Account Executive

Meet Siena

Siena is the first intelligence layer for customer experience. Were creating an operating system of AI agents that learn remember and act across every customer touchpointfrom support conversations to shopping experiences to voice and social media interactions.

Siena doesnt just automate support; it powers shopping agents builds persistent customer memory generates actionable business insights and creates empathetic interactions that feel human.

Were transforming how businesses understand and connect with their customers turning every interaction into intelligence that makes the next one better.

The team

Were a small distributed team that punches way above our weight. Every person here has outsized impact because weve built leverage into everything we do. This philosophy makes us faster and frankly more fun to work with.

If youre excited about building something that doesnt exist yet keep reading. Were building agents that dont just respond to customersthey remember them learn from every interaction and connect experiences across channels.

About the Role

As an Account Executive youll be on the front lines of Sienas growth closing high-value enterprise deals and bringing AI-driven automation to the worlds 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.

While weve listed a few preferred locations were flexible as the role is remote. What matters most is your ability to overlap with EST hours and join us in NYC from time to time for in-person collaboration.

What Youll 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 Sienas 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 Sienas AI solutions by aligning our capabilities with customer pain points and business outcomes.

• Consistently exceed quota and revenue targets contributing to Sienas 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

• Meaningful impact. Your work directly shapes our product and company.

• Globally distributed team working at the bleeding edge of CX and AI.

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

• Learning budget. If youre growing so are we.

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

• AI-fluency. Make AI your second nature.

• Tackle unsolved problems. Were redefining how customer experience will look like in the next decades.

Our values

The people who thrive here are curious customer-obsessed and take ownership without being asked. They fix problems first and explain later. Theyre direct about feedbackboth giving and receiving itbecause they care more about getting things right than being polite.

They maintain high standards while moving at startup speed and they build real relationships with teammates because they know thats how great work gets done. When things get tough they adapt and keep pushing forward.

Our approach to AI

The people who thrive here treat AI like a natural extension of themselves. Theyve built their own ecosystem of agents - some for research others for debugging writing analysis or writing code. They 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 others AI workflows.

At Siena were not just looking for people who can do a job. Were looking for people who want to break boundaries create the future and reshape industries. If thats you we look forward to your application.

We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at .

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.

Required Experience:

IC