Enterprise Account Executive

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. If you want to set the bar rather than follow one, keep reading. THE ROLE 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. WHO YOU ARE The Bar: If you're missing any of these, this isn't the role for you. - 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. "I exceeded quota" tells us nothing. We want to know why you won when others on your team didn't. - Hands-on experience running formal RFP processes in six-figure, multi-stakeholder deals. Strong Signal: Not dealbreakers, but what separates a good hire from a great one. - 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: Bonus, not required. - 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. That 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 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 - 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. 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 talent@siena.cx. Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.