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Siena AI careers: remote jobs, culture and where they hire

Empathic AI agents for consumer brands, built by a small remote team that hires athletes.

Team of 73$11.1M total fundingBacked by Sierra Ventures and Aglaé VenturesHiring remotely across the United States, Canada, Europe and Latin America

Who backs Siena AI

Siena AI has raised roughly $11M across two rounds. A $4.7M seed announced in November 2023 was led by Sierra Ventures, with Pari Passu Ventures, Spacestation Investments, Village Global, The Council, OpenSky Ventures and SuperAngel.Fund participating; Tracxn puts the post-money valuation at about $7.6M. A second, unannounced seed round of about $6M to $7M closed in mid 2024 with Aglaé Ventures, the venture firm of LVMH founder Bernard Arnault, and co-founder Lisa Popovici has since described raising more than $10M from investors including LVMH's fund, Sierra Ventures and The Council. Sierra partner Tim Guleri wrote that the firm was hunting for "a vertically focused Generative AI company with self-learning and multi-modal capabilities" and that the founders "had built something really impressive." The $350K pre-seed from GapMinder VC that databases attach to Siena was the 2020 Cartloop round.

What is Siena AI?

Siena AI builds AI agents that run customer experience for consumer brands: a Customer Service Agent that handles support across email, chat, SMS and social DMs in more than 100 languages, plus Shopping, Social, Reviews and QA agents, Voice, Order Protection, a Docs knowledge layer, and Ask Siena, an agent for the operators behind the brand. The company calls the goal the "Agent of Record for CX": one system with shared memory across every surface instead of the ten or more disconnected tools a brand typically runs. It integrates with Shopify, Gorgias, Zendesk, Kustomer, Recharge and Yotpo, tracks orders across more than 2,000 carriers, and says brands using it automate up to 80% of customer interactions.

Siena started in 2022 when the founders' previous product, the Shopify SMS marketing app Cartloop, pivoted into autonomous customer service after ChatGPT launched. Six months after launch it had 65 customers including Kitsch, Simple Modern and Everyday Dose; the careers page now says hundreds of brands run real customer volume on Siena in production, and postings name Spanx, FIGS, Brooklinen and Grüns. Infant formula brand Bobbie chose Siena as the operating system for its care team in June 2026, and skincare brand Dossier used it through Black Friday. The team is around 70 people.

Who founded Siena AI

Andrei Negrau, CEO and co-founder. Serial e-commerce founder from Oradea, Romania: ran his own Shopify brands from 2014, founded the Shopify app Relevon in 2019, then co-founded and led Cartloop, the SMS marketing platform that raised EUR 300,000 from GapMinder VC in 2020 and pivoted into Siena in 2022. Angel investor in Gumloop (YC W24). Studied at the University of Oradea (2012 to 2016). Based in New York.

Lisa Popovici, President and co-founder. Trained as a doctor at the University of Medicine and Pharmacy in Oradea (2013 to 2019) while building and exiting two Shopify fashion brands, then co-founded Cartloop with Andrei as Head of Growth, COO and CMO. Was Siena's CMO before becoming President, was named to Forbes 30 Under 30, and went through Y Combinator's Startup School in 2019. Based in New York.

Where does Siena AI hire remotely?

Siena AI is a fully remote company headquartered in New York, with a second office in San Francisco, that hires across the United States, Canada, the United Kingdom, Europe and Latin America. Current postings list New York, Boston, Chicago, Austin, Miami, Atlanta, Toronto, Montreal, London, Lisbon, Helsinki, Bucharest, Tallinn, Riga, Spain, Poland, Buenos Aires, São Paulo, Rio de Janeiro and Mexico City, and the team already spans 15 countries including Romania, Poland, Moldova and New Zealand.

United Kingdom: 7 open rolesEurope: 5 open rolesUnited States: 2 open rolesLatin America: 2 open roles

Open remote jobs at Siena AI

Describe your next role, cut the noise

Why Siena AI is exciting to work for

Siena AI ships to production customers every week. The careers page puts it plainly: "What you build here reaches their customers the same week. The system is live, people depend on it, and it is nowhere near finished." Postings list Order Protection, Social Agent, Voice and Shopping Agent all spinning up in parallel, several product launches are planned back to back over the next two quarters, and the content and creative roles are explicitly founding seats where the founders review your work directly and nothing is diluted by committee.

Every employee runs their own AI stack on company-paid accounts. Postings say everyone gets premium ChatGPT, Claude, Perplexity Pro, Cursor and Lovable accounts plus a quarterly budget for new tools, and the team shares workflows through demo days and Slack threads about which model fits which job. Patricio, a new deployment hire, said in August 2026 that "AI-first at Siena isn't a tagline, it shows up in how non-technical teams instinctively reach for AI reasoning before anything else."

