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
We'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 Do
Strategic Growth & Optimization:
Own the complete growth and optimization journey for existing customers, fresh from onboarding through expansion
Configure complex automations and provide best practice recommendations during live strategy sessions
Analyze usage patterns and trends to identify actionable insights that drive business impact
Leverage client data and industry benchmarks to challenge assumptions and demonstrate value
Document client outcomes and translate them into clear success plans with tracked priorities
Proactively identify obstacles, issues, and expansion opportunities while maintaining focus on company objectives
Technical Excellence & Product Mastery:
Master all product features, common use cases, and integration capabilities
Perform advanced troubleshooting and resolve complex technical challenges
Consistently demonstrate new features to clients and tailor product updates based on specific needs
Understand complex business processes and competitive landscape dynamics
Customer Education & Enablement:
Lead strategic discussions and training sessions with key stakeholders
Create customer-facing content, training materials, and improve existing documentation
Design and facilitate strategy sessions, workshops, and webinars showcasing advanced use cases
Engage actively in our private Slack community as a thought leader and trusted resource
Relationship Management & Communication:
Develop strong stakeholder relationships and manage escalations effectively
Consistently engage key decision-makers to drive strategic initiatives
Present insights and recommendations confidently to C-level executives
Maintain calmness during crises and adapt communication style to different audiences
Process Development & Cross-Functional Leadership:
Build foundational processes and playbooks that scale the Customer Success function
Participate in cross-functional projects and develop strong internal partnerships
Implement best practices and drive efficiency improvements across customer operations
Mentor team members and influence others' professional growth
Voice of Customer & Strategic Insight:
Serve as primary conduit between customers and product team, capturing feedback and pain points
Investigate root causes, challenge assumptions, and explore new opportunities
Anticipate customer challenges and provide proactive solutions based on deep understanding
Experience & 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 ecosystems
Strong technical aptitude with ability to configure complex automations and troubleshoot AI workflows
Demonstrated ability to drive customer growth, retention, and expansion through data-driven insights
Technical & Analytical Competencies:
Experience in AI/ML space, particularly conversational AI or automation platforms
Hands-on prompt engineering experience with ability to optimize AI responses, train conversation flows, and refine model outputs
Experience analyzing usage patterns, competitive landscapes, and translating data into actionable strategies
Comfort with API integrations, conversation flow design, and business intelligence tools
Mindset & Approach:
Self-directed professional who asks for help when needed and brings solutions rather than just raising issues
Thrives in fast-paced startup environments with evolving priorities and ambiguous challenges
Strong self-awareness of personal strengths and weaknesses with commitment to continuous learning
Highly Valued Qualifications
Background training, mentoring, or scaling customer success teams in high-growth environments
Deep expertise in e-commerce operations, customer journey optimization, or omnichannel support
Previous experience at high-growth SaaS companies serving enterprise or mid-market clients
Track record of participating in cross-functional projects and driving team success initiatives
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.
