The operating layer between strategy and execution

Chief of Staff & Strategy / Operations Leader · 12+ Years

Kyle Littlejohn

I turn ambiguous mandates into measured results, and I built a production AI operating system that multiplies how fast that happens.

Career Snapshot

Experience 12+ years as an operator beside Founders, Creators, and the C-suite
Open to Strategy & Operations · Chief of Staff · Program & Project Management · Transformation · Management Consulting
Industries Healthcare · Media & Entertainment · Biotech · SaaS · Financial Services
Based New York · Remote · open to Sydney & London

Why Work With Me

Handed the hard problemsFounders and C-suite Leaders give me the initiative no one else owns, the ambiguous mandate with no clear owner and no roadmap. I set the cadence, align people who don't report to me, and turn it into a plan the organization can actually execute.
AI-native, and provenI designed and run a production AI operating system: 100+ specialists across 12 departments, with a human approving every decision that leaves it. I can build the system and then brief the board on it.
Specific, real outcomesKept a SaaS organization aligned through a $350M to $1.75B valuation, grew an account from $280K to $2.1M, and cut execution cycles by roughly 30% without direct authority. The record below documents each.

Operating experience across

Healthcare, Media and Entertainment, Biotech, SaaS, and Financial Services.

Engagement Highlights

Selected highlights from the work, and the number each one produced.

Kaseya · Senior Manager, Strategic Finance & Business Operations · 2018–2020
The operating and KPI spine of a $1.75B organization
$350M → $1.75B valuation growth through 14 acquisitions and strategic expansion, integrated into the financial planning, KPI infrastructure, and board reporting I owned

Partnered with the C-suite through Kaseya's scale, owning financial planning, KPI infrastructure, scenario modeling, and capital-allocation analysis. Built the Tableau, SQL, and board reporting that leadership used to set portfolio and acquisition priorities.

SOL Consulting · Director, Strategy & Client Delivery · 2020–2026
AMC Networks Enterprise Transformation

Led a single 5+ year engagement spanning 3 concurrent leadership workstreams.

Account Manager
An account grown 7.5x, and the team behind it
$280K → $2.1M annual account growth by expanding scope across renewal cycles, with a team of 8 consultants

Owned the AMC Networks engagement as the operating liaison between SOL Consulting leadership and AMC Executives, the day-to-day relationship the account's growth depended on. Read priorities, shaped scope, and sustained executive trust across renewal cycles while setting the cadence and accountability rhythm for a team of 8.

Senior Program Manager
The operating cadence across 16 business units
~30% faster execution cycles, with no direct authority

Ran the operating cadence and governance across the FAST and AVOD portfolio: 16 business units, 12 external partners, and 32 digital channels. Stood up a single source of truth for status, risk, and decisions, and prepared the executive and Steering Committee materials behind it.

Senior Technical PM
The AMC+ launch and identity feature
~65% growth in digital revenue, with the AMC+ launch a key driver

Led the digital transformation behind the AMC+ subscription launch across Product, Engineering, QA, and Marketing, and built out the AMC+ identity feature for both the launch and the ongoing website enhancements. Turned roadmap, engineering delivery, and go-to-market into one trackable plan, surfacing launch risks and dependency conflicts early.

AArete · Consulting Manager · 2017–2018
Cost transformation, quality held
$1M+ in annualized savings, SLA quality preserved

Directed an operational transformation for gene-therapy company bluebird bio across Procurement, Legal, HR, and Operations. Ran 5 initiatives spanning scoping, renegotiation, and redesign, delivering over $1M in annualized savings with service levels fully preserved.

Optimity Advisors · Senior Consultant · 2014–2017
A next-gen credit-rating platform at Moody's
20% program efficiency gains through SDLC optimization

As the technical business analyst on Optimity Advisors' Moody's engagement, translated business needs into functional specs for a next-generation internal credit-rating platform, and drove the process optimization behind a 20% efficiency gain across the program.

Career Arc

More than a decade of work, from advising enterprise and consulting clients across industries to partnering directly with the C-suite of a $1.75B organization, building the operating systems, KPI infrastructure, and cross-functional programs that turn ambiguous mandates into measurable results.

  1. SOL Consulting Director, Strategy & Client Delivery

    2020–2026

    Served as Account Manager for over five years on the AMC Networks engagement, while progressing through increasingly senior delivery leadership responsibilities, advancing from Senior Technical Project Manager to Senior Program Manager. Grew the account from $280K to $2.1M, ran the operating cadence across 16 business units, and cut execution cycle time by roughly 30%.

  2. Kaseya Senior Manager, Strategic Finance & Business Operations

    2018–2020

    Partnered directly with the C-suite through the scale from a $350M to a $1.75B valuation, owning the financial planning, KPI infrastructure, and board reporting that integrated 14 acquisitions.

  3. AArete Consulting Manager

    2017–2018

    Led an operational and cost transformation for gene-therapy company bluebird bio, delivering over $1M in annualized savings with service levels fully preserved.

