How Startups Can Sell to Big Companies Ft. Karthik Chakkarapani, Zuora

If you’re a startup selling to enterprises, understanding how a CIO discovers and evaluates you can change everything. Most founders believe that cold emails and polished decks drive attention, but Karthik Chakkarapani, CIO of Zuora shares that nearly 80% of the startups he evaluates are found through outbound - while researching solutions, through peers, or even on LinkedIn. For many startups, this alone can reshape how they think about go-to-market.How does an enterprise decide whether to buy from a startup or not? Karthik walks us through Zuora’s three-step buying process. It starts with understanding the problem the startup solves and how quickly the product can show value. If the early signals are strong, the next step is a deeper look at ROI, integration, security and whether the company is mature enough to be a long-term partner. The final stage is legal and procurement, which is where many early-stage startups slow down.If you’re building a startup, this episode offers a practical look into how CIOs think, how they make decisions and what it really takes to go from a first conversation to a signed contract.0:00 – Trailer0:53 – Buying process of startups05:19 – How Zuora’s SaaS portfolio looked 2 years ago09:00 – Inbound vs outbound10:53 – How initial contact with potential customers works13:34 – Startups should be thought partners16:57 – How long it takes to create value for customers19:59 – Where startups draw the line in growth vs efficiency23:06 – Top 5 largest spends24:01 – Why only 1-year contracts for new AI startups?26:12 – Why legal & procurement struggle to understand startups29:46 – 20% of portfolio is 0–5 year old companies30:46 – Are startups not backed by VCs a red flag?34:29 – 60% in growth + 40% in day-to-day37:42 – Learnings from peer CIOs41:38 – Featurely: Case Study45:14 – Atomicwork: Case Study46:55 – Trupeer: Case Study47:51 – How Zuora uses OpenAI & Anthropic49:39 – How AI is helping personal productivity51:26 – How agents will be managed54:02 – Number of SaaS apps will go down, agents will go up55:45 – Building the right security for AI56:31 – India vs US: where founders are building from-------------India’s talent has built the world’s tech—now it’s time to lead it.This mission goes beyond startups. It’s about shifting the center of gravity in global tech to include the brilliance rising from India.What is Neon Fund?We invest in seed and early-stage founders from India and the diaspora building world-class Enterprise AI companies. We bring capital, conviction, and a community that’s done it before.Subscribe for real founder stories, investor perspectives, economist breakdowns, and a behind-the-scenes look at how we’re doing it all at Neon.-------------Check us out on:Website: https://neon.fund/Instagram: https://www.instagram.com/theneonshoww/LinkedIn: https://www.linkedin.com/company/beneon/Twitter: https://x.com/TheNeonShowwConnect with Siddhartha on:LinkedIn: https://www.linkedin.com/in/siddharthaahluwalia/Twitter: https://x.com/siddharthaa7-------------This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.Send us Fan Mail