Get Brad's new book, Give First.

00:00 — Cold open: “Something new is fucked up in my world every day”

02:00 — The Yoda t-shirt story + the mythology of Brad Feld

04:00 — “Give First” vs. “Pay it Forward”: philosophy, not obligation

07:00 — Why giving isn’t altruism — and how it works in complex systems

10:00 — Positive-sum vs. zero-sum: tennis, trust, and long games

13:00 — Does giving create outcomes, or just energy?

16:00 — Why Brad writes books: longform thinking as meaning-making

20:00 — Searching for meaning through mentorship and reflection

23:00 — “I hate the phrase pattern recognition” — mentorship done right

28:00 — The power dynamic between founders and mentors

32:00 — Management through commitment, not control

35:00 — Agile as an operating system for accountability

38:00 — Emotional intelligence and the role of executive coaches

41:00 — Mentor vs. coach vs. therapist vs. advisor

45:00 — Trust as the foundation of all high-leverage relationships

47:30 — Wild story: when the second floor of Sphero’s building collapsed

52:00 — “They can’t kill you and they can’t eat you” – Len Fassler’s advice

55:00 — Closing thoughts on being the Bill Murray of venture capital

This episode goes deep into the mechanics of scaling a company from steady growth to breakout velocity. Peter shares how Spreedly quadrupled ARR growth in his first year without increasing OPEX, why the “right people pointed at the right problems” is everything, and how to decide which problems are existential versus learn-as-you-go.

We dissect how go-to-market organizations evolve from $20M to $100M ARR, the power of focus and role separation, and how to keep silos aligned around one customer story.

Peter also explains the shift from “payments orchestration” to “open payments” and how Spreedly’s position as the original player in the space gives them unique leverage. We walk through the future of agentic commerce, Google’s new agent-to-agent payments protocol, and what it means when agents can transact faster than any human could ever shop.

We close out with the Dodgeball acquisition, a primer on fraud orchestration, and a wild story about working an entire night shift at a nightclub during a meltdown launch.

Topics Covered:

• How Peter defines the journey to presidency
• The “right person, right problem” framework
• One-way vs two-way doors for staffing big problems
• How to scale a GTM org from $20M to $100M
• Why open payments replaces orchestration
• Spreedly’s unique market position and 15-year head start
• Agent to agent commerce and Google’s new payments protocol
• How AI changes the velocity of money movement
• Fraud orchestration and Spreedly’s acquisition of Dodgeball
• Balancing profitable growth vs growth at all costs
• Perception vs reality in leadership
• Peter’s wildest “I never thought I’d see that” story

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This week on Between Two COOs, Michael sits down with Harris Clarke, COO at GuideCX, to talk about what steady leadership actually looks like inside fast-changing companies.

Harris started his career in protocol and operations for the U.S. Department of State, where “process” wasn’t just a buzzword — it was survival. He shares how those lessons translate to running a modern SaaS organization and why purpose, process, and payoff are the anchors of any good meeting.

They dig into:

• How government discipline shaped Harris’s operating style
• The “three P’s” framework for productive meetings
• Why decision speed is overrated — and what Harris means by “Did anyone die or go to jail?”
• What he learned from executive coaching and board feedback
• How GuideCX built a new product category around customer onboarding
• How AI is quietly reshaping how he manages teams and prepares communications
• Why calm is a competitive advantage during crisis moments like SVB

Michael also gives context at the top: this episode was recorded across two sessions, after a recording issue mid-interview (and yes, he’s now officially a Riverside convert).

It’s a conversation about building trust, running tight systems, and keeping your head when everything around you is changing.

Harris Clarke on LinkedIn
GuideCX

Michael Koenig on LinkedIn

Between Two COO's Website

Episode Website

From Zocdoc to Cascade, COO Anna Elwood breaks down the systems, rhythms, and AI tools that turn chaos into execution.

In this episode of Between Two COOs, Michael sits down with Anna Elwood, COO of Cascade, the strategy-execution platform helping companies turn plans into results.

Anna shares how she evolved from Broadway actor to operator, scaling companies like Zocdoc, Knotel, and Teachable before joining Cascade to build the muscle of strategy execution.

She explains how to create an “operating rhythm” that keeps teams aligned across time zones, the tension between governance and red tape, and how Cascade helps leaders link vision to measurable execution.

