Enterprise Sales Representative (Agent of Record for CX)

Siena is the Agent of Record for CX, built for consumer brands like Spanx, FIGS, Brooklinen, and Grüns. It operates as a connected multi-agent stack on top of a shared intelligence layer, handling sales, support, social, and voice interactions across the entire customer journey, turning every conversation into actionable insights.

What You'll Do

• Build and own your enterprise pipeline targeting ecommerce and consumer brands generating $100M+ in annual GMV.
• Execute the full enterprise sales cycle from initial contact to close, including multi-stakeholder, multi-SKU deals with cycles lasting up to six months.
• Lead formal RFP processes, coordinating with solutions engineering and leadership through each stage.
• Engage with CFOs, CX leaders, and full buying committees, tailoring the business case to each stakeholder.
• Develop and defend the business case with real financial numbers against finance and executive teams.
• Identify and close expansion opportunities within existing accounts.
• Stay ahead of the competitive landscape and articulate how Siena wins in each deal.

Who You Are

The Bar: If you lack any of these, this role isn't for you.

• Experience selling to executive and C-suite stakeholders at ecommerce and consumer brands.
• A track record of closing accounts with $100M+ in annual GMV, including named brands and named numbers. Not just exposure—closed deals.
• Quota attainment or overachievement in the last 1-2 years, with a clear explanation of why you succeeded when others didn’t.
• Hands-on experience running formal RFP processes for six-figure, multi-stakeholder deals.

Strong Signal: Not dealbreakers, but what sets a great hire apart.

• Experience selling AI products or selling into teams adopting AI.
• Sustained quota overachievement across multiple years, not just one standout year.
• A track record of sourcing a meaningful share of your own closed pipeline.

Nice to Have: Bonus, not required.

• Experience selling usage-based pricing with land-and-expand growth inside owned accounts.

Not a Fit If:

• Your experience is primarily in mid-market or SMB with deal sizes below six figures.
• Your closed deals mostly came from inbound leads, not pipeline you created.
• Your enterprise experience is mostly supporting deals rather than owning and closing them.
• This role sounds exhausting rather than exciting to you.

Why Siena?

Real ownership. You’ll own problems, not tasks, with autonomy to solve them your way and trust to act without micromanagement.

Work that ships and matters. Your contributions reach real consumer brands quickly.

Innovation in a new category. The Agent of Record is groundbreaking, with unsolved problems and cutting-edge models.

A team that respects your judgment. Globally distributed, async-first, and low-bureaucracy. We hire adults and treat you like one.

Competitive salary plus equity or stock grants. Own a piece of what you build.

Learning budget. If you’re growing, so are we.

AI-fluency by default. Few places push AI integration further or faster.

Our Values

The people who thrive here are curious, customer-obsessed, and proactive. They fix problems first and explain later. They’re direct about feedback—both giving and receiving—because they prioritize accuracy over politeness.

They maintain high standards while moving at startup speed, and they build real relationships with teammates because they know collaboration drives great work. When challenges arise, they adapt and keep pushing forward.

Our Approach to AI

The people who thrive here treat AI as a natural extension of themselves. They’ve built their own ecosystem of agents for research, debugging, writing, analysis, and coding. They know which AI tools work best for specific problems.

Everyone gets premium AI accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools. The real magic happens through shared knowledge—demo days, Slack threads about workflows, and learning from each other’s AI strategies.

At Siena, we’re not just looking for job performers—we’re looking for boundary-breakers, future creators, and industry reshapers. If that’s you, we’d love to hear from you.