We think Latin American companies can run on AI as well as anyone's. We're helping them build it.
Advisory from operators, not consultants. Andrea built LATAM Airlines' brand through Chapter 11; Sebastian runs 160+ stores and 10+ brands on AI we wrote ourselves. Everything we recommend has already run on our own P&L.
What we're working on this month.
A living page. We update it every few weeks so you can see what we're actually building, not what we were building when the site launched.
Andrea, the Marketing OS, is past 30 modules and running in production across 8 brands. Alongside it, Meridian — our Bayesian marketing-mix stack — now covers 8 brands across 16 Chilean regions.
Designing Yáneken's 2026 operating plan: how to keep growing inorganically while consolidating the omnichannel operation and taking another point off cost-to-serve.
We take a small number of engagements at a time — there are two of us and no one to delegate to. If you want to know whether we have capacity, the honest answer comes from asking us.
The Retail Brief — one operator question, one answer grounded in data and real deployment. Published bilingually every couple of weeks.
Three core practices. Each one running inside our own company first.
Applied AI & Operational Intelligence
Enterprise chatbots querying SAP and Salesforce in real time. Demand forecasting models in production. Andrea, a 30+ module Marketing OS for Latin America. We write the code, deploy it, and keep it running — then help you build the same capability in-house instead of renting it.
Learn more→Retail & Consumer Transformation
Store formats, omnichannel, and the unglamorous operational detail that decides whether a transformation lands. We've opened stores, closed underperformers, and integrated acquisitions across 10+ brands — so we know which recommendations survive contact with a Monday morning.
Learn more→Growth Advisory & M&A
Yáneken became Chile's second-largest multi-brand retail group through disciplined acquisition. We've sourced the deals, structured them, and done the post-merger integration work that decides whether they ever pay off.
Learn more→Who you actually work with.
Sebastian Gebhardt
CEO, Yáneken · Stanford GSB MBA, Arjay Miller Scholar
Leads Chile's second-largest multi-brand retail group ($230M revenue, 160+ stores, 10+ brands). Combines C-suite retail leadership with hands-on AI engineering — built Andrea's 30+ module Marketing OS as a solo technical founder. Led digital transformation, M&A, and omnichannel strategy at scale. Stanford GSB MBA, Arjay Miller Scholar.
Andrea De Vivo
Assoc. Director Marketing & Comms, RMHC · Former Chief of Brand, LATAM Airlines
Born in Barranquilla, Colombia. Former Chief of Brand & Global Communications at LATAM Airlines, where she led brand strategy across 6+ countries during the airline's most transformative era, including Chapter 11. Recognized as one of LATAM's top 44 leaders out of 700. Now Associate Director of Marketing & Communications at Ronald McDonald House Charities. BBA, Universidad de Los Andes (Bogotá); Erasmus, Bocconi.
Proof of concept.
Proof of speed.
Yaneken: Chile's #2 Multi-Brand Retail Group
Built from scratch through disciplined M&A, operational integration, and AI deployment at scale — an operator-led transformation across 10+ brands.
Rinde YNK: Expense Management in 5 Days
We rebuilt 80% of the core of Rindegastos — the Santiago expense-management platform used by 4,500+ companies — in 5 days, one engineer. Months later Visma acquired it. The point wasn't the software. It was that the software was never the moat.
We still have day jobs. That's the whole point.
Sebastian runs Chile's second-largest multi-brand retail group. Andrea is Associate Director of Marketing & Communications at Ronald McDonald House Charities, after leading brand and global communications at LATAM Airlines through Chapter 11. Menlo & Oak is where that experience goes to work for other companies.
You get the two of us — not a staffed pyramid — and judgment shaped by problems we are still solving on our own P&L.
Based in Santiago, Chile — with roots in Menlo Park, California.
What we believe, and why we can prove it.
Advice you haven't tested is a hypothesis.
We've managed P&Ls, not commented on them. Every recommendation we make has already been tried somewhere it could have cost us money.