The conversation dives deep into AI’s role in operations, the future of hybrid work, and what it takes to move from chaos to clarity in a global startup.

Anna’s storytelling — especially her account of leading through Superstorm Sandy — highlights what real-time operational leadership looks like when everything goes sideways.

Timestamps

00:00 – Intro & sponsor

01:00 – The chaos of Superstorm Sandy

02:00 – Anna’s journey: from theater to tech

06:00 – The making of a generalist

10:00 – Joining Cascade and fixing retention

11:00 – Creating a “working rhythm”

14:00 – Governance vs. red tape

17:00 – The 5 pillars of strategic maturity

19:00 – Turning strategy into execution

24:00 – How Cascade uses AI internally

28:00 – OKRs, KPIs, and strategy frameworks

33:00 – Who owns strategy?

36:00 – Rebuilding a business overnight

43:00 – Closing thoughts

Between Two COO's - https://betweentwocoos.com 

Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascade

Anna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwood

Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514 

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo

Guest: Lance Willett, Chief Quality Officer at Automattic

Topics Covered:

• How Automattic’s open source culture evolved over 20 years
• What a Chief Quality Officer actually does—and why it matters
• Quality = Craft × Context, and how that feedback loop scales
• Automattic’s AI strategy: support bots, contextual UI, and site generation
• The importance of tools like Linear and Storybook in enforcing quality
• How Automattic balances speed, risk, and governance with AI experimentation
• Lessons from stabilizing Tumblr during its post-acquisition reboot
• Prioritization and the dangers of unbounded optimism
• Leadership takeaways from working closely with Matt Mullenweg

00:00 – 03:00: Intro and Lance’s journey from freelancer to Automattic

03:00 – 06:30: How Automattic’s open source ethos evolved over 20 years

06:30 – 10:30: What it means to be a Chief Quality Officer—Craft × Context

10:30 – 15:00: Scaling quality: repo sprawl, signal vs. noise, and auditing

15:00 – 20:00: UX details like forms, performance, and speed as quality levers

20:00 – 24:00: Driving culture change with standard tooling (Linear, Storybook)

24:00 – 28:00: Guardrails for AI experimentation and internal governance

28:00 – 32:00: AI at Automattic: support bots, contextual UI, AI site builder

32:00 – 36:00: Competing with Webflow, Wix, and Squarespace through innovation

36:00 – 38:30: Balancing ecosystem contribution with revenue and investor pressure

38:30 – 41:00: Lessons from stabilizing Tumblr: cost, culture, safety, turnover

41:00 – 44:00: Automattic’s long-term challenge: bounded optimism and focus

44:00 – 46:30: Leadership wisdom from Matt Mullenweg: details always matter

46:30 – 49:00: Lance’s $250K mistake—and what it taught him about leadership

https://brodo.com/ (our other sponsor 😂)

https://fullstackleader.blog/ (work topics: WordPress, tech, productivity, quality, & more)

https://lance.blog/ (fun stuff: poems, stories, links; photos “on the go”)

https://linear.app/

https://clay.earth/ via https://automattic.com/2025/06/12/automattic-welcomes-clay/

Companies with dedicated quality efforts:

https://anthonyhobday.com/blog/20240914.html

> While fixing small bugs might not 10x your growth overnight

> Not fixing them will make 10x growth impossible over time

Credit: Casey Winters – someone you should have on this show if you haven’t already

https://caseyaccidental.com/

Episode webpage - https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpress

Michael Koenig - https://linkedin.com/in/michael-koenig514 

Between Two COO's - https://betweentwocoos.com 

Get 90 days of Fellow's AI meeting assistant at fellow.app/coo

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 to custom GPTs (23:00–26:00)

How Linda builds a culture of innovation — and why bad ideas are worth celebrating (29:00)

Leading through operational ambiguity and defining what to say “no” to (49:00)

How product thinking helps Linda prioritize and run the business (54:00)

Creating an actual in-office “innovation lab” — and what worked (1:04:00)

Wild story: how her team navigated the SVB collapse weekend (1:08:00)

Get 90 days of Fellow's AI meeting assistant at fellow.app/coo

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-agent communication: “Your AI agent will talk to my AI agent—and we’ll both just read the summary.”

