[Hiring] Enterprise Account Executive @Siena AI

Role Description

This role is not for most people, and that's the point. Our Enterprise customers are ecommerce and consumer brands doing $100M+ in annual GMV, and this seat is for someone who has already closed deals at that level. This is a hunter seat: you'll build your own pipeline and take six-figure, multi-stakeholder deals from first call to signature, with real RFPs and real competitive pressure. It's not built for junior reps: the deals are complex and the bar is high from day one. We want someone with a proven enterprise record who wants to do it again, at a company small enough that every win is visible.

What You'll Do

• Build and own your enterprise pipeline into ecommerce and consumer brands doing $100M+ in annual GMV.
• Run the full enterprise sales cycle from first conversation to close: multi-stakeholder, multi-SKU deals with cycles that can run six months.
• Lead formal RFP processes, coordinating solutions engineering and leadership through each stage.
• Run executive conversations with CFOs, CX leaders, and full buying committees, tailoring the case to each stakeholder.
• Build the business case with real numbers, and defend it with finance and executive teams.
• Find and close expansion opportunities inside your own accounts.
• Know the competitive landscape and how Siena wins in it, deal by deal.

Qualifications

• Experience selling to executive and C-suite stakeholders at ecommerce and consumer brands.
• A track record of closing accounts doing $100M+ in annual GMV, with named brands and named numbers. Not "exposure to." Closed.
• Quota attainment or overachievement in the last 1-2 years that you can explain, not just report.
• Hands-on experience running formal RFP processes in six-figure, multi-stakeholder deals.

Requirements

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

Nice to Have

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

Not a Fit If

• Your experience is mainly mid-market or SMB, with deal sizes well 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 sounds exhausting rather than exciting.

Benefits

• 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.
• A team that respects your judgment. Globally distributed, async-first, low bureaucracy.
• 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.

Our Values

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.

Our Approach to AI

The people who thrive here treat AI like a natural extension of themselves. They've built their own ecosystem of agents for various tasks. Everyone gets premium accounts plus a quarterly budget for new tools. Knowledge sharing is key, with demo days and collaborative discussions.

How We Hire

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].