Scaled Customer Success Manager

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, and explore new opportunities

• Anticipate customer challenges and provide proactive solutions based on deep understanding

• Partner with cross-functional teams to reduce CSM workload and improve customer experience

Experience & Background:

• 3+ years in Customer Success Management, ideally with some experience in digital CS, customer marketing, or scaled programs 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

• Familiarity with customer success platforms (Vitally, ChurnZero, Catalyst), CRM systems (HubSpot, Salesforce) and other scaled CS technologies.

• Strong writer and communicator: You can explain complex AI concepts clearly and create content that drives action

• 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.