Account Executive, Siena

• If you're excited about building something that doesn't exist yet, keep reading
• If you have experience selling into enterprise CX, or AI-driven automation, this is an opportunity to shape the future with Siena
• 5+ years of experience in enterprise SaaS sales, ideally in AI, CX, 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
• Highly strategic and data-driven, leveraging insights to optimize deal execution
• 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
• Comfort with rapidly evolving AI landscape by staying current on AI capabilities and applying them to sales motion

Desirable

• We're a small, distributed team that punches way above our weight
• Every person here has outsized impact because we've built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with
• We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels
• As an Account Executive, you’ll be on the front lines of Siena’s growth, closing high-value enterprise deals and bringing AI-driven automation to the world’s top brands
• This role is built for a hunter, someone who thrives in prospecting, navigating complex sales cycles, and turning cold leads into long-term partnerships
• 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
• Work closely with marketing, sales development, and solutions engineering to refine our go-to-market strategy
• Drive adoption of Siena’s AI solutions by aligning our capabilities with customer pain points and business outcomes
• Consistently exceed quota and revenue targets, contributing to Siena’s high-growth trajectory
• Leverage AI tools to scale prospecting, research, and deal preparation
• Build and maintain custom AI workflows for account intelligence, objection handling, and competitive analysis
• Hybrid role based in NYC—expect to be in-office with the team and founders a few days per week