Rewind.ai & Optimizely CEO & Founder, Dan Siroker, on augmenting human memory with AI, building Optimizely, AI in operations, privacy and security, hiring and building extraordinary teams, and AI's impact on STEM education

Between Two COO's with Michael Koenig

Dec 5 2023 • 58 mins

(05:11 - 05:38) Memory and the Evolving Digital Age

(06:56 - 08:05) Tech and Memory Retrieval

(11:40 - 12:51) Chat GPT and Data Privacy Integration

(17:34 - 18:44) Leveraging AI for Company Augmentation

(22:34 - 23:47) AI for Efficiency and Exceptional Hiring

(30:31 - 31:01) Pivoting to Capture Meeting Data

(38:38 - 39:00) COO and Chief of Staff Collaboration

(43:27 - 44:27) Using Cultural Values as a Guide

(47:10 - 48:20) Accountability and Candor in Successful Teams

(55:58 - 57:01) Impressions of AI Summarization

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(00:11) Augmenting Human Memory With AI

This chapter of Between Two COOs features a conversation with Dan Sroker, co-founder and CEO of Rewind, a personalized AI tool that augments human memory. Host Michael Kanag explores the inspiration behind Rewind and how it can give users a "superpower" by making all their digital interactions searchable and AI-able. They also discuss the importance of memory and how technology can enhance our natural capabilities. The conversation touches on the potential impact of relying on AI for memory recall and draws parallels to the evolution of phone numbers. Overall, this chapter explores the fascinating intersection of technology and human memory.

(12:51) The Future of AI in Operations

This chapter explores the potential impact of AI on future operations. Our guest, who has experience in scaling a company using AI, discusses how AI can be a powerful tool for leveraging human capabilities and increasing productivity. We also touch on the importance of privacy and security in AI, highlighting how companies that do not embrace it may struggle to compete in the future. The conversation concludes with a discussion on the role of AI in remote work and the potential for smaller teams to achieve more with the help of technology.

(18:44) Enhancing Productivity With Artificial Intelligence

This chapter explores the impact of AI on workplace productivity and efficiency. We discuss the release of GPT-4 and its potential to speed up tasks and increase productivity. Privacy challenges and the importance of employee awareness are also addressed. We examine how AI can bridge the gap between ambiguity and tasks, using Rewind's email summarization feature as an example. The significance of hiring exceptional senior staff and maintaining focus to achieve more with less is emphasized. Lastly, we touch on the potential impact of AI on the job market for recent graduates.

(27:19) The Impact of STEM on Technology

This chapter emphasizes the significance of STEM education in fostering creativity and problem-solving skills through technology. Our guest shares their personal journey with robotics, which led to the creation of innovative products like Optimize-A and Mac. The discussion also highlights the role of M1 and M2 chips in their company's pivot and how it enables local data privacy. Ultimately, we are reminded of the transformative potential of technology and the importance of adapting and maximizing its benefits.

(38:29) COOs and Chiefs of Staff

This chapter explores the dynamics of having a COO and chief of staff simultaneously, and how this partnership can benefit a company. We discuss the importance of screening for a good COO and chief of staff, as well as their role in creating a positive work environment. The former CEO shares his experience of achieving the number one spot for best place to work and the role of psychological safety in creating a fantastic workplace. Overall, this chapter provides valuable insights into the importance of a strong partnership between a CEO and their COO and chief of staff, and how it can contribute to the success of a company.

(42:23) Cultural Values in a Company

This chapter emphasizes the importance of defining and living up to company values. The host, who has experience at Google and now runs his own company, shares insights on creating a strong company culture by clearly defining values and behaviors that align with them. He highlights the need for these values to be a living document, constantly evolving and being used as a basis for performance management. The conversation also touches on the potential pitfalls of using values as a marketing tactic rather than a genuine reflection of the company's beliefs. Overall, this chapter highlights the role of company values in creating a positive and successful work environment.

(45:58) Psychological Safety in Leadership Importance

This chapter explores the importance of psychological safety in creating a successful and cohesive team. We discuss the guest's experience with psychological safety in their previous company and how they are implementing it in their current venture. We emphasize the need for a shared language and vernacular around psychological safety to create a sense of safety within a team. The guest also shares their regrets about not maintaining a balance of comfort and accountability in their previous company as they grew. We highlight the importance of a long-term orientation and hiring slowly to maintain a strong culture. The chapter concludes with the guest discussing their vision for their current venture and their determination to make it their life's work.

(52:03) Ask the Right Question and Succeed

This chapter explores the importance of conducting effective reference checks during the hiring process. We discuss the significance of asking the right questions and building rapport with references to obtain honest and valuable feedback on potential candidates. Additionally, we touch on the game-changing role of AI in the hiring process. The chapter concludes with a discussion on how to handle unexpected moments that may arise in the workplace.