Customer Success Manager

Meet Siena

Siena is the Agent of Record for consumer brands. One agent that owns the entire customer journey, running on a shared intelligence layer no point tool can replicate.

Consumer brands run ten or more disconnected tools to manage their customers. We collapse that stack into a single agent. It started with support, the hardest surface a brand has, and it expands from there: Shopping Agent, Social Agent, Siena working alongside a brand's own operators. One agent across every surface, with shared memory, shared context, and shared tools.

Hundreds of brands already run real customer volume on Siena in production. This is built, working, and growing, and we are racing to build what comes next.

The team

We are a small, fully distributed, global team. We have built leverage into how we work, which is what lets a team this size move at the speed we do.

We hire athletes. Everyone here owns real outcomes, defaults to writing over meetings, communicates with directness, and acts the moment they see something worth acting on. Low ego, high standards, fast clock.

If you want to own real problems rather than close tickets, keep reading.

The Role

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 own our Growth and Strategic segment accounts - not the full customer book. 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 resolution rates

• Support cost efficiency

• CX quality, including CSAT and NPS

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

What You'll Do

Own Customer Outcomes End to End

• Own a portfolio of Growth and Strategic 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:

• Startup background essential - fast-paced, ambiguous environments, comfortable wearing many hats

• 3+ years in Customer Success Management, account management, or client-facing strategic roles with more technical and complex software solutions

• E-commerce or CX industry experience strongly preferred - customers respond better to CSMs who speak their language

• Demonstrated success independently renewing and expanding enterprise customers in complex, high-value accounts - including owning the commercial conversation, not just supporting it. Minimum bar: negotiated at least one $100k+ deal

• Enterprise experience required: managed complex orgs, sold to multiple stakeholders

• 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. Must go deeper than transcription tools or using ChatGPT for emails — has built an agent, automated a workflow, or created a tool

• 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

Why Siena?

• Real ownership. You will own problems, not tasks, with the autonomy to solve them your way and the trust to do it without a manager in your inbox.

• Work that ships and matters. What you build reaches real consumer brands fast.

• A category we are creating. The Agent of Record is new ground, with unsolved problems and cutting-edge models, not a crowded field to compete in.

• A team that respects your judgment. Globally distributed, async-first, low bureaucracy. We hire adults and treat you like one.

• Great salary plus equity or stock grants. Own a piece of what you build.

• Learning budget. If you are growing, so are we.

• AI-fluency by default. Few places will push your work with production AI further or faster.

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.

We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at talent@siena.cx.

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.