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Ariel Cohen: The Death of Salesforce; How OpenAI is Changing the Travel Industry | 20VC #975

Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Ariel has raised over $2BN for Navan from some of the best including a16z, Zeev Ventures, Lightspeed, Greenoaks, and Elad Gil. Prior to TripActions, Ariel co-founded streamOnce, a business multimedia integration platform that was successfully acquired by Jive Software, where Ariel had previously served in a senior position following his time at Hewlett-Packard. ------------------------------------------------ Timestamps: 0:00 Learning New Skills in Today’s World 3:16 Managerial Lesson Learned from StreamOnce 8:55 How to Prioritize Product Development 16:30 How TripActions Bounced Back After COVID Shutdown 20:48 Raising a New Round at a $9.2BN Valuation 28:56 How will your competition respond? 36:08 How Navan Is Using AI & Machine Learning 48:40 How do you define a loyal customer? 51:08 Quick Fire Round ------------------------------------------------------ In Today’s Episode with Ariel Cohen We Discuss: 1.) Why Education is Outdated and Wisdom to People Entering the Working World: Why did Ariel not really attend many classes when he was a student? What would be his biggest advice to young people leaving school today? Where would he focus? Why does Ariel believe that traditional education is more outdated now than ever before? 2.) Why SAP and Salesforce Will Die: Why does Ariel believe that SAP and Salesforce have not innovated for a decade? Why does Ariel believe that Slack is a disaster inside of Salesforce? What are the single biggest advantages that startups have over these large incumbents? What can startups do to retain innovation and speed as they scale into becoming an incumbent? Why are the best founders willing to kill their own projects? 3.) Growing a Business 3x and Raising at a $9.2BN Valuation in COVID: How did Ariel grow the business 3x with all travel being banned? What were the tactics to blitz scaling during COVID? How did Ariel approach his investors for a new round in the middle of COVID? How did he get such a high price in the midst of a global pandemic? What is the bull case for how Navan can be a $40BN company? 4.) Margins Matter: Gaining Leverage Through Additional Margin: With Navan’s 80% margin, they have 30% higher margins than other competitors, how do they have such high margins? With the additional 30%, how does Ariel plan to scale Navan’s reach and use the margin to do so? How does OpenAI play a role in helping Navan increase its margin even further? ------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Ariel Cohen on Twitter: https://twitter.com/@arielcoco Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com -------------------------------- #ArielCohen #navan #tripactions #HarryStebbings #businesswithpleasure #ripbadsoftware

Ariel CohenguestHarry Stebbingshost
Feb 7, 202354mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Ariel Cohen Predicts AI Super Apps Will Kill Legacy Enterprise Software

  1. Ariel Cohen, CEO and co‑founder of Navan (formerly TripActions), discusses how AI and product innovation are redefining business travel, expense management, and enterprise software. He explains Navan’s evolution from a travel tool to an AI-powered T&E super app, including hard decisions like reallocating teams, killing legacy products, and doubling down through COVID when revenue went to zero. Cohen argues that legacy vendors like Salesforce, SAP, Concur, and Amex GBT have structurally lost the ability to innovate and will be displaced by people-centric, AI-native products. He also details how Navan is integrating OpenAI to automate the majority of support interactions, radically improve margins, and reshape the economics of the travel industry.

IDEAS WORTH REMEMBERING

5 ideas

Pick markets with real, proven problems—not just cool technology.

Cohen’s first startup, StreamOnce, failed to make meaningful impact because it targeted a small, unproven problem that nobody urgently needed solved; with Navan, he focused on a massive, obvious pain point—corporate travel and expenses—where demand and budget were already clear.

Continuously kill and rebuild your own products to stay innovative.

Navan repeatedly rebuilt core systems—travel UX, payments, expense, and support—whenever new technology (like modern ML or OpenAI) made older approaches obsolete, even if it meant discarding years of work shortly before launch.

Use hypotheses and hard metrics to decide when to kill or double down on projects.

Cohen frames every new feature as a hypothesis with defined success metrics; if it doesn’t deliver, it gets cut—unless it’s strategically core, in which case they pivot and iterate relentlessly, as they did with Navan’s rewards program until usage finally took off.

In crises, anchor on enduring beliefs and reallocate aggressively around them.

When COVID erased all travel revenue overnight, Cohen revisited his core beliefs (travel will return, T&E is critical, people-centric software wins) and used them to justify layoffs, heavy investment into expense management, continued sales efforts, and fundraising on a “travel will come back” thesis.

AI can transform service businesses into high-margin, scalable software companies.

By using AI and now OpenAI to automate most customer support interactions, Navan has pushed gross margins to ~75% and targets ~80–85%, showing how AI can fundamentally change the unit economics of traditionally low-margin, service-heavy categories like travel management.

WORDS WORTH SAVING

5 quotes

We invented a problem that nobody needed us to solve.

— Ariel Cohen

My nightmare is that one day Navan will be that kind of company—innovating only through M&A and market power.

— Ariel Cohen

By March 2020 it was obvious we had lost product-market fit overnight.

— Ariel Cohen

Nobody is going to use software that makes you fight with your employees all day long.

— Ariel Cohen

Maybe AI is eating the world and eating software, and companies that will not join the party will not be around.

— Ariel Cohen

Founder mindset, learning style, and parenting philosophy about education and explorationChoosing markets, avoiding “invented problems,” and defining strategic focusScaling innovation: killing your own products, project selection, and when to pivot or persistCOVID shock: losing all travel revenue, cost cuts, and doubling down on T&EBuilding Navan as a super app for travel, payments, and expense managementCritique of legacy enterprise software (Salesforce, SAP, Concur, Amex GBT) and their innovation limitsAI and OpenAI integration: transforming customer support, margins, and the travel experience

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