Customer Success Manager

Meet SienaSiena 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 teamWe'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.🎯 The Role: Customer Success ManagerThis is not a relationship-only CSM role. As a CSM at Siena, you own a portfolio of customers and hold them to specific, measurable outcomes. You are accountable for how well Siena performs and how much value customers actually realize.You will operate at the intersection of customer, product, sales, and engineering. You’ll lead audits, improvement plans, and cross-functional execution to move real metrics, not just run QBRs.What Success Looks LikeYou are accountable for:Automation and conversion ratesSupport cost efficiencyCX quality, including CSAT and NPSRetention and expansion — including owning renewal negotiations and independently identifying and closing expansion opportunitiesWhat You’ll DoOwn Customer Outcomes End to EndOwn a portfolio of accounts from post-onboarding through long-term successTranslate customer goals into concrete success plans tied to operational and CX metricsDiagnose performance issues and lead improvement plans with clear owners and timelinesHold customers and internal teams accountable when progress stallsTrack and communicate impact clearly using data, not anecdotesTechnical Excellence & Product MasteryMaster all product features, common use cases, and understand our integration capabilitiesExplain technical concepts clearly to non-technical stakeholdersUnderstand complex automations and provide best practice recommendationsConsistently demonstrate new features to clients and tailor product updates based on specific needsBring Commercial and Business AcumenUnderstand the cost, headcount, and revenue implications of CX decisionsEngage confidently with senior stakeholders including CX leaders and executivesIdentify expansion opportunities rooted in demonstrated valueQuantify and communicate customer ROI using metrics tied to cost savings, efficiency, or revenue impactNavigate procurement, pricing conversations, and contract tradeoffs with confidenceLead Cross-Functional ExecutionTurn vague customer problems into clear problem statements and execution plans. May include partnering with other teams including sales, services or product to achieve client outcomesBring structured, well-scoped customer feedback back to the product and engineering teamsParticipate in cross-functional projects and develop strong internal partnershipsMentor team members and influence others' professional growthCustomer Education & EnablementLead training sessions with key stakeholdersCreate customer-facing content, training materials, and improve existing documentationDesign and facilitate strategy sessions, workshops, updates, and webinars showcasing advanced use casesEngage actively in our private Slack community as a thought leader and trusted resourceWho you areExperience & Background:3+ years in Customer Success Management, account management, or client-facing strategic roles with more technical and complex software solutions. Proven track record with customer service technology platforms or e-commerce ecosystemsDemonstrated success independently renewing and expanding enterprise customers in complex, high-value accounts — including owning the commercial conversation, not just supporting itExperience working closely with product and engineering teamsComfort operating in fast-moving, evolving environmentsTechnical & Analytical Competencies:Experience in AI/ML space, particularly conversational AI or automation platformsHands-on prompt engineering experience with ability to optimize AI responses, train conversation flows, and refine model outputsExperience analyzing usage patterns, competitive landscapes, and translating data into actionable strategiesComfort with API integrations, conversation flow design, and business intelligence toolsComfort with rapidly evolving AI landscape by staying current on AI capabilities and applying them to customer success. Mindset & Approach:You are a self-directed professional who asks for help when needed and brings solutions rather than just raising issuesYou thrive in fast-paced startup environments with evolving priorities and ambiguous challengesYou are proactive and push when needed. You balance empathy with business impact and are willing to challenge the status quo when it blocks results. You are curious by nature. You actively learn new domains, products, or systems without being told. Bonus PointsExperience with a native AI technology companyE-commerce experienceWhy 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 valuesThe 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 AIThe 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.