Account Executive - NY

About the role

The role is built for a hunter, someone who thrives in prospecting, navigating complex sales cycles, and turning cold leads into long-term partnerships. This is an opportunity to shape the future with Siena.

What You’ll 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.
• 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.

Who You Are

• 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.

Bonus Points

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

Why Siena?

• 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.
• 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. You 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.

Our Values

• Curious, customer-obsessed, and take ownership without being asked.
• Fix problems first and explain later. Direct about feedback—both giving and receiving it—because they care more about getting things right than being polite.
• 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.
• Adapt and keep pushing forward when things get tough.

Our Approach to AI

• Treat AI like a natural extension of yourself. Build your own ecosystem of agents - some for research, others for debugging, writing, analysis, or writing code.
• 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.

Why Siena?

• We are looking for people who want to break boundaries, create the future, and reshape industries.