Timestamps:

(02:00) Defining agentic AI in customer service

(06:30) From deflection to resolution: Kustomer’s AI in action

(10:15) How AI is changing the org chart and team design

(14:00) The problem with low-context playbooks

(17:45) RevOps structuring and ownership

(22:00) Forecasting: visibility vs. execution

(27:00) AI tooling, integration, and buyer psychology

(31:00) Agent-to-agent interactions and AI futurecasting

(34:30) What Doug’s watching next in ops and AI

Links

Doug Hanna on LinkedIn - https://www.linkedin.com/in/douglashanna1/

Kustomer - https://www.kustomer.com/

Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514

Between Two COO's - https://betweentwocoos.com 

Get 90 days free with Fellow's AI Meeting Assistant - https://fellow.app/coo

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 significantly impact RevOps by improving efficiency, though human judgment remains crucial.

Metrics and KPIs in RevOps must directly correlate to revenue growth, profitability, and organizational efficiency.

Brad emphasizes proactive disruption, transparency, and alignment to navigate the rapid evolution of sales operations.

Timestamps:

(02:00) What is RevOps and how Brad transitioned into it from finance

(07:00) Common misconceptions and early mistakes in RevOps

(11:00) Building a robust RevOps foundation and data hygiene

(15:00) Creating alignment across sales, marketing, and customer success

(20:00) Key metrics and strategic decision-making in RevOps

(24:00) AI’s impact on RevOps and potential pitfalls

(30:00) Real-world experiences with AI-powered sales calls

(33:00) RevOps vs. SalesOps and defining terms clearly

(36:00) Advocating for RevOps budgets and demonstrating value

(40:00) Lessons learned about effective communication and internal alignment

Links:

90 Days Free of Fellow's AI Meeting Assistant: https://fellow.app/coo

Brad Rosen on LinkedIn: https://www.linkedin.com/in/bradrosen1/

Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514/  

Sales Assembly: https://www.salesassembly.com/

Between Two COO's: https://betweentwocoos.com 

Episode URL: https://www.betweentwocoos.com/sales-assembly-president-brad-rosen-on-unlocking-growth-and-why-revops-is-critical-for-sustainable-scaling 

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo

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 utilizing LLMs and managing AI economics.

(36:00) How to build an AI-first company from scratch.

(40:00) Why existing companies struggle to adopt AI effectively.

(44:00) Practical advice on starting AI implementation in established companies.

Key Takeaways:

Fellow transformed from a productivity tool into a strategic, AI-powered assistant helping organizations automate meetings, streamline workflows, and derive actionable insights.

Aydin emphasizes the necessity of disruptive innovation, detailing Fellow’s cultural shift toward agility and fearlessness to stay ahead in the AI-driven landscape.

Security, privacy, and compliance remain core to Fellow, with advanced governance and redaction features designed specifically for internal enterprise meetings.

Real-world AI applications include automatically generating meeting summaries, tracking and following up on action items, updating CRM and project management systems, and creating customized client communications.

Insights on successful AI adoption: Aydin highlights practical steps organizations should take, from establishing AI councils to experimenting actively with new technologies and leveraging external AI consultants.

Links

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo

Episode URL: https://betweentwocoos.com/the-bold-pivot-from-meetings-to-ai-with-aydin-mirzaee-ceo-of-fellow

Between Two COO's website: https://betweentwocoos.com 

Michael Koenig on LinkedIn: https://linkedin.com/in/michael-koenig514

Aydin Mirzaee on LinkedIn: https://www.linkedin.com/in/aydinmirzaee/

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo

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 geopolitical impact of AI regulation. For leaders and operators navigating AI in business, this episode provides crucial insights into managing AI technology within regulatory frameworks.

00:00 Introduction to Fellow and AI Meeting Assistant

01:01 Introduction to Between Two COOs Episode

02:08 What is the EU’s AI Act?

03:42 Prohibited AI Practices in the EU

07:46 Enforcement and Compliance Challenges

12:18 US vs EU: Regulatory Landscape

29:58 Impact on Companies and Consumers

31:55 Future of AI Regulation

Between Two COO's - https://betweentwocoos.com 

Between Two COO's Episode 

Michael Koenig on LinkedIn

Flick Fisher on LinkedIn

Flick on Data Privacy and GDPR on Between Two COO's

More on Flick's take of the EU's AI Act