Enterprise Account Executive - Siena

Meet Siena

Siena is the Agent of Record for CX, built for consumer brands like Spanx, FIGS, Brooklinen, and Grüns.

It runs as a connected multi-agent stack on top of a shared intelligence layer: agents that sell, support, listen, handle social and voice across the entire customer journey, turning every conversation into signal you can act on.

The Team

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.

About the Role

Siena is building the intelligence layer for CX, and we're doing it at a speed most reps have never operated at. We are not looking for someone to "manage a territory." We are looking for a closer: someone who treats every deal like it's the only one that matters, who doesn't wait to be told what to do, and who would rather lose a deal swinging than win it by accident.

We're scaling the Enterprise motion and paying for it properly. This is a hunter seat for someone who can walk into a room with a CFO, a CX leader, or a hostile buying committee and command it: no hand-holding, no script, no safety net. You will run six-figure, multi-stakeholder deals with real RFPs and real competitive fire, and you will be expected to operate like you already own the outcome.

We are deliberately not hiring junior reps into this seat. We don't have the bandwidth to coach someone up over eighteen months, and the deals on the table won't wait for anyone's learning curve. We are paying top of market for someone who is already exceptional and wants to prove it again, at a company still small enough that one person's work is visible to everyone.

What You'll Own

• The full enterprise sales cycle, start to close: Multi-stakeholder, multi-SKU, cycles that can run six months and don't move themselves.
• Formal RFP processes: Including shepherding internal resources (solutions engineering, leadership) through them without burning goodwill.
• Total autonomy in the room: Adapt to whoever's in front of you, CFO or CX manager, without checking in at every step, because you already know what to say.
• The business case: Built and defended with real numbers, for brands doing $100M+ in annual GMV.
• The instinct to spot and act on expansion: Inside your own deals, not because it's mandated, but because leaving money on the table isn't in your nature.
• A real point of view on the competitive landscape: Knowing how to win in an increasingly challenging market.

What It Takes to Be in the Room

• A proven track record: Named brands, named numbers, of closing $100M+ GMV accounts. Not "exposure to." Closed.
• Quota attainment: In the last 1-2 years that you can explain, not just report. We want to know why you win when other people on your old team didn't.
• Executive presence: The kind that doesn't need a warm-up. You get on a call cold with a CFO and you already know what to say.
• RFP experience: And the judgment to run one without wasting everyone else's time.
• Hunger: That shows up as a pattern, not a mood. You find a way to win. Every time.
• Bonus: A background selling usage-based pricing (thinking in terms of land-and-expand and long-term account ownership).
• Bonus: Prior AI/CX exposure is a plus, not a requirement, if everything else here is undeniable.

Why Siena?

• Real ownership: 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.
• 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: Premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools.