Account Executive (AI)

TL;DR

Account Executive (AI): Own the full sales cycle for high-value enterprise deals, bringing AI-driven automation to top brands with an accent on prospecting, navigating complex sales cycles, and fostering long-term partnerships. Focus on developing strategic outbound motions, managing multi-stakeholder deals, and leveraging AI tools for sales productivity.

Location: Hybrid role based in NYC, expecting in-office presence a few days per week.

Company

Siena is building the first intelligence layer for customer experience, creating an operating system of AI agents that learn, remember, and act across every customer touchpoint.

What you will do

• Own the full sales cycle from prospecting to close, targeting enterprise accounts.
• Build and maintain strong relationships with senior decision-makers in CX, digital transformation, and operations.
• Develop strategic outbound motions to break into top accounts and expand Siena’s footprint.
• Manage complex, multi-stakeholder sales cycles with a consultative and value-driven approach.
• Drive adoption of Siena’s AI solutions by aligning capabilities with customer pain points and business outcomes.
• Consistently exceed quota and revenue targets, contributing to Siena’s high-growth trajectory and leveraging AI tools.

Requirements

• 5+ years of experience in enterprise SaaS sales, ideally in AI, CX, or automation technology.
• Proven success in hunting new business and closing six- and seven-figure deals.
• Skilled in multi-threading enterprise sales cycles and navigating complex organizations.
• Deep understanding of enterprise customer experience, digital transformation, and automation trends.
• Comfortable working in a fast-moving startup environment where adaptability and ownership are key.
• Power-user of AI tools with proven ability to build custom agents/prompts that enhance sales productivity.

Nice to have

• Experience selling AI, automation, or workflow intelligence products.
• Established relationships within executives, CX, eCommerce, or BPOs.
• Experience selling enterprise and multi-product software.

Culture & Benefits

• Meaningful impact, directly shaping the product and company within a globally distributed team.
• Opportunity for equity or stock grants and a dedicated learning budget.
• The thrill of building something new and tackling unsolved problems in customer experience and AI.
• Culture that values curiosity, customer-obsession, ownership, and direct feedback.
• Emphasis on AI-fluency, providing premium AI accounts and a quarterly budget for new tools.
• Collaborative environment for sharing AI knowledge and workflows.