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Strategy & Operations · Chief of Staff · AI Transformation

Senior leaders hand me the mandate nobody owns.

I turn executive priorities into operating cadence, cross-functional execution and measurable results, across SaaS, media, biotech, financial services and healthcare. Now I build those systems with AI.

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Based
New York · Remote
Currently
Founder, KLJ Ventures · AI systems consultancy

Career

Six roles. Five industries. One operating method.

  1. Summer 2013

    Maximus

    Systems Analyst Intern
    There to solve

    Business and operational requirements on New York State government technology programs needed translating into specifications developers could build from.

    Owned

    The translation itself, under the guidance of senior systems analysts. Nothing independently.

    What it was

    Learning the work. No operating method yet, and the record does not pretend otherwise.

  2. 2014–2017

    Optimity Advisors

    Consultant → Senior Consultant
    There to solve

    Enterprise transformation and regulatory compliance across financial services, healthcare and media. At Beacon Health, a company-wide reorganization to cut costs and use staff time better.

    Owned

    The diagnostic interviews with client-facing and clinical provider teams, and the financial models and executive presentations behind the reorganization. Leadership approved and ran it.

    Evidence

    The Beacon Health engagement cut operating costs 15% and improved process efficiency 25% over six months.

    Move developed

    Find the layer. The only work in the record that begins by interviewing the organization to locate the real problem rather than accepting the presented one.

  3. 2017–2018

    AArete

    Consulting Manager
    There to solve

    bluebird bio needed to reduce cost without degrading the service levels the business depended on.

    Owned

    Vendor renegotiation and purchasing redesign across procurement, legal, HR and operations, and the reporting framework that put initiative progress, financial impact and risk in one place.

    Evidence

    $1M+ in annualised savings, with every service commitment preserved. I was the consultant on the engagement, not a bluebird bio employee.

    Move developed

    One basis for comparison. Cost structure and existing service commitments assessed together, rather than cutting first and checking commitments after.

  4. 2018–2020

    Kaseya

    Senior Manager, Strategic Finance & Business Operations
    There to solve

    Fourteen acquisitions had each arrived with their own systems, KPI definitions and planning calendars. Leadership could not compare anything to anything, which is a capital allocation problem wearing a reporting problem's clothes.

    Owned

    The post-close operating and reporting infrastructure, and the analysis underneath board-level reporting. I did not own the acquisition decisions.

    Evidence

    Fourteen companies onto one reporting stack instead of fourteen. I contributed the financial narrative and data room materials behind a $500M+ round from TPG and Insight Partners. The company's valuation moved from roughly $350M to $1.75B over the period.

    Move proven at scale

    One basis for comparison. Leadership needed a common basis for comparison, which is a different thing from more visibility and has to be built deliberately underneath the businesses.

  5. 2020–2026

    SOL Consulting

    Director, Strategy & Client Delivery
    There to solve

    A fast-growing streaming portfolio at AMC Networks running on processes built for something smaller. Teams spent their time reconciling information instead of moving campaigns forward.

    Owned

    The account and the operating cadence throughout, and a delivery team of 8 whom I managed directly. No authority over any of the 16 business units whose work had to change.

    Evidence

    End-to-end campaign cycle time fell roughly 30%. The client expanded the engagement from $280K to $2.1M across five years.

    Move developed

    Establish cadence. Reporting and rhythm are operating infrastructure rather than administration. Installing them early is what makes risk visible while leadership still has cheap options.

  6. 2026–Present

    KLJ Ventures

    Founder, AI Systems Consultant
    There to solve

    A consultancy needing more throughput than one person has, without putting my name on work nobody had checked.

    Owned

    Every design decision, failure diagnosis and governance rule in the system.

    Evidence

    120+ specialized agents across 14 functional domains, with automated checks enforced on everything the careers pipeline produces before it reaches my review.

    What AI added

    Nothing grades its own work. The principle is longstanding. The explicit, automated mechanism is new, because a colleague brings some independent judgment to a review and a language model brings none.

Evidence

Selected work

Three environments, one method, different evidence.

