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 Scaled 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.

This role isn't just about managing accounts; it's about building scalable systems, creating educational content, and reimagining how we serve customers at scale.

You'll be joining at a pivotal moment as we transition from a purely account-based model to a hybrid approach that combines high-touch relationship management with scalable digital engagement. This role is part CSM, part content creator, part strategist - perfect for someone who wants to shape the future of customer success.

What You'll Do

Strategic Growth & Optimization:

• Own the complete growth and optimization journey for our SMB customers in a pooled model approach - from onboarding through expansion.

• Configure complex automations and provide best practice recommendations during live strategy sessions

• Intervene proactively when health scores drop or risk signals appear

• Host regular office hours and group sessions

• Design the Commercial customer journey and continuously optimize it

• Build measurement frameworks to understand what's working

• 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

• 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 & Content Creation

• Create educational content that serves customers across all segments: video tutorials, knowledge base articles, best practice guides, workflow templates

• Design and execute campaigns: feature adoption pushes, upsell opportunities, seasonal readiness, product update communications

• Build community initiatives: Engage actively in our private Slack community as a thought leader and trusted resource and help run user groups

• Develop scalable engagement strategies: automated email sequences, milestone-based touchpoints, self-serve resources

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. Influence GTM strategy.

• Investigate root causes, challenge assumptions