, and distribution. • Build and run Siena Academy, creating curriculum that drives customer adoption and product value. • Create competitive intelligence system including battlecards, takedown decks, and positioning frameworks that help sales win. • Develop ROI calculators and business case materials that articulate value differentiation. • Build visual asset library with case studies, one-pagers, before/after comparisons, and templates sales can use immediately. • Establish tight feedback loops with sales, CS, and product to understand which assets drive pipeline and close deals. • Track marketing asset usage, pipeline impact, win rates, and revenue attribution to optimize what's working.

• Own a portfolio of strategic accounts ($100K+ ARR), driving retention, expansion, and executive relationships • Build stakeholder maps: who matters, where decisions get made, where Siena can expand next • Lead multi-team expansion, beyond the CX buying center into Marketing, Returns, E-commerce, Operations • Run executive-level strategic conversations that move contracts and direction — this is about commercial outcomes, not calendar touch-points • Partner with AEs on multi-team commercial expansion; partner with PMs to translate account needs into roadmap influence • Win back at-risk accounts and defeat competitive threats through value-led conversations • Build the playbook for how Siena operates in strategic accounts from first-principles, not from importing what you did elsewhere

• You own the commercial relationship for Siena's highest-value brands: renewals, expansion, executive trust, and knowing your accounts better than anyone. • A deployment strategist owns product outcomes for the same accounts — together you're the Siena pod. • You hold your accounts to specific, measurable commercial outcomes: net dollar retention, expansion, and the strength of the executive relationship. • You own our Growth and Strategic segment accounts - not the full customer book - and work at the intersection of customer, sales, and your deployment strategist. • You'll lead commercial reviews, executive account mapping, and account planning, and run in-person workshops, account visits, and QBRs with your accounts. Expect moderate travel.

• Own a defined Siena product surface and become its resident expert • Learn the platform cold: how the agents behave, how they work together, prompt engineering, config, deployment • Diagnose agent behavior with authority: product, config, or customer setup • Run the feedback loop to the PM: turn the patterns you see across customers into clear, prioritized signal that shapes the roadmap • Own enablement: the docs, guides, and live-chat material that sit between too-technical and too-marketing • Run webinars and demos, support sales, and do the market research the team needs • Work the support queue on your surface, not as overflow, but as your direct line to how the product behaves

• Own the hard problems end to end • Debug the agents and the prompts • Build so it doesn't happen twice • Close the loop to Product • Raise the team's floor • Know where your scope ends

• Run demos built around the prospect's actual problems and data — across our Support, Shopping, Social, Reviews, and Voice agents and Siena Intelligence. • Lead live technical discovery and validation: map the prospect’s stack, answer “can it do X?” honestly, and propose solutions when the standard product doesn’t fit. • Maintain and refresh the demo environment and demo asset library (live demos, video assets, scenario flows) so the whole GTM team can sell accurately. • Assist with RFPs and security questionnaires • Own multi-week POC / trial programs end to end: kickoff, integration connect, journey and automation buildout, weekly working sessions, QA, troubleshooting, and final readout. • Write clean technical handoffs so Deployment can carry the customer past go-live. • Scope integrations across the e-commerce CX stack; decide native-vs-custom build and partner with Engineering on what gets built. • Build and test integrations yourself — write custom actions, test and validate in Postman against live or sandbox endpoints. • Draft, scope, and price Statements of Work for custom configuration and integration work, and translate feasibility into realistic effort and cost. • Be the connective tissue across Sales, Engineering, Product, and CS — triaging customer issues, filing well-scoped Linear tickets, and escalating to the right owner. • Act as the field-to-product feedback conduit: bring concrete product gaps and roadmap input into product reviews, grounded in real deals. • Support pricing conversations with the technical ROI and volume case (the AE owns commercial terms). • Contribute to internal enablement — training AEs and CSMs to demo, and building reusable enablement content.

• Set technical direction and architecture for major areas of the platform, and bring the rest of engineering with you. • Own our hardest problems end to end: the ambiguous, cross-cutting, high-stakes work where the right path is not obvious yet. • Make the build/buy and architectural calls that shape the platform for years, and write down the reasoning so others can build on it. • Take cutting-edge language models into production inside enterprise customer workflows, where reliability and safety actually matter. • Multiply the team. Raise the engineering bar through design review, technical mentorship, and the standard you set by example. • Identify the technical initiatives we should be running, rather than waiting to be handed them. • Keep us honest on reliability, performance, and scale as we grow across channels and brands.

• Own features and systems across the full stack, frontend, backend, and infrastructure, from problem definition through production. • Partner with product to break down ambiguous scope and ship in iterative, high-impact releases. • Make real architectural and design decisions in your area, and explain the reasoning so the team can build on it. • Take cutting-edge language models into enterprise customer workflows, where reliability and safety actually matter. • Solve hard engineering problems: API performance, microservices, scaling across channels and brands. • Maintain and improve our AWS infrastructure with a DevOps mindset. • Raise the bar around you. Share what you know, review thoughtfully, and help teammates level up.

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. As Siena evolves its pricing and billing infrastructure, you'll be part of how that gets built. 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 — ideally with a background or genuine interest in finance, RevOps, or billing operations, but what matters most is aptitude, ownership instinct, and the ability to learn fast. Qualifications - Detail-obsessed and systems-minded - Drawn to financial operations - AI-curious and resourceful - Comfortable with dense material - Strong communicator - Trustworthy and discreet Requirements - 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 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.

Role Description You are, first, a product expert. You can take a complex, fast-moving product and dissect it into something people understand - across whatever format the moment needs: a demo, a workshop, a doc, a short video, a certification path. Second, you know how to turn that understanding into something that sells. You break features into sellable units, and you teach the team how to put them in front of a customer. Third, you build the community that turns all of that into a network that compounds. It's a founding role: a blank page, a fast product, and real ownership over the result. No playbook waiting for you, and no content team underneath you—you make the thing. This isn't a fit if you've spent your career running someone else's training program inside a big org. It is a fit if you live in the product, build with AI, and have shipped something real from zero. What you'll own - Product fluency, made teachable. - Sales enablement. - Siena Academy. - Customer onboarding. - Internal team education. - Community. - AI agents that scale you. What success looks like in 90 days - You know the product cold and the team knows it because of you. - Demos are sharper and demo-to-close is measurably up. - Siena Academy v2 is live. - Onboarding from signed to first value is documented, repeatable, and measurably shorter than today. - One-to-many product workshops run weekly. Qualifications - Product-fluent, first and foremost. - A translator. - An exceptional teacher and storyteller. - AI-native. - A builder. - An operator. Nice to have - You've done this at Intercom (or Fin), Attentive, Klaviyo, Gorgias, Recharge, Shopify, Gainsight, Notion, Figma, or Linear. - You're doing this exact job at another AI company today. - You've scaled a customer community from zero. - You've built product or sales enablement that measurably moved win rate. This is not the role for you if - You're a generalist trainer who's comfortable a layer above the product. - Your background is L&D or corporate training only. - You've managed a community but never built a compounding system. - You need a content team underneath you to produce output. - You treat education as separate from revenue. 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. - AI-fluency. Make AI your second nature. - Tackle unsolved problems. 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. 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. Everyone gets premium accounts plus a quarterly budget for new tools. Equal Employment Opportunity 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.