Siena AI
Founding Creative Director
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Meet Siena
Siena is the 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
Siena is building the intelligence layer for CX, and we're about to launch several products in quick succession. We are not looking for someone to execute a brief well. We are looking for the person whose taste the rest of the company gets measured against: someone who looks at a landing page and can't not have an opinion, who would rather kill a launch than ship something mediocre, and who has owned creative direction before, not just contributed to it.
If you need a creative director above you setting the vision, a team to delegate to on day one, or a slow, considered, one-project-at-a-time pace, stop reading now. This isn't that job.
If you're the person other designers already defer to on taste, continue.
This is a craft title. Not a headcount title.
You will ship personally for the first year and set the bar for everyone who comes after. Over time you will build a small internal agency, two to three people across design, motion, and content, that can brief, position, and launch without outside help.
Narrative and positioning across every launch - design as strategy, not decoration
- Every artifact that goes to market: landing pages, launch video, decks, social
- The design system, from v3 onward
- The bar, full stop - if it ships under the Siena name, you made it or you signed off on it
What it takes to be in the room
- Taste, above everything, and evidence you can defend it. Specific, defended opinions about what's good and why.
- A track record of owning creative direction, not just contributing to it. Agency or in-house, brand refresh or full launch - you've been the person whose call was final, not the one waiting on notes.
- Narrative thinking. Design as positioning. You should already have a point of view on how a brand like Siena should be positioned, not just how it should look.
- AI as a working tool, not a threat to your taste. You've already built something with AI - an app, a prototype, a mockup - and you want to get technical enough to ship a landing page yourself within a year. Anti-AI is disqualifying.
- Range that travels. Your background doesn't have to be SaaS. Fashion, art, consumer brand, editorial - what matters is whether your taste holds up somewhere new.
- A pattern of shipping in chaos, not around it. Multiple launches in flight, feedback that moves in hours not weeks. If your best work happens on a slow, protected timeline, that's useful information - it's just not this role.
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Why this is worth it
You're not joining a design team to fit into. You're setting the taste bar for a company that's about to be a lot more visible, a lot faster than most companies get that chance.
This is intense - real ownership, real launches, a founder team that reviews your work directly and moves at the pace you'd expect from that. It's also one of the rare creative seats where nothing you make gets diluted by committee before it ships.
If that sounds like the room you've been trying to get into, we want to talk to you.
If it sounds like too much scrutiny too fast, 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.
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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 workflow. 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.
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.
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.
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