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COO scaling global DTC natural-health brand through operations and P&L ownership

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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.About The RoleWe're seeking a Customer Success Manager who will serve as a trusted advisor to our clients, driving continuous growth in platform adoption and optimization. You'll proactively identify expansion opportunities, guide customers through advanced use cases, and ensure they're maximizing ROI from Siena's AI-powered customer service solutions.What You'll DoStrategic Growth & Optimization:Own the complete growth and optimization journey for existing customers, fresh from onboarding through expansionConfigure complex automations and provide best practice recommendations during live strategy sessionsAnalyze usage patterns and trends to identify actionable insights that drive business impactLeverage client data and industry benchmarks to challenge assumptions and demonstrate valueDocument client outcomes and translate them into clear success plans with tracked prioritiesProactively identify obstacles, issues, and expansion opportunities while maintaining focus on company objectivesTechnical Excellence & Product Mastery:Master all product features, common use cases, and integration capabilitiesPerform advanced troubleshooting and resolve complex technical challengesConsistently demonstrate new features to clients and tailor product updates based on specific needsUnderstand complex business processes and competitive landscape dynamicsCustomer Education & Enablement:Lead strategic discussions and training sessions with key stakeholdersCreate customer-facing content, training materials, and improve existing documentationDesign and facilitate strategy sessions, workshops, and webinars showcasing advanced use casesEngage actively in our private Slack community as a thought leader and trusted resourceRelationship Management & Communication:Develop strong stakeholder relationships and manage escalations effectivelyConsistently engage key decision-makers to drive strategic initiativesPresent insights and recommendations confidently to C-level executivesMaintain calmness during crises and adapt communication style to different audiencesProcess Development & Cross-Functional Leadership:Build foundational processes and playbooks that scale the Customer Success functionParticipate in cross-functional projects and develop strong internal partnershipsImplement best practices and drive efficiency improvements across customer operationsMentor team members and influence others' professional growthVoice of Customer & Strategic Insight:Serve as primary conduit between customers and product team, capturing feedback and pain pointsInvestigate root causes, challenge assumptions, and explore new opportunitiesAnticipate customer challenges and provide proactive solutions based on deep understandingExperience & 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 ecosystemsStrong technical aptitude with ability to configure complex automations and troubleshoot AI workflowsDemonstrated ability to drive customer growth, retention, and expansion through data-driven insightsTechnical & 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 toolsMindset & Approach:Self-directed professional who asks for help when needed and brings solutions rather than just raising issuesThrives in fast-paced startup environments with evolving priorities and ambiguous challengesStrong self-awareness of personal strengths and weaknesses with commitment to continuous learningHighly Valued QualificationsBackground training, mentoring, or scaling customer success teams in high-growth environmentsDeep expertise in e-commerce operations, customer journey optimization, or omnichannel supportPrevious experience at high-growth SaaS companies serving enterprise or mid-market clientsTrack record of participating in cross-functional projects and driving team success initiativesWhy 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.

COO to scale Happy Mammoth, a global DTC natural-health eCommerce brand.

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