Field Notes from an AI Operator
We built our organizations for a world where change could be managed toward a destination.
Transform the organization. Implement the system. Adopt the new operating model. Then operate it.
That assumption no longer holds.
In the AI era, there is no fixed destination.
The advantage won't come from perfectly predicting what comes next. It will come from building leaders and organizations capable of continuously learning, adapting, and evolving.
Jerold McDonald
Founder + AI Operating Partner, ethos AI Labs
Builder · Operator · Advisor · Board Director
Perspective
I've spent my career following the work.
I started on the front lines of healthcare and kept following the work: through operations, revenue cycle, technology, building companies, advising leaders and serving in boardrooms.
Today, I’m Founder + AI Operating Partner at ethos AI Labs, where we’re building AI-enabled services and working with organizations on what happens when AI moves beyond the tool and starts taking responsibility for the work.
Each seat has exposed a different part of the same system and, increasingly, the same question:
What has to change for the organization itself to work better?
Operated
Nearly two decades across healthcare operations, revenue cycle, technology and service delivery, beginning on the front lines.
This experience spans complex environments including health systems, medical groups, health plans, services and technology organizations.
Selected organizations + environments
Built
Founder across venture-backed, bootstrapped and nonprofit organizations.
Today, building ethos AI Labs around AI-enabled services, execution ownership and the changing operating model of work.
Previously co-founded Omaiven Health, a venture-backed healthcare AI and automation company.
Founded
Selected company-building ecosystem
Advised
Worked with leaders across healthcare, services, technology and academia on applied AI, operations, organizational design and how new capabilities translate into real operating change.
Board Director
Governance experience spanning health plans, healthcare technology and academia, including Sendero Health Plans, BB Imaging / TeleScan and Trinity University’s Health Care Administration Advisory Council.
Selected board + governance
Much of this work was forged in healthcare, across hospitals and health systems, medical groups and health plans. The thinking and advisory work extends well beyond it.
"Technology should increase human agency."
Field Notes from an AI Operator
Keynotes + topics for speaking engagements
Ideas worth bringing into the room.
Five conversations for leaders navigating what AI changes about work, organizations, leadership and access.
- 01
When AI owns the work
We’ve spent years asking what AI can do. The more important question now is what we’re willing to let it own.
Most organizations still approach AI as something people use: a tool added to a workflow, an assistant given to an employee, or an experiment running alongside the business.
That changes when AI begins taking responsibility for more of the work itself.
Leaders then face a different set of questions. What should AI own? Where are people essential? Who is accountable when execution crosses between the two? And what has to change around the work when execution no longer belongs entirely to humans?
This talk helps audiences see that shift and think more deliberately about how work, responsibility and operating models may need to change.
What to expect
- A clearer way to distinguish using AI from actually changing how work gets done.
- Practical questions for deciding where greater AI ownership makes sense and where it doesn’t.
- A better lens for thinking about the human roles, accountability and operating changes that follow.
- 02
The compounding organization
Your organization generates valuable intelligence every day. How much of it survives tomorrow?
Organizations learn constantly. A customer surprises you. A process fails. Someone finds a better way. A leader makes a judgment call that works.
But much of that learning disappears into meetings, inboxes, chat threads and individual memory. The organization has the experience without necessarily getting smarter because of it.
AI creates an opportunity to change that equation.
This talk explores what becomes possible when organizations get better at capturing what they learn, carrying that learning forward and applying it to the next decision. The advantage is not simply having more information. It is building an organization whose experience compounds.
What to expect
- A new way to recognize the valuable learning organizations routinely generate and lose.
- A clearer distinction between storing information and actually becoming better because of experience.
- Questions leaders can use to examine whether knowledge, judgment and improvement are compounding across their organization.
- 03
Organizational fitness
What are we really optimizing for?
Revenue, margin and EBITDA tell us important things about the organization we’ve built. They tell us much less about whether that organization is fit for what’s coming.
An organization can look successful on paper while becoming harder to change, exhausting the attention of its leaders, operating with little room for disruption, or struggling to turn new capabilities into actual capacity.
In an environment where the destination itself keeps moving, performance today is only part of the equation.
This talk challenges leaders to think beyond efficiency and ask a harder question: are we building an organization with the ability to absorb change, adapt, create room to move and keep getting better?
What to expect
- A broader way to think about organizational performance beyond conventional financial and operating measures.
- A practical lens for spotting where apparent efficiency may be reducing the organization’s ability to respond and adapt.
- Better questions for deciding what capacity, flexibility and leadership attention are actually worth.
- 04
The C-suite challenge
How do you lead when nobody has the map?
Executives are being asked to move faster on AI while the technology, risks and rules keep changing underneath them.
Move too slowly and you may miss an important shift. Move recklessly and the consequences can be just as serious.
Meanwhile, leaders are expected to develop an AI strategy, evaluate investments, protect the organization, prepare their workforce and somehow determine whether everyone else is already ahead.
The answer is not for every executive to become an AI expert.
This talk focuses on the leadership challenge underneath the technology: how to ask better questions, establish useful boundaries, create permission to learn and lead an organization through a transition whose endpoint nobody can confidently describe.
What to expect
- Greater clarity about what leaders actually need to understand about AI and what they don’t.
- A way to separate competitive urgency from the pressure to chase every new development.
- Practical questions leaders can use with their teams, boards and technology partners to make better decisions under uncertainty.
- 05
Rethinking access
Access is bigger than an appointment.
Healthcare has traditionally measured access through familiar constraints: appointments, clinicians, facilities, hours and geography.
Those things still matter. But they describe the system we built, not necessarily the limits of what access can become.
Many of the barriers patients experience occur before, between and around clinical encounters: finding the right entry point, completing administrative work, navigating requirements, getting answers and staying connected to care.
This talk asks audiences to reconsider what healthcare access means when technology and new operating models allow us to redesign more of the journey around the person seeking care rather than the limitations of the existing system.
What to expect
- A broader definition of healthcare access that extends beyond appointment availability.
- A clearer view of the operational barriers that shape whether people can actually receive and navigate care.
- New questions for imagining how technology, operations and redesigned work can expand access without losing the human experience.
"The goal isn't more information. It's a different way to see the problem, imagine what's possible, and plot a better path forward."
Beyond the keynote
Some conversations need a smaller room.
Field Notes: C-Suite Circles
The questions leaders most need to ask aren't always the ones they want to ask from a stage, in a board meeting or in front of their teams.
C-Suite Circles create room for the questions underneath the strategy: what you understand, what you don't, where the organization is actually behind, what deserves urgency and what can wait.
Bring Jerold into the conversation- Are we actually behind?
- Have we adopted AI, or just bought access to it?
- How much should I personally understand?
- How do I know whether the person I've delegated this to actually knows what they're doing?
- How fast is too fast?
- How do we experiment without unnecessarily exposing the organization?
Track record
The questions change. The work continues.
Nearly two decades across the front lines, operations, technology, company building and boardrooms have changed the questions. The work has always been about understanding what comes next and making it useful now.
Service. Stewardship. Agency.
I grew up in a multigenerational military family where service was never an abstract idea. I found my own path to it through building organizations and businesses.
Technology has always interested me for the same reason: what becomes possible when we give people more capacity, more choices and more agency?