Account Executive

Siena is the Agent of Record for consumer brands. One agent that owns the entire customer journey, running on a shared intelligence layer no point tool can replicate.

Consumer brands run ten or more disconnected tools to manage their customers. We collapse that stack into a single agent. It started with support, the hardest surface a brand has, and it expands from there: Shopping Agent, Social Agent, Siena working alongside a brand's own operators. One agent across every surface, with shared memory, shared context, and shared tools.

Hundreds of brands already run real customer volume on Siena in production. This is built, working, and growing, and we are racing to build what comes next.

We are a small, fully distributed, global team. We have built leverage into how we work, which is what lets a team this size move at the speed we do.

We hire athletes. Everyone here owns real outcomes, defaults to writing over meetings, communicates with directness, and acts the moment they see something worth acting on. Low ego, high standards, fast clock.

If you want to own real problems rather than close tickets, keep reading.

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.

While we've listed a few preferred locations, we're 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 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.

• 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. The Agent of Record is new ground, with unsolved problems and cutting-edge models, not a crowded field to compete in.

• 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. 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.

The people who thrive here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain later. They're direct about feedback—both giving and receiving it—because 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 that's how great work gets done. When things get tough, they adapt and keep pushing forward.

The people who thrive here treat AI like a natural extension of themselves. They've 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 other's AI workflows.

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.

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 [email protected].

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.