How Founders Should Sell to Enterprise | TinyFish x Airwallex

How Founders Should Sell to Enterprise is a 1-hour-18-minute fireside chat recorded at TinyFish GTM Academy in San Francisco and released in September 2026. The session is built for founders who are selling right now and wondering whether enterprise is worth it, and it pairs two people who have done enterprise sales at scale. Sudheesh Nair, co-founder of TinyFish, ran sales at Nutanix and was CEO of ThoughtSpot. Philipp Reichardt is VP, Enterprise, Americas at Airwallex.

Between them, they answer the questions founders ask most: whether a startup should sell to enterprise at all and what it costs, why sorting customers by high touch versus low touch works better than enterprise versus mid-market, where the first customers come from and why a competitor's conference is the next place to go, and how to test whether a champion is real before the deal depends on them.

The second half gets tactical. Sudheesh and Philipp cover how to answer "what does it cost?" on a first call without negotiating against yourself, the difference between hard dollars and soft dollars and how to help a champion defend the deal to a CFO, when to push a stalled deal to a clear yes or no, and when to hire the first sales rep.

JY Studio recorded the full session on location, with multi-camera coverage of both speakers and clean microphone audio for each, so a long-form talk stays watchable end to end and can be cut into short clips for social. This is JY Studio's second production with TinyFish, after the TinyFish x Glean partnership interview, and it also connects to JY Studio's work with Airwallex, including the T:0 walk-and-talk and the SF Giants suite day at Oracle Park.