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About the Role

You will own the commercial relationship for Siena's highest-value brands, focusing on renewals, expansion, executive trust, and deep account knowledge. You will collaborate with a deployment strategist to ensure product outcomes and drive specific, measurable commercial results like net dollar retention and expansion.

Responsibilities

• Own the commercial relationship end to end for a portfolio of Growth and Strategic accounts.
• Build concrete account plans with each customer, outlining commercial, operational, and CX metrics and timelines.
• Monitor account health and coordinate with the deployment strategist when performance issues arise, owning customer communication.
• Hold customers and internal teams accountable for progress.
• Track and communicate impact using data.
• Maintain a living stakeholder map for every account and proactively address organizational changes.
• Build durable relationships with executive decision-makers and own the executive cadence.
• Own renewal negotiations and identify/close expansion opportunities.
• 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.
• Develop a strong understanding of Siena's product capabilities and strategic use cases.
• Lead cross-functional execution by turning customer problems into actionable plans.
• Participate in cross-functional projects and build internal partnerships.

Requirements

• Startup background essential, comfortable in fast-paced, ambiguous environments and wearing many hats.
• 3+ years in account management, CSM, or a client-facing commercial role with technical, complex software solutions.
• Demonstrated success independently renewing and expanding enterprise customers in complex, high-value accounts.
• Minimum bar: negotiated at least one $100k+ deal.
• Enterprise experience managing complex organizations and selling 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.
• Self-directed, proactive, and able to balance empathy with commercial impact.
• Curious by nature, actively learning new domains, products, or systems.
• Hands-on prompt engineering experience: able to optimize AI responses, train conversation flows, and refine model outputs.
• Comfort with a rapidly evolving AI landscape and staying current on AI capabilities.
• Experience with a native AI technology company is a plus.
• Comfort with API integrations, conversation flow design, and business intelligence tools is a plus.
• AI-assisted screening tools are used as part of the hiring process; human decisions are made.
• Request a human-only review at talent@siena.cx.

Skills

• Account Management
• Customer Success Management
• Commercial Acumen
• Executive Relationship Building
• Negotiation
• Sales
• Data Analysis
• Strategic Planning
• Product Knowledge
• Cross-functional Collaboration
• Prompt Engineering
• AI Fluency
• API Integrations
• Conversation Flow Design
• Business Intelligence Tools

Location

• Fully distributed, global team

Work Type

• Full-time
• Remote

Experience Level

• 3+ years in account management, CSM, or a client-facing commercial role
• Enterprise experience

Salary/Compensations

• Great salary plus equity or stock grants

Benefits

• Real ownership with autonomy
• Work that ships and matters
• Opportunity to create a new category
• Globally distributed, async-first, low bureaucracy team
• Learning budget
• Premium AI accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable)
• Quarterly budget for new AI tools

About the Company

• Siena is the Agent of Record for consumer brands, collapsing the stack of disconnected tools into a single agent that owns the entire customer journey on a shared intelligence layer.
• Hundreds of brands already run real customer volume on Siena in production.
• We are a small, fully distributed, global team that leverages our work processes for speed and efficiency.
• We hire athletes: individuals who own outcomes, default to writing, communicate directly, and act decisively.
• We are creating a new category with the Agent of Record, offering unsolved problems and cutting-edge models.
• We are not just looking for people who can do a job, but for those who want to break boundaries, create the future, and reshape industries.

Equal Opportunity

• 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.