The company is small enough that ownership is real. The careers page says the size only holds "while everyone here owns a real outcome," the Engineering Manager posting admits the whole platform's context is currently bottlenecked in one person and hires someone to take 30% of it, and the Director of Strategic Accounts role reports straight to the CEO with a book of accounts paying $100K+ in ARR. Recruiting lead Sam Rowland, a month in: "ownership isn't just a value on the wall here, it's something you feel from day one."

Siena AI vibe check

Hours
Flexible working hours is a listed benefit, but customer-facing roles set overlap rules: the Solutions Engineer posting requires overlapping hours with US Eastern time, and Product Specialist asks for a base in EMEA or North America for timezone crossover.
Time off
Unlimited PTO with a minimum of 15 days off a year; an earlier Senior Fullstack Engineer listing phrased it as "Take at least 15 days, more if you need it."
Office
Fully remote with no required office: the careers page says "No headquarters, so nobody's timezone is the one that counts," and account managers travel for in-person workshops and QBRs.
Pace
Intense by the company's own description: the creative director posting says "This is intense, real ownership, real launches, a founder team that reviews your work directly," Sam Rowland called the pace "relentless" in May 2026, and Welcome to the Jungle shows a Glassdoor score of 3.4 (2026).
Equity
Every posting offers "great salary plus equity or stock grants," plus a learning budget.

What to expect from the culture

Siena AI names six traits it hires for: curiosity and creativity, customer empathy, resilience, ownership and autonomy, relationships, and craft and speed. The shorthand is "We hire athletes," and every posting expands it the same way: "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." The people who thrive "fix problems first and explain later" and are "direct about feedback, both giving and receiving it, because they care more about getting things right than being polite."

The founders warn off people who want structure. Lisa Popovici and Andrei Negrau sign the careers page with: "If you want a defined lane and a roadmap handed to you, we will frustrate you. If you would rather take a problem nobody has solved yet and carry it all the way to the end, we should talk." Postings carry a "Not a fit if" list: wanting tickets assigned with a clear spec, needing a manager checking in to stay motivated, needing a fully defined process to operate, or doing your best work "on a slow, considered, one-project-at-a-time pace." Being anti-AI is listed as disqualifying for the creative director role.

The counterweight is that people describe it as kind. Carla, another 2026 deployment hire, said what stood out was "how much thought goes into everything we do, from the product to how we approach customers, while keeping such a genuinely kind and collaborative culture," and postings promise "the trust to do it without a manager in your inbox" and that "we hire adults and treat you like one."

How to get hired at Siena AI

Siena AI runs hiring on Ashby and screens for ownership and AI fluency before anything else: postings ask whether you already build with Claude, Cursor or v0 daily, and non-technical roles such as talent operations state that using Claude to run the work "isn't optional here." Candidate reports on Glassdoor, as summarised by Woody Jobs in September 2026, describe four stages: a recruiter call, a hiring manager interview, a founder interview, and a trial week that tests collaboration in both directions. Sales and customer-facing loops include a practical exercise built on real scenarios.

The company discloses that it uses AI-assisted screening tools, that all decisions are made by humans, and that you can request a human-only review by writing to talent@siena.cx. Postings often separate "The Bar" (missing any item means the role is not for you) from "Strong Signal" and "Nice to Have", so read the bar list literally before applying.

Siena AI hiring FAQ

How much does Siena AI pay?

Siena AI publishes pay on only some postings: the London Talent Ops Specialist contract shows $60K to $80K, pro-rated for its six-month term, and an earlier Senior Fullstack Engineer listing topped out at $220,000. Other roles say "competitive base salary plus equity" and size compensation to experience. Glassdoor reviewers have flagged pay differences between people in similar roles because of location, so ask for the band for your country early.

How long does the Siena AI interview process take?

About 16 days on average from application to decision according to candidate reports on Glassdoor, and two to four weeks in the Dataford interview guides, which describe long conversational screening calls and rate the process as medium difficulty across 13 reports. The trial week at the end is the stage to plan time for.

What is Siena AI's tech stack?

Siena AI does not publish its full stack. The product is built on large language models with its own reasoning engine, prompts, knowledge bases and retrieval, and engineering postings expect you to have built or debugged LLM workflows and to know where they break between test and live. Platform work centres on webhooks, OAuth flows and integrations with Shopify, Gorgias, Zendesk, Kustomer, Recharge, Yotpo and Meta.

Does Siena AI hire juniors or interns?

Not at the moment. There are no internship listings, senior roles ask for three to five or more years of experience, and the closest entry points are the Product Specialist role, pitched at people who "want into product, fast and deep," and a six-month fixed-term Talent Ops contract in London.

Does the Siena AI team meet in person?

Yes, mostly around customers. The founders host a monthly AI Lab dinner for CX leaders, so far in New York, Los Angeles, San Francisco and London, and brought operators to a private product event in New York in May 2026. No company-wide offsite schedule is published.

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