Last updated: September 2026
Most AI companies write job posts that hedge. Siena AI wrote one that tells you to stop reading.
Its Founding Creative Director listing, live on Woody since September 2026, contains a line that almost no design job in Europe has dared print: "Anti-AI is disqualifying." It also says, plainly, "This is a craft title. Not a headcount title." If you are a creative director who has spent two years quietly deciding how you feel about generative tools, this posting is a mirror.
That is the reason Siena is worth a serious look right now. Not because it is the biggest AI company hiring designers, it is not. Because it is one of the few asking for a specific kind of creative person, saying so out loud, and handing that person the entire brand.
What Siena AI actually does
Siena calls itself the Agent of Record for CX. In practice, it is an AI-native customer experience platform built for consumer and DTC brands, replacing the ten or more disconnected tools a brand normally runs to talk to its customers.
It started with support, then expanded into a connected multi-agent stack: a Customer Service Agent, a Shopping Agent, a Social Agent, a Reviews Agent, a QA Agent, plus intelligence products like Topics Explorer and Ask Siena. All of it sits on one shared memory and context layer, which is the part competitors using bolt-on chatbots cannot easily copy.
The customer list is the credibility. Spanx, FIGS, Brooklinen, HexClad, Allbirds, Coterie, Thrive Causemetics, Kitsch and GrΓΌns all run on it. The Spanx case study is the most useful public number available: Siena handles 50% of Spanx conversations, average handle time has been cut in half, and CSAT is up five to seven points (Siena AI customer story).
On funding, Siena is deliberately lean. It raised a $4.7M seed in November 2023 led by Sierra Ventures, with Village Global and others (Siena AI blog), and public trackers put total funding at roughly $11M to $12.7M across three rounds (PitchBook, Crunchbase). Headcount sits around 70 people, up 27% year over year as of August 2026 (Crustdata).
The founders are Andrei Negrau, co-founder and CEO, and Lisa Popovici, co-founder and president. Both are Romanian, both are second-time founders out of conversational commerce, and both still write the company blog and run the AI Lab events themselves. That matters for a creative hire, because the job post says your work gets reviewed directly by the founder team.
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What it is like to work there
Siena is fully distributed, async-first, and writes before it meets. The company describes itself as small by choice with "leverage built into how we work," and the language it uses about people is unusually blunt: "We hire athletes," "low ego, high standards, fast clock," "we hire adults and treat you like one."
The AI ritual is the genuinely distinctive part. Every employee gets premium accounts for ChatGPT, Claude, Perplexity Pro, Cursor and Lovable, plus a quarterly budget for new tools. The team runs demo days where someone shows a clever workflow, and Slack threads comparing which model handles which use case best. The stated expectation is that you arrive with your own ecosystem of agents for research, writing, debugging and analysis, not that you learn one on the job.
For a creative director specifically, the brief goes further. Siena wants someone who has already built something with AI, an app, a prototype, a mockup, and who intends to get technical enough to ship a landing page personally within a year.
The honest counterweight: Glassdoor reviews are mixed. Employees consistently praise the autonomy and the absence of micromanagement, and at least one review calls it "the best remote workplace so far." Others flag a founder who can be stubborn, and pay discrepancies between people in similar roles because of location (Glassdoor). Read both sides before you apply.
The hiring process
Siena documents more of its process than most companies this size. Candidate reports on Glassdoor describe four stages: a recruiter call, a hiring manager interview, a founder interview, and a trial week. The trial week is the part to plan for, and interviewers apparently raise it repeatedly. It exists to test collaboration in both directions.
Average time from application to decision is about 16 days across all roles (Glassdoor).
Siena also discloses that it uses AI-assisted screening tools, with all final decisions made by humans, and it publishes an address where you can request a human-only review. That transparency is rare, and worth noting if AI screening is something you object to.
Salaries, and what Woody's data actually shows
Here is the part nobody else can tell you. Across the Siena roles published on Woody, including the Founding Creative Director and the Senior Product Marketing Manager, Siena posts no salary band at all. The job copy promises "great salary plus equity or stock grants," which is not a number.
So use the Woody comparison set instead. Among senior brand and creative roles currently live on Woody, the visible bands cluster tightly:
- Senior Brand Designer at Norm Ai, US remote: $150k to $200k
- Senior Director, Brand at Airalo, UK remote: $150k to $200k
- Associate Creative Director at Avalere, US remote: $150k to $200k
- Senior Manager, Art Direction at Depop, US remote: $150k to $200k
- Director, Brand and Communications at Kickstarter, US and UK remote: above $200k
A founding creative director with full sign-off on everything shipping under the company name sits at or above that Kickstarter tier in scope, even if the European base will land lower than a US equivalent. Public salary data on Siena itself is thin: Glassdoor lists only 7 salaries across 6 job titles, and Levels.fyi has a company page with no meaningful design compensation entries. Treat the range as negotiable and go in with the Woody comparables in hand.
One more Woody signal worth reading: Siena's creative hire is filed under Brand Design, not Product Design. The first serious design investment here is narrative and positioning, not interface work. The two live roles are also geo-split, the creative seat is UK and Europe, the marketing seat is US, both remote and full-time.
Should you apply?
If you want a design team to slot into, no. If you are the person other designers already defer to on taste, and you have been waiting for a seat where nothing gets diluted by committee, this is one of maybe five jobs in Europe that fits.
Browse Siena's live roles on its Woody company profile, and if nothing fits today, set a job alert so the next AI and brand design roles reach you first.
FAQ
What does Siena AI do? Siena is an AI-native customer experience platform for consumer and DTC brands, positioning itself as the Agent of Record for CX. It runs a connected stack of agents across support, shopping, social, reviews and quality assurance on one shared intelligence layer.
Is Siena AI remote? Yes. Siena is fully distributed and async-first. Both roles published on Woody are remote and full-time, with the creative role open to the UK and Europe and the marketing role to the US.
What is the Siena AI hiring process? Four stages according to candidate reports: recruiter call, hiring manager interview, founder interview, and a paid trial week. Average time to decision is around 16 days. Siena uses AI-assisted screening but states all decisions are made by humans.
What does Siena AI pay designers? Siena does not publish salary bands on its Woody listings. Comparable senior brand and creative roles on Woody sit at $150k to $200k, with director-level brand roles above $200k. Public data on Siena specifically is limited to a handful of Glassdoor entries.
How much has Siena AI raised? A $4.7M seed in November 2023 led by Sierra Ventures, with total funding reported between $11M and $12.7M across three rounds. Headcount is around 70, up 27% year over year as of August 2026.
Which brands use Siena AI? Spanx, FIGS, Brooklinen, HexClad, Allbirds, Coterie, Thrive Causemetics, Kitsch and GrΓΌns, among hundreds of others running production volume.
