The AI CFO with Alex Wittenberg

In this episode of the Funded, Alex sits down with Sidharth Kakkar, the founder of Subscript, to discuss his journey in raising a $15 million Series A round. The conversation spans various aspects of fundraising, including Sidharth's approach to crafting a compelling narrative for investors, the importance of finding believers rather than trying to change investment perspectives, and the nuances of the delicate relationship between a founder and investors.

Throughout the discussion, Alex and Sidharth emphasize the iterative nature of developing a fundraising strategy and the need to leverage the founder community for guidance. Sidharth's background as a second-time founder informs much of his approach to strategically growing Subscript and successfully navigating the venture capital landscape. This episode offers rich insights for first-time founders aiming to secure venture funding.

Riya Grover, Cofounder and CEO of Sequence, breaks down how AI-powered revenue automation is transforming finance operations for high-growth startups. Companies like Cognition, Deel, and MoonPay are scaling to 9 figures with finance teams of just 3-5 people—and Riya explains exactly how they're doing it.

Riya also reveals the behind-the-scenes story of Sequence's Series A fundraise: how they landed multiple term sheets in just 3 weeks and what investors really want to see beyond the "AI" buzzword. She shares why human-in-the-loop design is the difference between AI that works and AI that creates chaos, plus her framework for building agents that actually integrate into enterprise workflows.

Whether you're building in the AI space, thinking about your next fundraise, or trying to scale your finance operations, this conversation is packed with actionable insights from someone who's doing it at the highest level.

Links & Resources:
• Learn more about Sequence: https://www.sequencehq.com/
• Check out airCFO: https://www.aircfo.com/

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