Between Two COO's with Michael Koenig

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Why Linda still codes on weekends — and what it teaches her about the future of AI (6:00)

How AI is changing what Webflow builds — and how fast they build it (3:30–13:00)

What happens when websites are no longer built just for humans (14:00)

The rise of AEO (Answer Engine Optimization) and what it means for ops (17:00–21:00)

Favorite LLMs and workflows — from Claude Sonnet t...

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In this episode, Doug and I cover:

• Why “AI agent” is more than just a buzzword
• The difference between deflection and resolution in AI-powered support
• How Kustomer structures RevOps, GTM, and forecasting
• What it means to operate with high-context vs. generic playbooks
• How Doug thinks about team structure, ownership, and cross-functional clarity
• Predictions for agent-to-agen...

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Key Takeaways:

RevOps aligns and optimizes sales, marketing, and customer success, ensuring efficient and sustainable growth.

Effective RevOps requires balancing strategic planning, data-driven analytics, and tactical execution.

Successful RevOps integration hinges on clear communication, cultural alignment, and strategic hiring decisions.

AI is poised to sign...

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Timestamps:

(02:00) Fellow’s shift from productivity tool to AI assistant.

(07:00) Implementing large-scale organizational change.

(13:00) Managing change and internal communications.

(20:00) Moving toward an agentic, automated workflow future.

(23:00) Unexpected real-world AI uses at Fellow.

(29:00) Privacy, security, and enterprise-grade compliance.

(33:00) Selecting and uti...

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AI and Privacy: Navigating the EU's New AI Act with Flick Fisher

In this episode of Between Two COOs, host Michael Koenig welcomes back Flick Fisher, an expert on EU privacy law. They dive deep into the newly enacted EU Artificial Intelligence Act and its implications for businesses globally. They discuss compliance challenges, prohibited AI practices, and the potential ...

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[00:00] Introduction – Michael introduces Fellow as a trusted AI meeting assistant.
[01:00] Welcome to Between Two COOs – Introducing Justin Etkin and Tropic.io.
[02:00] The evolution of procurement – From cost-cutting to strategic value creation.
[05:00] When should companies start formalizing procurement?
[07:00] Common mistakes busines...

This episode is powered by Fellow AI Meeting Assistant. Get 90 days free at fellow.app/coo

Key Takeaways:

• Hidden C-Suite Job Market: The majority of C-level roles are filled through networking, talent partners, and executive recruiters before job postings are even considered.

• Role of Networking: Building strong relationships within your industry and maintaining top-of-mind positioning with decision-makers is crucial.

• Non-Traditio...

Episode Overview

In this episode of Between Two COOs, host Michael Koenig interviews Jon Mark, COO of Vestwell, a leading provider of digital platforms for workplace savings and investment programs. Vestwell supports nearly 25,000 small businesses, over a million savers, and $25 billion in assets under management across all 50 states.

They discuss Vestwell’s mission to close the savings gap, its innovative approach to financial welln...

In this episode of Between Two COOs, host Michael Koenig sits down with Valentin Gruber, COO of HomeToGo, to explore the inner workings of the vacation rental aggregator and its strategy. HomeToGo went public via a SPAC in 2021, reaching a valuation of $1.2 billion after raising $150 million in VC funding. Valentin shares insights into the company’s growth, its approach to balancing marketplace and software solutions, and the strat...

Navigating Leadership and Innovation at School of Rock with Stacey Ryan

In this episode of Between Two COOs, host Michael Koenig interviews Stacey Ryan, the COO of School of Rock - a global music school franchise. Stacey debunks a common misconception about the business's origin, noting it predated and inspired the 2003 film. She discusses the operational challenges of managing a global franchise, particularly through the COVID-19 p...

Maximizing Meeting Efficiency and Navigating Management Challenges: Insights from Aidan Mizrahi of Fellow

This episode delves into the complexities and potential inefficiencies of meetings in the professional world, emphasizing the staggering number of unproductive meetings held daily. Highlighting the innovative approach of Shopify in canceling recurring meetings to save significant time, the conversation introduces Fellow, a SaaS ...

Presented by Fellow.app. Streamline your meetings and make them more efficient and meaningful. Get Fellow for you and your team today. Head to https://fellow.app/coo/ to get started and start having better meetings.

(00:12) Advice for CEOs and COOs

This chapter welcomes Cameron Harold, the founder of COO Alliance and author of "The Second In Command," as we celebrate the release of his new book and examine its content, which serves...

Could the EU's new AI Act be the cornerstone of global AI regulation? That's what we're here to unpack with the expert insight of Flick Fisher, a leading privacy specialist and partner at Fieldfisher. As the digital age accelerates, the European Union is setting a precedent with the AI Act, a groundbreaking legislation designed to navigate the complex terrain of artificial intelligence. Flick and I dissect the Act's risk-based appr...

Join us as Greg Strickland, COO of Productboard, and I explore the power of embracing new opportunities and the crucial balance between business outcomes and personal advancement. Greg shares his journey of growth through accepting challenges that push boundaries, and we reflect on the times when a strategic 'no' can pave the way for others' development and align with company goals. Listen in for an insightful discussion on the men...

(01:20 - 02:44) The Travel Experience Market's Growth

(04:36 - 06:03) Peer to Peer Tour Guide Platform

(07:27 - 09:26) Learning and Customer Obsession Importance

(12:35 - 13:56) Creativity and Execution in Strategy

(16:11 - 17:06) Identifying Core Values for Company Culture

(21:48 - 23:03) Accelerating Digitization and the QR Code

(36:32 - 37:43) Investment Strategy and Flywheel Approach

(39:48 - 40:47) International Tensions and Investme...

(00:12) Interview With Remote COO Alan Christensen

COO Alan Christensen shares his journey and Duist's success without institutional investment, pioneering remote work and dividing responsibilities with CEO.

(11:48) Future of Remote Work and Communication

Remote work's significance in shaping the future, utilizing asynchronous communication, transparency, and documentation for effective management.

(22:28) Recruitment, Career Growt...

(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 a...

(00:12) Clean Tech and Disrupting Energy Market

(06:15) Community Solar and Renewable Energy Innovation

(15:37) Data Platform and Energy Transformation

(24:21) Acquisitions, Integration, and Board Composition

(29:05) Startup Board Management and Risk Balancing

(35:51) Leadership, Growth Mindset, and Overcoming Challenges

(42:18) Connecting Through Cold Emails

(00:12) Clean Tech and Disrupting Energy Market

We discuss Energy 101 today with...

--------- EPISODE CHAPTERS WITH SHORT KEY POINTS ---------

(0:00:12) - Remote Company Operations and Knowledge Management

Daren explains the importance of low context communication, compounding interest, and over communicating for successful remote teams.

(0:08:59) - Embracing Remote Work as Operating Model

Daren Murph and I discuss operations of successful remote companies, process definition, documentation, culture, macroeconomic d...