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 (10-15 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.
