AI Strategist

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 RoleAs an AI Strategist, you're the connective tissue between traditional CX operations and AI-first transformation. You work with senior customer stakeholders to build strategies that integrate AI in ways that drive real, measurable results - not just automate for automation's sake.You'll deliver a wide range of services across the customer lifecycle: partnering with senior customer stakeholders on strategic planning, leading hands-on workshops, conducting automation audits, delivering training programs (both virtual and in-person), and ensuring ongoing automations perform as promised. You're equally comfortable owning long-term customer relationships and jumping into new accounts to solve specific high-priority challenges.This role is part of our Professional Services team. You understand how great CX organizations operate, and you help them evolve those operations for an AI-native world. You consult on strategy while rolling up your sleeves to execute - designing roadmaps one day, teaching teams to build automations the next, conducting audits to unlock the next phase of value throughout.You're the bridge between what Siena's platform can do and what customers need it to do. Your deep CX expertise helps you spot opportunities others miss, and your ability to execute across multiple service offerings makes you invaluable to both customers and our internal teams.What You’ll Do:Partner with CX leaders on AI-first strategyWork with VPs of CX, Directors of Customer Support, and Operations Leaders to design their AI transformation roadmapDiagnose what's blocking progress (technical limitations, operational gaps, stakeholder alignment) and design solutionsChallenge assumptions about existing processes—help leaders reimagine workflows for an AI-first world, not just automate broken onesBalance quick wins with strategic long-term initiatives that fundamentally transform how their teams operateOwn relationships with key accounts where ongoing strategic partnership drives the most valueTriage technical issues and keep support and engineering teams accountable for resolutionDeliver high-impact services across the customer journeyLead Automation Workshops where you collaboratively design and build automations with customer teamsDeliver engaging AI Manager Training sessions (virtual and in-person) that build customer confidence and product fluencyConduct automation audits on live customer environments to identify optimization opportunities and expansion potentialPerform systematic QA on automations, reviewing conversation data to verify performance and identify improvementsJump into accounts you don't know well to solve specific focus areas—a new channel launch, a stalled automation program, a critical optimization needDrive strategic outcomes through CX expertiseIdentify high-value automation opportunities based on deep understanding of CX operations and business impactThink several steps ahead: understand customer goals, diagnose blockers, prioritize by business impactOwn measurable outcomes (CSAT improvement, cost reduction, automation rate growth) not just task completionBe proactive: spot issues before customers do, identify expansion opportunities, keep accounts healthyBalance being consultative and strategic with being hands-on and tactical depending on what the customer needsEnable customer self-sufficiency and continuous improvementTeach customers to think in AI-first terms and build capabilities themselves rather than depending on usCreate "aha moments" where CX leaders and their teams see possibilities they didn't know existedProvide actionable feedback reports with recommended optimizations based on QA insights and strategic analysisBuild customer confidence and capability, not dependencyCollaborate Across Functions To Amplify ImpactWork with other Professional Services team members and the broader CX organization to understand and communicate the big picture of customer needs and blockersTranslate customer insights and patterns into clear, actionable feedback that helps Product and Engineering teams improve SienaCommunicate technical concepts to non-technical stakeholders and business context to technical teamsHelp scale our service offerings by identifying patterns that should become repeatable frameworks or product featuresShare knowledge and help teammates grow their strategic and technical capabilitiesOwn your work and drive resultsBalance being responsive to urgent requests with proactive strategic workNavigate ambiguity and make judgment calls about priorities and tradeoffsHave difficult conversations when needed—push back on low-impact requests, challenge broken processesTake ownership of customer outcomes, not just your individual tasksWho You areCX operations expert with strategic judgment5+ years in customer experience operations, preferably in e-commerce or omnichannel supportDeep understanding of CX workflows, pain points, metrics, tools, and what makes teams successfulExperience with enterprise CX platforms (Zendesk, Gorgias, Kustomer, or