The local operator is the edge.
Five of the largest retailers on the planet have failed in Chile. Not for lack of capital — for underestimating the person who lives inside the market. Scale isn't the advantage. Context is.
Software is no longer the moat.
We rebuilt 80% of a real, later-acquired SaaS product in five days with one engineer. What's scarce now isn't the ability to build the tool — it's how many people on your team can actually operate it.
We put our names on the work.
Our record is public: La Tercera, Pulso, Diario Financiero, IdDC. No anonymized case studies, no “a leading retailer.” You can read what we did and see whose name is on it.
Thinking out loud.
Building in public.
Stay in the loop
The Retail Brief — one operator question, one answer grounded in data and real deployment. On AI, retail strategy, and doing business in Latin America. No spam, unsubscribe anytime.
Three phases.
One committed team.
Diagnose
We start by deeply understanding your business, your data, and your ambition. No generic frameworks. No recycled playbooks.
Design
We co-create a strategy that's specific, actionable, and tied to measurable outcomes. Every recommendation grounded in operator experience.
Drive
We stay engaged through implementation. We don't hand off decks — we help you execute, iterate, and ship.
Common questions
What does Menlo & Oak do?
Menlo & Oak is a boutique advisory firm founded by operators, not career consultants. We help companies with AI strategy and deployment, retail and consumer transformation, brand strategy, growth advisory and M&A, and executive coaching — working across Chile, Latin America, and the United States in English and Spanish.
How is Menlo & Oak different from a traditional consulting firm?
Our advisors run real businesses. Sebastian Gebhardt is CEO of Yaneken, a Chilean retail group with 160+ stores and 10+ brands, and builds AI products in production. Andrea De Vivo led brand strategy at LATAM Airlines. We advise from operating experience — deployment and P&L results instead of slide decks.
Who do you typically work with?
CEOs, boards, and owners of mid-to-large retail and consumer companies; family businesses navigating succession or modernization; and leadership teams under pressure to adopt AI who want guidance from people who have actually deployed it.
Do you only advise, or do you also build?
Both. Alongside advisory engagements we build and operate production AI products — synthetic consumer research, computer-vision retail compliance, voice AI, and demand forecasting — deployed across retail, e-commerce, and financial services in Latin America.
Where is Menlo & Oak based?
We operate from Santiago, Chile and Menlo Park, California, and serve clients across Latin America and the US, fully bilingual in English and Spanish.
How does an engagement start?
With a conversation, not a proposal. Book a consultation through our calendar or email andrea@menloandoak.com — we'll discuss your situation and tell you honestly whether and how we can help.
What they're saying.
Yaneken, Chile's second-largest multi-brand group, wants to keep acquiring: 'We're a retail aggregator'
Read →AI: evolving is not optional for those who work in and lead companies
Read →#162 — Artificial Intelligence in Retail, with Sebastián Gebhardt, CEO of Yáneken
Read →The graveyard of giants: why global retail fails in Chile
Read →The discount mirage: why retail is digging its own grave
Read →The country where giants fall: why global retail fails in Chile
Read →- Señal DF—Beyond the anchor stores: the owners of specialty fashion retail in Chile
- DF MAS—Grupo Yáneken acquires urban magazine Joia
- América Retail—The dogmatism of efficiency
- The Clinic—'An elevated curation': Grupo Yáneken lands in MUT with a Drops store
- IdDC—Goodbye to bland boards: Diverse corporate governance with a startup mindset for a world that changed
- MAS Que Un Pitch—Bold — Sebastián Gebhardt: From Chile's first sneaker store to leading a national retail group
- La Tercera · Domingo—Sebastián Gebhardt, sneaker collector: 'The most I've paid is two thousand dollars'
Let's Build Something Together
Whether you're a retailer ready to transform, a brand entering new markets, or a company looking to put AI to work — we'd love to hear from you.
Or email us directly at andrea@menloandoak.com