Note: The job is a remote job and is open to candidates in USA. Siena is building an AI-powered intelligence layer for customer experience, serving consumer brands through connected multi-agent solutions. The Enterprise Account Executive will own the full enterprise sales cycle, manage complex RFPs and multi-stakeholder deals, build business cases, and drive expansion within enterprise accounts.
Responsibilities
- 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 the internal resources (solutions engineering, leadership) you'll need to shepherd through them without burning goodwill
- Total autonomy in the room: you 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, because the market is only getting harder and you should already know how you win in it
Skills
- • A 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. "I exceeded quota" tells us nothing. We want to know why you win when other people on your old team didn't
- • The kind of executive presence 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. That's not a personality trait we're hoping for: it's the bar
- • Bonus: a background selling usage-based pricing. If you've sold that way, you already think in terms of land-and-expand and long-term account ownership, not one-and-done transactions
- • Prior AI/CX exposure is a plus, not a requirement, if everything else here is undeniable
Benefits
- Real ownership, with autonomy to solve problems and trust to work without a manager in your inbox.
- Work that ships and matters, reaching real consumer brands fast.
- A globally distributed, async-first team with low bureaucracy.
- Great salary plus equity or stock grants.
- Learning budget.
- Premium accounts for ChatGPT, Claude, Perplexity Pro, Cursor, and Lovable.
- A quarterly budget for new AI tools.
Company Overview