Between Two COO's with Michael Koenig

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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.

 

Topics Covered

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.

 

AI, Security, and Synthetic Identities

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.

 

Key Takeaway

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
What we cover
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
Episode Chapters / Timestamps
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