Siena is the The Agent of Record for CX, built for consumer brands like Spanx, FIGS, Brooklinen, and Grüns.
It runs as a connected multi-agent stack on top of a shared intelligence layer: agents that sell, support, listen, handle social and voice across the entire customer journey, turning every conversation into signal you can act on.
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 set the bar rather than follow one, keep reading.
The Role
You own the commercial relationship for Siena's highest-value brands: renewals, expansion, executive trust, and knowing your accounts better than anyone. A deployment strategist owns product outcomes for the same accounts — together you're the Siena pod.
You hold your accounts to specific, measurable commercial outcomes: net dollar retention, expansion, and the strength of the executive relationship. You own our Growth and Strategic segment accounts - not the full customer book - and work at the intersection of customer, sales, and your deployment strategist. You'll lead commercial reviews, executive account mapping, and account planning, and run in-person workshops, account visits, and QBRs with your accounts. Expect moderate travel.
What Success Looks Like
You are accountable for:
Net dollar retention (NDR) of your book
Expansion quota attainment
Executive relationship health across your accounts
What You'll Do
Own the Commercial Relationship End to End
Own a portfolio of Growth and Strategic accounts from post-onboarding through long-term growth
Build a concrete account plan with each customer: the commercial, operational, and CX metrics you're moving, and the timeline for moving them
Monitor account health, and when performance slips, bring in the deployment strategist — you own the customer communication and accountability while they execute the fix
Hold customers and internal teams accountable when progress stalls
Track and communicate impact clearly using data, not anecdotes
Map the Account and Build Executive Trust
Maintain a living stakeholder map for every account: who champions Siena, who's skeptical, who signs, and what changes when their org changes. Act on org changes before they become renewal risk.
Build durable relationships with executive decision-makers, not only day-to-day contacts. Own the executive cadence for your book so leadership sees Siena's value before the renewal conversation starts.
Drive Commercial Outcomes
Own renewal negotiations and independently identify and close expansion opportunities, including navigating procurement, pricing, and contract tradeoffs
Understand the cost, headcount, and revenue implications of CX decisions
Engage confidently with senior stakeholders, including CX leaders and executives
Quantify and communicate customer ROI using metrics tied to cost savings, efficiency, or revenue impact
Bring Product Depth to the Relationship
Develop a strong understanding of Siena's product: how the core agents work together, the customer problems they solve, and how to position them in customer conversations
Confidently explain product capabilities, connect them to business outcomes, and guide customers on the best strategic use cases
Lead Cross-Functional Execution
Turn vague customer problems into clear problem statements and execution plans, partnering with other teams when needed
Participate in cross-functional projects and build strong internal partnerships
Who You Are
Experience & Background
Startup background essential - fast-paced, ambiguous environments, comfortable wearing many hats
3+ years in account management, CSM, or a client-facing commercial role with technical, complex software solutions
E-commerce or CX industry experience strongly preferred - customers respond better to AMs who speak their language
Demonstrated success independently renewing and expanding enterprise customers in complex, high-value accounts - owning the commercial conversation, not just supporting it. Minimum bar: negotiated at least one $100k+ deal
Enterprise experience: managed complex orgs, sold to multiple stakeholders
Experience working closely with product and engineering teams
Experience analyzing usage patterns and competitive landscapes, and translating data into actionable account strategies
Comfort operating in fast-moving, evolving environments
Mindset & Approach
Self-directed: 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
Proactive, and pushes when needed
Balances empathy with commercial impact - willing to challenge the status quo when it blocks results
Curious by nature - actively learns new domains, products, or systems without being told
Everyone at Siena Is Technical
This bar applies to every role at Siena, including this one.
Hands-on prompt engineering experience - able 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
Comfort with a rapidly evolving AI landscape - stays current on AI capabilities and applies them to your work
Bonus Points
Experience with a native AI technology company
Comfort with API integrations, conversation flow design, and business intelligence tools
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.
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 [email protected].
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.
