Customer Success Manager

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.

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.

This is not a relationship-only CSM role. As a CSM at Siena, you own a portfolio of customers and hold them to specific, measurable outcomes. You are accountable for how well Siena performs and how much value customers actually realize.

You will operate at the intersection of customer, product, sales, and engineering. You’ll lead audits, improvement plans, and cross-functional execution to move real metrics, not just run QBRs.

You are accountable for:

• Automation and conversion rates

• Support cost efficiency

• CX quality, including CSAT and NPS

• Retention and expansion — including owning renewal negotiations and independently identifying and closing expansion opportunities

Own Customer Outcomes End to End

• Own a portfolio of accounts from post-onboarding through long-term success

• Translate customer goals into concrete success plans tied to operational and CX metrics

• Diagnose performance issues and lead improvement plans with clear owners and timelines

• Hold customers and internal teams accountable when progress stalls

• Track and communicate impact clearly using data, not anecdotes

Technical Excellence & Product Mastery

• Master all product features, common use cases, and understand our integration capabilities

• Explain technical concepts clearly to non-technical stakeholders

• Understand complex automations and provide best practice recommendations

• Consistently demonstrate new features to clients and tailor product updates based on specific needs

Bring Commercial and Business Acumen

• Understand the cost, headcount, and revenue implications of CX decisions

• Engage confidently with senior stakeholders including CX leaders and executives

• Identify expansion opportunities rooted in demonstrated value

• Quantify and communicate customer ROI using metrics tied to cost savings, efficiency, or revenue impact

• Navigate procurement, pricing conversations, and contract tradeoffs with confidence

Lead Cross-Functional Execution

• Turn vague customer problems into clear problem statements and execution plans. May include partnering with other teams including sales, services or product to achieve client outcomes

• Bring structured, well-scoped customer feedback back to the product and engineering teams

• Participate in cross-functional projects and develop strong internal partnerships

• Mentor team members and influence others' professional growth

Customer Education & Enablement

• Lead training sessions with key stakeholders

• Create customer-facing content, training materials, and improve existing documentation

• Design and facilitate strategy sessions, workshops, updates, and webinars showcasing advanced use cases

• Engage actively in our private Slack community as a thought leader and trusted resource

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

• Demonstrated success independently renewing and expanding enterprise customers in complex, high-value accounts — including owning the commercial conversation, not just supporting it

• Experience working closely with product and engineering teams

• Comfort operating in fast-moving, evolving environments

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

• Comfort with rapidly evolving AI landscape by staying current on AI capabilities and applying them to customer success.

Mindset & Approach:

• You are a self-directed professional who asks for help when needed and brings solutions rather than just raising issues

• You thrive in fast-paced startup environments with evolving priorities and ambiguous challenges

• You are proactive and push when needed.

• You balance empathy with business impact and are willing to challenge the status quo when it blocks results.

• You are curious by nature. You actively learn new domains, products, or systems without being told.

• Experience with a native AI technology company

• E-commerce experience

• 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.

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.

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.