similar)You've lived the problems customers are trying to solve—you know what "good" looks likeYou can diagnose whether problems are technical, operational, or stakeholder-related and prioritize accordinglyComfortable advising CX leaders on organizational design, process optimization, and transformation strategyVersatile Professional Delivering Across multiple service typesComfortable leading training sessions, running workshops, conducting audits, performing QA work, and consulting on strategyCan switch between hands-on tactical work and strategic thinking depending on what the customer needsSystematic thinker who can design processes for repeatable service deliveryComfortable with high-volume work (10-15 customer sessions per week) while maintaining qualityAble to own long-term customer relationships and build trust at multiple levels of the organizationEngaging facilitator and teacherCan lead compelling live sessions (training, workshops, audit presentations, strategy sessions) that keep people engagedComfortable presenting virtually and in-person to groups ranging from practitioners to executive stakeholdersAbility to make scripted content feel personalized and adapt on the fly to customer questionsBalance being empathetic and supportive with being direct about what needs to changeBuild customer confidence and capability, not dependencyAI-fluent and technically capableExcited about AI's potential to transform customer experienceComfortable with automation logic, conversation flows, prompt design, and agent behaviorDon't need to write production code, but understand how technical systems work well enough to collaborate with engineersExperience with low-code automation tools, AI platforms, or similar technologiesCan translate between business needs and technical requirementsProactive and outcome-focusedBias toward action - you solve problems and keep things movingThink ahead: anticipate customer needs, identify risks early, spot expansion opportunitiesFocus on business impact and measurable results, not just completing tasksComfortable having difficult conversations and challenging customers when neededTake ownership without waiting to be askedCollaborative and adaptableWork effectively across functions (CSMs, Engineers, Product, other PS team members)Give and receive direct feedback wellComfortable with fast pace, changing priorities, and some ambiguityOpen to travel for in-person customer workshops and training sessionsShare knowledge and help teammates growWhat Success Looks LikeStrategic consulting impactCX leaders view you as a trusted advisor who helps them think bigger about AI transformationYour strategic roadmaps balance quick wins with long-term transformation initiativesYou challenge customers constructively and help them reimagine their operationsCustomers execute on your recommendations because they're grounded in their reality and business goalsService delivery excellenceCustomers consistently leave your sessions with actionable plans and improved capabilitiesTraining and workshops (virtual and in-person) result in measurable improvements in product adoptionAudit findings lead to clear roadmaps that drive real business outcomesQA cycles identify high-impact optimizations that improve automation performanceRelationship ownership and flexibilityYou build deep, trusted relationships with key accounts that drive ongoing valueYou can also jump into new accounts and quickly add value on specific initiativesCSMs and other team members trust your judgment and actively seek your inputYou balance being strategic and consultative with being hands-on and executionalCollaboration and influenceYour customer insights help Product and Engineering teams prioritize the right improvementsYou translate patterns across customers into clear, actionable feedbackProfessional Services and CX teams value your perspective and incorporate your inputYou help other team members grow their strategic thinking and customer skillsNice to HavePrevious experience at high-growth SaaS companies serving mid-market or enterprise clientsHands-on experience with Siena or similar conversational AI platformsBackground in professional services, consulting, or advisory rolesExperience training or enabling partner/BPO networksUnderstanding of e-commerce platforms and integrationsExperience conducting business audits or assessmentsTrack record of working effectively with product and engineering teamsComfort presenting to and advising senior executivesWhat You'll GetFront-row seat to the future of customer experience and AIVariety in your work—strategic consulting one day, hands-on workshops the next, audits and training throughoutDirect impact on customer success and our service delivery modelLearning budget to fuel your growthPremium AI tools (ChatGPT, Claude, Perplexity Pro, Cursor) plus quarterly budget for new toolsOpportunity for travel to customer sites for in-person training and workshopsClear growth pathways: specialize deeper in strategy/CX consulting or grow into team leadershipWhy 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.