  4. Optimity Advisors Consultant → Senior Consultant

    2014–2017

    Drove enterprise transformation across Financial Services, Media & Entertainment, and Healthcare, from a next-gen credit-rating platform at Moody's (20% efficiency gains) to a compliance-critical health-insurance product launch at CareFirst.

  5. Maximus Systems Analyst Intern

    Summer 2013

    Bridged business and technical teams on a government technology program, translating requirements into specs for enterprise software delivery.

  6. Education

    College of William & Mary Williamsburg, VA

    B.S. Neuroscience · Minor in Process Management & Consulting

    2010–2014

What I'm Looking For

I know exactly what I'm best at: the hard, cross-functional problem a Senior Leader needs owned end to end. I'm looking for the role where that is the whole job, and these 5 fit cleanly.

Chief of Staff

I translate executive priorities into operating systems, decisions, and accountability. I run the operating cadence and OKRs, prepare the board and QBR materials, and drive the cross-functional initiatives no one else owns. Done in direct partnership with the C-suite of a $1.75B organization.

Strategy & Operations

I connect strategy, financial modeling, operating metrics, and execution. I build the scenario and capital-allocation models behind the decision, stand up the KPI infrastructure, and hold teams to the targets. Hands-on in SQL, Tableau, and Looker, not just the deck.

Program & Project Management

From executive mandate through measurable business outcome. I run complex cross-functional programs end to end, with integrated plans, governance, and dependency and risk tracking. Proven across 14 acquisitions at Kaseya and a 16-business-unit portfolio at AMC Networks.

Management Consulting

I operate as the bridge between executive strategy and frontline execution. I frame the problem, align the sponsors, and run the multi-year engagement that turns a client mandate into measurable outcomes. Grew the AMC Networks account from $280K to $2.1M and led a biotech transformation to $1M+ in savings.

AI Specialist

The operator who builds AI into the operation, not just talks about it. I designed and run a production system of 100+ specialists across 12 departments, with a human approving every decision that leaves it, proof I can lead AI adoption and governance, not just use the tools.

See the system below →

If one of these maps to a problem on your desk, I want to hear about it. The contact form below reaches me directly, and I reply within a day.

Start a conversation →

Skills & Tools

The capabilities I lead with, and the tools behind them. Full detail on every role is in my resume.

Strategy & Operations
Operating model & cadencePMO & governanceKPI / OKR infrastructureScenario & capital-allocation modelingCorporate & business strategyStrategic planningMarket & competitive analysisTransformation & change managementAI strategy, adoption & enablementBoard & executive reportingExecutive decision supportCross-functional leadershipOperating rhythm designLeadership team alignment
Executive Leadership & Business Operations
Executive stakeholder managementFounder / C-suite partnershipStrategic initiative ownershipBusiness reviews & QBRsOrganizational alignmentLeadership communicationsEnterprise prioritizationExecutive reportingCross-functional execution
Data, Analytics & BI
TableauSQLLookerExcelAdaptive PlanningNetSuiteFinancial modelingP&L managementRevenue analyticsForecastingBusiness-intelligence dashboards
AI & Emerging Technology
ClaudeChatGPTMicrosoft CopilotGoogle GeminiAgentic workflowsAI workflow designAI operating modelsAI adoption strategyAI governance frameworksHuman-in-the-loop workflowsAgent orchestrationLLM workflow optimization
Project & Delivery
JIRAMicrosoft ProjectSmartsheetAirtableScrum (PSM I)Portfolio managementDependency managementRisk managementEnterprise delivery governanceAgile transformation

Certifications

Formal credentials behind the skills above.

Professional Scrum Master I
Google Project Management
Generative AI for Project Managers
AI Foundations for Business

AI Expertise & Examples

I built this for other companies. So naturally, I built my own Executive Office.

AI, Put to Work Inside Real Operations

I bring AI directly into the operating work, rather than only the conversation around it. At AMC Networks, I built AI-assisted reporting that turned raw status into decision-ready narratives. Beyond that, I designed and personally run a production operating system on Claude, day to day, that manages my own strategy, operations, and reporting, with 100+ specialists across 12 departments, a 14-stage quality pipeline, and a human on every decision that leaves it.

12departments
100+specialists
14-stageQC pipeline

The Executive Office, by Team

Explore how it's organized: hover or tap a department below to see what it does.

Hover or tap a department

Examples of my AI work

The same systems thinking, documented openly. These cards load live from GitHub.

@khlittlejohn-hue
@khlittlejohn-huebuilding in public on GitHub ↗
3public repos
Claude Codeflagship built with

Live from the GitHub API · no tracking · falls back gracefully if GitHub is unreachable.

Explore my GitHub ↗

Outside the Office

What I do when I'm not running someone's operating cadence.

Endurance Athlete

An endurance athlete across Hyrox, road marathons, and ultras, with 30+ races completed and more on the calendar.

Featured on OutSports
Travel Fanatic

50+ countries and counting, with a disciplined approach to making the most of limited time away from work.

Featured in Condé Nast Traveler ↗
Foodie

A dedicated home cook, continually exploring new cuisines and techniques.

Featured on Food Network

Contact

Hiring for one of my lanes, or staring down a problem that sounds like the ones above? Write me. I reply within a day.

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