08/21/2026
𝐒𝐞𝐥𝐥𝐢𝐧𝐠 𝐢𝐧 𝐭𝐡𝐞 𝐀𝐠𝐞 𝐨𝐟 𝐀𝐈🚀
Thank you to Reggie Marable, Chief Customer Officer at Sierra, for recently joining us for a sharp fireside chat on how enterprise selling is changing.
Three takeaways we're still thinking about:
1. Earn trust with proof, not promises. Low-commitment entry points and outcome-based pricing make it easy to say yes to something small - then prove your way to a bigger relationship.
2. Engineer credibility early. Respected design partners, founders in the room with early customers, and security and compliance handled head-on build confidence before you have scale.
3. AI accelerates, but people close. The stack is a multiplier for research, prep, and pipeline - but in-person relationship building still closes big enterprise deals