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In this episode, Michael Koenig speaks with Greg Keller, co-founder and CTO of JumpCloud, about identity access management and why it’s becoming one of the most important operational systems in the age of AI.

Greg explains how traditional identity systems were designed for office-based companies running Microsoft infrastructure and why that model broke as companies moved to SaaS, cloud infrastructure, and remote work.

The discussion then turns to the next big shift: the rise of AI agents and synthetic identities inside organizations.

As companies deploy more AI tools, the number of machine identities may soon outnumber human employees. Managing what those systems can access will become a critical security and operational challenge.

What a CTO actually does

Greg explains the different types of CTO roles and how technology leaders help companies anticipate where the market is headed.

Identity Access Management explained simply

IAM answers three core questions inside every company:

Who are you?

What can you access?

How is that access managed?

Why the old IT model broke

Traditional identity systems were built for on-premise offices and Microsoft infrastructure. Modern companies now operate across:

SaaS applications

cloud infrastructure

remote work environments

multiple operating systems

How JumpCloud approaches identity

JumpCloud was built to manage identity across devices, applications, and infrastructure regardless of platform.

Where Okta fits in the ecosystem

Okta helped modernize browser-based authentication through Single Sign-On, while JumpCloud focuses on broader identity infrastructure.

Why COOs should push AI adoption

Greg argues AI adoption is no longer optional. Companies must encourage teams to improve productivity and efficiency using AI.

The rise of synthetic identities

AI agents, bots, APIs, and service accounts are becoming new actors inside companies that require identity governance.

Bots may soon outnumber employees

Organizations will soon manage more machine identities than human ones.

AI as a potential insider threat

AI systems can become security risks if they are granted excessive permissions or misinterpret policies.

The API key governance problem

Many AI integrations rely on API keys, which are often poorly managed and can create hidden security risks.

As companies adopt AI, identity access management becomes the control layer that determines what both humans and machines are allowed to do inside the organization.
The companies that manage identity well will move faster and operate more securely.

Links:

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

Greg on LinkedIn: https://www.linkedin.com/in/gregorykeller/

JumpCloud: https://jumpcloud.com/

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

Episode Link: https://betweentwocoos.com/ai-agents-identity-access-greg-keller

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Guest: Seth Levine

Book: Capital Evolution

Podcast: Between Two COOs

Host: Michael Koenig

• Why Seth wrote Capital Evolution and why now
• Why today’s economic shift is structural, not cyclical
• How power has moved from public institutions to businesses
• What companies are being asked to carry that they weren’t built for
• How AI fits into this broader realignment
• Early signals that companies are adapting well to AI
• What strong executive teams do differently during uncertainty
• Common leadership traps when change happens too fast
• A real crisis from a portfolio company and what the executive team did well
• The new leadership muscle operators need for the next decade

00:00 – Introduction

01:40 – Seth’s 30-second pitch for Capital Evolution

04:05 – Why this shift is structural, not cyclical

07:20 – What’s broken in the current economic model

11:00 – The power shift from government to business

15:10 – What leaders are quietly losing

18:45 – Where AI fits into this realignment

23:30 – What boards see when AI adoption works

28:05 – How strong executive teams handle uncertainty

33:40 – Leadership traps during rapid change

38:10 – A crisis inside a portfolio company

44:00 – The new muscle operators must build

48:50 – A moment Seth never thought he’d see

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

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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

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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 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)