AI Strategist

Meet Siena

Siena 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 team

We'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 Role

As 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 strategy

• Work with VPs of CX, Directors of Customer Support, and Operations Leaders to design their AI transformation roadmap

• Diagnose what's blocking progress (technical limitations, operational gaps, stakeholder alignment) and design solutions

• Challenge assumptions about existing processes—help leaders reimagine workflows for an AI-first world, not just automate broken ones

• Balance quick wins with strategic long-term initiatives that fundamentally transform how their teams operate

• Own relationships with key accounts where ongoing strategic partnership drives the most value

• Triage technical issues and keep support and engineering teams accountable for resolution

Deliver high-impact services across the customer journey

• Lead Automation Workshops where you collaboratively design and build 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 customer 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, a critical optimization need

Drive strategic outcomes through CX expertise

• Identify high-value automation opportunities based on deep understanding of CX operations and business impact

• Think several steps ahead: understand customer goals, diagnose blockers, prioritize by business impact

• Own measurable outcomes (CSAT improvement, cost reduction, automation rate growth) not just task completion

• Be proactive: spot issues before customers do, identify expansion opportunities, keep accounts healthy

• Balance being consultative and strategic with being hands-on and tactical depending on what the customer needs

Enable customer self-sufficiency and continuous improvement

• Teach customers to think in AI-first terms and build capabilities themselves rather than depending on us

• Create "aha moments" where CX leaders and their 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 impact

• Work with other Professional Services team members and the broader CX organization to understand and communicate the big picture of customer needs and blockers

• Translate customer insights and patterns into clear, actionable feedback that helps Product and Engineering teams improve Siena

• Communicate technical concepts to non-technical stakeholders and business context to technical teams

• Help scale our service offerings by identifying patterns that should become repeatable frameworks or product features

• Share knowledge and help teammates grow their strategic and technical capabilities

Own your work and drive results

• Balance being responsive to urgent requests with proactive strategic work

• Navigate ambiguity and make judgment calls about priorities and tradeoffs

• Have difficult conversations when needed—push back on low-impact requests, challenge broken processes

• Take ownership of customer outcomes, not just your individual tasks

Who You are CX operations expert with strategic judgment

• 5+ 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)

• You've lived the problems customers are trying to solve—you know what "good" looks like

• You can 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 types

• Comfortable leading training sessions, running workshops, conducting audits, performing QA work, and consulting on strategy

• Can switch between hands-on tactical work and strategic thinking depending on what the customer needs

• Systematic thinker who can design processes for repeatable service delivery

• Comfortable with high-volume work customer sessions per week) while maintaining quality

• Able to own long-term customer relationships and build trust at multiple levels of the organization

Engaging facilitator and teacher

• Can lead compelling live sessions (training, workshops, audit presentations, strategy sessions) that keep people engaged

• Comfortable presenting virtually and in-person to groups ranging from practitioners to executive stakeholders

• Ability to make scripted content feel personalized and adapt on the fly to customer questions

• Balance being empathetic and supportive with being direct about what needs to change

• Build customer confidence and capability, not dependency

AI-fluent and technically capable

• Excited about AI's potential to transform customer experience

• Comfortable with automation logic, conversation flows, prompt design, and agent behavior

• Don't need to write production code, but understand how technical systems work well enough to collaborate with engineers

• Experience with low-code automation tools, AI platforms, or similar technologies

• Can translate between business needs and technical requirements

Proactive and outcome-focused

• Bias toward action - you solve problems and keep things moving

• Think ahead: anticipate customer needs, identify risks early, spot expansion opportunities

• Focus on business impact and measurable results, not just completing tasks

• Comfortable having difficult conversations and challenging customers when needed

• Take ownership without waiting to be asked

Collaborative and adaptable

• Work effectively across functions (CSMs, Engineers, Product, other PS team members)

• 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

• Share knowledge and help teammates grow

What Success Looks Like Strategic consulting impact

• CX leaders view you as a trusted advisor who helps them think bigger about AI transformation

• Your strategic roadmaps balance quick wins with long-term transformation initiatives

• You challenge customers constructively and help them reimagine their operations

• Customers execute on your recommendations because they're grounded in their reality and business goals

Service delivery excellence

• Customers consistently leave your sessions with actionable plans and improved capabilities

• Training and workshops (virtual and in-person) result in measurable improvements in product adoption

• Audit findings lead to clear roadmaps that drive real business outcomes

• QA cycles identify high-impact optimizations that improve automation performance

Relationship ownership and flexibility

• You build deep, trusted relationships with key accounts that drive ongoing value

• You can also jump into new accounts and quickly add value on specific initiatives

• CSMs and other team members trust your judgment and actively seek your input

• You balance being strategic and consultative with being hands-on and executional

Collaboration and influence

• Your customer insights help Product and Engineering teams prioritize the right improvements

• You translate patterns across customers into clear, actionable feedback

• Professional Services and CX teams value your perspective and incorporate your input

• You help other team members grow their strategic thinking and customer skills

Nice to Have

• Previous 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 Get

• Front-row seat to the future of customer experience and AI

• Variety in your work—strategic consulting one day, hands-on workshops the next, audits and training throughout

• 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. 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 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.

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 AI

The 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.

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