Kaseya

2018–2020

Portfolio-scale operating infrastructure

Mandate
Fourteen acquisitions, each reporting on its own systems and definitions. Leadership could not compare anything to anything.
Intervention
Built the post-close operating and reporting infrastructure, and standardized KPI definitions across the portfolio.
Result
14 companies onto one reporting stack. $500M+ growth financing from TPG and Insight Partners, where I contributed the financial narrative and data room materials. Valuation moved from roughly $350M to $1.75B across the period.
Why it matters
Leadership declined an acquisition on the analysis I built. Infrastructure that never changes a decision has failed.
Read the case study →

AMC Networks

2020–2026

Enterprise transformation without authority

Mandate
A streaming portfolio growing faster than the operating model underneath it, across 16 business units, 12 partners and 32 channels. None of them reported to me.
Intervention
One source of truth for status, risk and decisions, a standardized cadence across every unit and partner, and early risk escalation.
Result
Campaign cycle time fell roughly 30%. The client expanded the engagement from $280K to $2.1M. Digital revenue grew about 65% across streaming and distribution; I ran the AMC+ launch delivery that contributed to it, and the growth was a company result rather than mine alone.
Why it matters
Alignment came from visibility, not mandate. That is the whole argument for building the cadence early.
Read the case study →

Executive Office

2026–Present

An AI operating system built and governed from scratch

Mandate
Produce work I would sign my name to, repeatedly, without reading every word myself. Generating output was never the hard part.
Intervention
Separated generation from evaluation so no agent grades its own work, and encoded each failure as an automated check rather than fixing it once.
Result
120+ specialized agents across 14 functional domains, with automated checks enforced on everything the careers pipeline produces before it reaches my review.
Why it matters
The system caught itself inventing a number inside a paragraph claiming it prevents invented numbers. That is the check working.
Read the case study →
The method

Decision infrastructure

I have entered five industries cold and spent most of my career outside the organization I was trying to move. The method is what is left when you cannot rely on knowing the domain or directing anyone.

Five moves. They depend on one another rather than happening in order, and the last one is the only test that counts.

  1. Find the layer

    Integrate the layer, not the company.

    The presented problem and the real problem are usually different. Fourteen incompatible KPI definitions is a symptom; a capital allocation problem is the cause.

  2. One basis for comparison

    The decision requires a common basis for comparison.

    Not more visibility, which is a different thing and does not produce it. You cannot allocate capital across a portfolio you cannot compare.

  3. Establish cadence

    Cadence earns its authority.

    Reporting and rhythm are operating infrastructure, not administration. Installed early, they make risk visible while leadership still has cheap options.

  4. Nothing grades its own work

    Inspection should be cheap.

    A system that evaluates its own reasoning is exposed to the assumptions that produced the error. The principle is longstanding; the automated mechanism is new, and the AI work is what forced it.

  5. Reach the decision

    The real test is whether leadership does something different because of the infrastructure.

    Not whether it produces reports. At Kaseya the clearest proof was an acquisition the executive team declined on analysis I built. I did not make that call, and it was not mine to make.

Around all five

Every failure becomes a permanent check.

A correction that lives in a document gets forgotten. One that lives in a gate does not. Applied to machine-produced work, the same rule reads: fabrication is a system bug.

Expertise

Core capabilities

Operating toolkit
  • AI Claude Code · ChatGPT · Copilot · Gemini
  • Data & planning SQL · Tableau · Looker · Excel · NetSuite · Adaptive Planning
  • Delivery Jira · Confluence · Smartsheet · Microsoft Project
Background

The operator, the builder, and the person

Kyle Littlejohn
The operator

Five industries I entered without the domain: biotech, credit ratings, health insurance, infrastructure SaaS and streaming media. Becoming useful quickly turns out to be most of the job when you are the person handed the thing nobody owns. That pattern is not on my resume as a skill, and it is probably the most transferable thing I do.

The builder

I studied neuroscience at William & Mary with a minor in process management, which sounded like an odd pairing at the time. Both are the study of how a system takes in incomplete information and produces a decision. I would rather build the operating model than inherit one, which is eventually why I started building the systems instead of advising on them.

The person

Thirty-plus endurance races, marathons and Hyrox mostly, with the occasional ultra when I have lost perspective. Training is the one part of my life with a genuinely honest feedback loop, which is probably why I keep going back to it. Outside the work I spend an unreasonable amount of time running, traveling and figuring out how to make things work better than they did the first time.

Full background →

12+years operating
5industries entered cold

Let's talk.

A 20-minute call is the fastest way to find out whether I am useful to you.

Open to select executive opportunities.

Or email me directly at khlittlejohn@gmail.com.