Enterprise Account Executive

Meet SienaSiena 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 TeamWe 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.This role is not for most people. That's the point.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.If you need a playbook for every situation, a manager checking in on you weekly, or a market that isn't changing under your feet, stop reading now. This isn't that job.If you're the person who finds a way to win when everyone else finds a reason they couldn't, keep reading.What this job actually is 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 ownThe full enterprise sales cycle, start to close: multi-stakeholder, multi-SKU, cycles that can run six months and don't move themselvesFormal RFP processes, including the internal resources (solutions engineering, leadership) you'll need to shepherd through them without burning goodwillTotal 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 sayThe business case, built and defended with real numbers, for brands doing $100M+ in annual GMVThe 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 natureA real point of view on the competitive landscape, because the market is only getting harder and you should already know how you win in itWhat it takes to be in the roomA 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.Why this is worth it This is not a role where you're competing with twelve other AEs for scraps of enterprise pipeline. You'll be one of a small number of people operating at this level, which means your work is visible, your wins compound fast, and you'll help define what "Enterprise AE at Siena" means as the team scales.This is intense. It is also one of the more rewarding seats you'll find: real ownership, real money, and a company moving fast enough that you'll never wonder if your work matters.If that sounds like the environment you've been looking for, we want to talk to you.If it sounds exhausting, this isn't a knock on you, it just isn't this role.Why Siena?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.Our ValuesThe 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 AIThe 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 View email address on click.appcast.io provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex,