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 – Trailer
0:53 – Buying process of startups
05:19 – How Zuora’s SaaS portfolio looked 2 years ago
09:00 – Inbound vs outbound
10:53 – How initial contact with potential customers works
13:34 – Startups should be thought partners
16:57 – How long it takes to create value for customers
19:59 – Where startups draw the line in growth vs efficiency
23:06 – Top 5 largest spends
24:01 – Why only 1-year contracts for new AI startups?
26:12 – Why legal & procurement struggle to understand startups
29:46 – 20% of portfolio is 0–5 year old companies
30:46 – Are startups not backed by VCs a red flag?
34:29 – 60% in growth + 40% in day-to-day
37:42 – Learnings from peer CIOs
41:38 – Featurely: Case Study
45:14 – Atomicwork: Case Study
46:55 – Trupeer: Case Study
47:51 – How Zuora uses OpenAI & Anthropic
49:39 – How AI is helping personal productivity
51:26 – How agents will be managed
54:02 – Number of SaaS apps will go down, agents will go up
55:45 – Building the right security for AI
56:31 – India vs US: where founders are building from

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Connect with Siddhartha on:
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Twitter: https://x.com/siddharthaa7

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This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.

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

The Neon Show