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About the Role
Siena is building the intelligence layer for CX at an unprecedented speed. This role is for a closer who treats every deal as the most important, takes initiative, and prioritizes winning through skill over chance. It is designed for individuals who find ways to succeed when others see obstacles.
Responsibilities
- Manage the full enterprise sales cycle from start to close, including multi-stakeholder and multi-SKU deals that can span six months.
- Oversee formal RFP processes, coordinating internal resources like solutions engineering and leadership.
- Exercise complete autonomy in sales interactions, adapting to various stakeholders from CFOs to CX managers without constant check-ins.
- Develop and defend business cases with quantitative data for brands exceeding $100M in annual GMV.
- Identify and capitalize on expansion opportunities within existing deals.
- Maintain a strong point of view on the competitive landscape and develop winning strategies.
Requirements
- Proven track record of closing deals with named brands and specific numbers, specifically accounts with $100M+ GMV.
- Demonstrable quota attainment in the last 1-2 years, with the ability to explain the reasons for success.
- Exceptional executive presence, capable of engaging effectively with a CFO on a cold call.
- Experience managing RFP processes efficiently and effectively.
- A consistent pattern of finding ways to win.
- Prior experience selling usage-based pricing is a plus.
- Prior AI/CX exposure is a plus, but not a requirement if other qualifications are strong.
Skills
- Enterprise sales
- Full sales cycle management
- RFP management
- Business case development
- Expansion sales
- Competitive analysis
- Executive presence
- Negotiation
- Relationship building
- Problem-solving
- Adaptability
- Direct communication
- AI fluency
Location
- Fully distributed, global
Work Type
- Full-time
- Remote
Experience Level
- Not explicitly junior
- Exceptional performers
- Experienced
Salary/Compensations
- Top of market compensation
- Great salary plus equity or stock grants
Benefits
- Equity or stock grants
- Learning budget
- Premium AI tool accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable)
- Quarterly budget for new tools
About the Company
- Siena is the Agent of Record for CX, serving consumer brands like Spanx, FIGS, Brooklinen, and Grüns.
- Siena operates as a connected multi-agent stack on a shared intelligence layer, with agents for sales, support, social media, and voice across the customer journey.
- The team is small, fully distributed, and global, emphasizing leverage in their work processes.
- The company culture values ownership of outcomes, written communication over meetings, directness, and proactive action.
- Siena is creating a new category with the Agent of Record, offering unique challenges and opportunities.
- The company fosters a culture of curiosity, customer obsession, ownership, direct feedback, high standards, and collaboration.
- AI is integrated as a natural extension of work, with a focus on sharing knowledge and workflows.
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.
- The company is committed to a diverse and inclusive workforce and welcomes people from all backgrounds, experiences, perspectives, and abilities.
- AI-assisted screening tools are used, but all hiring decisions are made by humans. A human-only review can be requested.