Account Executive (Enterprise)

About Siena

Siena is building enterprise empathic AI Agents powered by reasoning-adept LLMs. Siena is the first AI Agent of its kind, designed to integrate with existing systems and interact with customers across multiple channels from a single, unified platform.

If you're excited about the intersection of human-to-machine communication and want to be part of a team driving innovation and making a real impact in automating agentic workflows, join us on our mission to revolutionize customer experience through empathetic AI.

Our values

We’re not about corporate jargon—here’s what truly matters to us:

• Curiosity and creativity: You always seek new knowledge, ask questions, and explore different perspectives to deepen your understanding.

• Customer empathy: You are driven by our customers’ success. You see needs they can’t articulate.

• Resilience: You bounce back from setbacks, adapt to change, and thrive in the face of challenges.

• Ownership and autonomy: When things break, you fix first, explain later.

• Relationships: You create bonds with your colleagues - building trust and sharing success.

• Craft and speed: You balance vision with pragmatism. Your standards pull everyone higher.

• Open and direct: You share and receive feedback. You are open about what’s working and what not.

About the Role

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. If you have experience selling into enterprise CX, or AI-driven automation, 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.

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.

Bonus Points

• Experience selling AI, automation, or workflow intelligence products.

• Established relationships within CX, eCommerce, or BPOs.

Why Join Us

We’re a startup, so no fancy offices or corporate fluff. But here’s what we do offer:

• Make a real impact. Your work directly shapes our product and company.

• A voice that matters. In a small team, every perspective counts—yours included.

• Work your way. Whether it’s from home, a coffee shop, or a moon base—if you're productive, we’re happy.

• Competitive compensation. Great salary plus the opportunity for equity or stock grants.

• Flexible time off. Take at least 15 days—more if you need it.

• A learning budget. If you're growing, so are we.

• The thrill of building something new. Join us at a stage where your contributions matter most.

• Tackling meaningful challenges. We’re redefining how work gets done through AI.

At Siena, we’re not just looking for people who can do a job. We’re looking for people who want to break boundaries, create the future, and reshape industries. If that’s you, we look forward to your application.

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. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.