Account Executive

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.

Responsibilities

• 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.

Requirements

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.

Qualifications

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

Skills

Power-user of AI tools, comfortable with rapidly evolving AI landscape, strategic and data-driven, able to build custom agents/prompts, multi-threaded enterprise sales cycles, deep understanding of enterprise customer experience, digital transformation, and automation trends.

Benefits

Real ownership, autonomy to solve problems your way, work that ships and matters, learning budget, AI-fluency by default, premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable), quarterly budget for new tools, demo days, Slack threads about AI use cases, sharing knowledge within the team.

Pay

Competitive salary plus equity or stock grants.

Schedule

Remote, but with occasional in-person collaboration in NYC to overlap with EST hours.