Menlo & Oak Advisory
We build with AI.
We operate at scale.
We advise from experience.
Boutique advisory for companies navigating AI transformation, brand strategy, executive coaching, and scalable growth.
Founded by operators,
not consultants.
We've built AI systems, led turnarounds, and managed global brand communications — not from a slide deck, but from the C-suite and the command line.
Menlo & Oak brings Silicon Valley's AI-first thinking to the practical realities of growing consumer businesses across the Americas.
Based in Santiago, Chile — with roots in Menlo Park, California.
Five practices.
One integrated team.
Applied AI & Operational Intelligence
We don't just advise on AI. We build it, deploy it, and use it to run a $230M business. From enterprise chatbots querying SAP to Andrea, a 30+ module Marketing OS for Latin America — we bring AI from theory to production.
Learn more →Retail & Consumer Transformation
Modernize operations, reimagine store formats, and build omnichannel experiences that drive profitable growth.
Learn more →Brand Strategy & Communications
Brands that resonate across borders. Deep expertise in cross-cultural storytelling for the US–LatAm corridor.
Learn more →Growth Advisory & M&A
Inorganic growth, market entry, and investment readiness for retail and consumer businesses.
Learn more →Executive Coaching
High-impact coaching for founders and C-suite leaders navigating transformation. From strategic clarity and decision-making to organizational leadership — grounded in real operating experience, not theory.
Learn more →What they're saying.
Yaneken, Chile's second-largest multi-brand group, wants to keep acquiring: 'We're a retail aggregator'
Read →Sebastián Gebhardt, sneaker collector: 'The most I've paid is two thousand dollars'
Read →Goodbye to bland boards: Diverse corporate governance with a startup mindset for a world that changed
Read →Bold — Sebastián Gebhardt: From Chile's first sneaker store to leading a national retail group
Read →
Sebastian Gebhardt
CEO, Yáneken · Stanford GSB MBA, Arjay Miller Scholar
Leads Chile's second-largest multi-brand retail group ($240M revenue, 158+ stores, 15 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 leads global marketing for Ronald McDonald House Charities. BBA, Universidad de Los Andes (Bogotá); Erasmus, Bocconi.
We've built what
others only advise on.
Operators, Not Consultants
We've managed P&Ls, not just advised on them. $230M+ in revenue, 158 stores, 15+ brands — built from the inside, not a slide deck.
Silicon Valley Meets Latin America
Stanford + Santiago + Barranquilla. Bilingual, bicultural, and built for the US-LatAm corridor. We don't just translate strategy — we bridge worlds.
Results You Can Verify
Our work is public: La Tercera, Pulso, IdDC. We don't hide behind NDAs or vague case studies — we ship outcomes and put our names on them.
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 15+ brands.
Rinde YNK: Expense Management in 5 Days
We built a fully functional expense management platform — replicating 80% of core features from a product acquired for €2.8 billion — in just 5 days. A demonstration that software alone is no longer the moat.
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.
Thinking out loud.
Building in public.
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