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.

The Role: Customer Success Manager

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.

What Success Looks Like

You are accountable for:

Automation and conversion rates

Support cost efficiency

CX quality, including CSAT and NPS

Retention and expansion

What You’ll Do

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

Who you are

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 renewing and expanding enterprise customers in complex, high value accounts

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.

Bonus Points

• Experience with a native AI technology company

  E-commerce experience

  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.