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Co-founder and CEO of Ramp Eric Glyman shared his operating playbook for leading one of the fastest-growing startups on his second appearance on the podcast. We also explored the unique ways Ramp leverages AI internally, strategies for startups to build moats in AI, and the concept of self-driving money. We concluded with one of the most profound and thoughtful discussions about hiring, motivations, and success. It was truly enjoyable to sit down with a seasoned portfolio founder—here are some takeaways… → Ramp’s AI Sales Assistant No person has the time to listen to 50,000 sales calls, but a large language model can. Ramp built an internal Slack bot, Toby, in a weekend, allowing SDRs to ask questions like why customers prefer Ramp over competitors or customer opinions on new features. Toby processes this information in seconds, providing summarized insights from hundreds or thousands of transcripts and helping sales reps do their jobs better. → Interviewing for Curiosity Eric prioritizes hiring for curiosity. To analyze this, ask candidates about a particularly successful project, then ask what they might do differently now. The level of detail in their response will reveal their involvement in the project and their ability to reflect on past experiences, indicating whether they constantly seek improvement. The great ones will be able to go through every level of detail with a high level of specificity. Additionally, ask about their favorite books or recent deep dives outside of work to uncover further curiosity. → The Power of Simple Marketing You have about 5 seconds to deliver a message that is simple, direct, and compelling enough to make prospects want to learn more. Startups often face the challenge of overcoming indifference and getting people to care about their products, as potential customers disregard new products unless they capture attention quickly. So, you must deeply understand what drives customers to spend their time and money to create effective messages. → Don’t Overlook Employees’ Long-Term Goals Organizations often overlook understanding their employees' motivations and long-term goals. However, everyone is the hero of their own story, so it's crucial to periodically check in with employees to see if they are progressing toward their professional aspirations. Hold employees accountable for their main tasks but also ensure they work on problems that can help them progress toward their career goals for higher team motivation. Check out the full episode here: https://lnkd.in/d-3JwzJD