AI Strategist

AI Strategist at Siena AISiena is the first intelligence layer for customer experience—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.We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels. Siena powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human.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 automation for automation's sake.Deliver a wide range of services across the customer lifecycle: partnership on strategic planning, leading hands-on workshops, conducting automation audits, delivering training programs (virtual and in-person), and ensuring ongoing automations perform as promised.What You'll DoPartner with CX leaders on AI-first strategyWork with VPs of CX, Directors of Customer Support, and Operations Leaders to design their AI transformation roadmap.Diagnose blockers (technical limitations, operational gaps, stakeholder alignment) and design solutions.Challenge assumptions about existing processes—help leaders reimagine workflows for an AI-first world.Balance quick wins with strategic long-term initiatives that transform how teams operate.Own relationships with key accounts where ongoing strategic partnership drives the most value.Triage technical issues and hold support and engineering teams accountable for resolution.Deliver high-impact services across the customer journeyLead Automation Workshops, collaboratively designing and building automations with customer teams.Deliver engaging AI Manager Training sessions (virtual and in-person) that build customer confidence and product fluency.Conduct automation audits on live environments to identify optimization opportunities and expansion potential.Perform systematic QA on automations, reviewing conversation data to verify performance and identify improvements.Jump into accounts you don't know well to solve specific focus areas—a new channel launch, a stalled automation program, or a critical optimization need.Drive strategic outcomes through CX expertiseIdentify high-value automation opportunities based on deep understanding of CX operations and business impact.Prioritize by business impact, understand customer goals, diagnose blockers, and think several steps ahead.Own measurable outcomes (CSAT improvement, cost reduction, automation rate growth) not just task completion.Proactively spot issues before customers do, identify expansion opportunities, and keep accounts healthy.Balance being consultative and strategic with hands-on and tactical depending on customer needs.Enable customer self-sufficiency and continuous improvementTeach customers to think in AI-first terms and build their own capabilities.Create "aha moments" where CX leaders and teams see possibilities they didn't know existed.Provide actionable feedback reports with recommended optimizations based on QA insights and strategic analysis.Build customer confidence and capability, not dependency.Collaborate Across Functions To Amplify ImpactWork with Professional Services team members and broader CX organization to communicate customer needs and blockers.Translate customer insights and patterns into actionable feedback for Product and Engineering.Communicate technical concepts to non-technical stakeholders and vice-versa.Help scale services by identifying repeatable frameworks or product features.Share knowledge and help teammates grow strategic and technical capabilities.Own Your Work and Drive ResultsBalance responsiveness to urgent requests with proactive strategic work.Navigate ambiguity and make judgment calls about priorities and trade-offs.Engage in difficult conversations—push back on low-impact requests and challenge broken processes.Take ownership of customer outcomes, not just tasks.Who You AreCX Operations Expert with Strategic Judgment5+ years in customer experience operations, preferably in e-commerce or omnichannel support.Deep understanding of CX workflows, pain points, metrics, tools, and what makes teams successful.Experience with enterprise CX platforms (Zendesk, Gorgias, Kustomer, or similar).Diagnose whether problems are technical, operational, or stakeholder-related and prioritize accordingly.Comfortable advising CX leaders on organizational design, process optimization, and transformation strategy.Versatile Professional Delivering Across Multiple Service TypesLead training sessions, run workshops, conduct audits, perform QA, and consult on strategy.Switch between tactical work and strategic thinking based on customer needs.Systematic thinker who can design repeatable service delivery processes.Comfortable with high-volume work (10-15 customer sessions per week) while maintaining quality.Able to own long-term customer relationships and build trust at multiple levels.Engaging Facilitator and TeacherLead compelling live sessions (training, workshops, audit presentations, strategy sessions) that keep people engaged.Present virtually and in-person to groups ranging from practitioners to executive stakeholders.Make scripted content personalized and adapt on the fly.Balance empathy and support with directness about needed change.Build customer confidence and capability.AI-Fluent and Technically CapableExcited about AI's potential to transform customer experience.Comfortable with automation logic, conversation flows, prompt design, and agent behavior.Understand how technical systems work to collaborate with engineers without writing production code.Experience with low-code automation tools, AI platforms, or similar technologies.Translate business needs into technical requirements.Proactive and Outcome-FocusedBias toward action—solve problems and keep things moving.Anticipate customer needs, identify risks early, spot expansion opportunities.Focus on business impact and measurable results.Comfortable having difficult conversations and challenging customers.Take ownership without waiting to be asked.Collaborative and AdaptableWork effectively across functions (CSMs, Engineers, Product, PS team).Give and receive direct feedback well.Comfortable with fast pace, changing priorities, and some ambiguity.Open to travel for in-person customer workshops and training sessions.Help teammates grow and share knowledge.Nice to HavePrevious experience at high-growth SaaS companies serving mid-market or enterprise clients.Hands-on experience with Siena or similar conversational AI platforms.Background in professional services, consulting, or advisory roles.Experience training or enabling partner/BPO networks.Understanding of e-commerce platforms and integrations.Experience conducting business audits or assessments.Track record of working effectively with product and engineering teams.Comfort presenting to and advising senior executives.What You'll GetFront-row seat to the future of customer experience and AI.Variety in work—strategic consulting one day, hands-on workshops the next.Direct impact on customer success and our service delivery model.Learning budget to fuel your growth.Premium AI tools (ChatGPT, Claude, Perplexity Pro, Cursor) plus quarterly budget for new tools.Opportunity for travel to customer sites for in-person training and workshops.Clear growth pathways: specialize deeper in strategy/CX consulting or grow into team leadership.Why 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 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 in the next decades.Our ValuesWe thrive on curiosity, customer-obsession, and ownership without being asked. We fix problems first, explain later, and give and receive direct feedback. High standards move at startup speed, and we build real relationships.Our Approach to AIWe treat AI like a natural extension of ourselves—building our own ecosystem of agents for research, debugging, writing, analysis, or coding. Everyone gets premium AI accounts and a quarterly budget for new tools. We share knowledge through demo days, Slack threads, and learning from each other.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.J-18808-Ljbffr