Kyle Littlejohn
Chief of Staff · Strategy & Operations Leader · Cross-Functional Execution · AI-Augmented Decision Support
+1 (540) 604-3405 · khlittlejohn@gmail.com ·
kylelittlejohn.com · New York, NY
Summary
Chief of Staff and Strategy & Operations leader with 12+ years as the operator Senior Leaders hand their hardest cross-functional mandates to, building the planning rhythm, executive reporting, and decision infrastructure that let C-suite leadership move faster across Media & Entertainment, SaaS, Biotech, Financial Services, and Healthcare.
Grew the AMC Networks account from $280K to $2.1M by expanding scope across renewal cycles while running the 16-business-unit operating cadence that took ~30% out of execution cycle time. Partnered directly with Kaseya's C-suite through its $350M to $1.75B scale, building the KPI and board-reporting infrastructure that integrated 14 acquisitions. Also designed and runs a production system of 100+ specialized AI agents, with a human approval gate on everything that leaves it.
Key Achievements
C-Suite Partnership & Enterprise Scale
Partnered directly with Kaseya's C-suite through a $350M to $1.75B scale, owning the planning rhythms, KPI infrastructure, and board / QBR / Steering Committee reporting that kept a $1B+ organization aligned.
Cross-Functional Execution Without Authority
Aligned 16 business units and 12 external partners at AMC Networks against shared priorities, building the governance and operating cadence that cut execution cycle time ~30%.
Strategic Initiative Ownership
Directed multiple transformation initiatives at bluebird bio spanning Procurement, Legal, HR, and Operations, turning cross-functional process reviews into $1M+ in annualized savings.
AI-Augmented Executive Operations
Built AI-assisted reporting and briefing workflows in Claude, ChatGPT, and Copilot that cut executive-prep time and turned status into decision-ready leadership updates.
Experience
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, owning strategic execution, executive operations, and cross-functional delivery across the FAST & AVOD organization.
- Coordinated 16 business units and 12 external partners across Product, Marketing, Distribution, Technology, and Operations, running the operating cadence that kept leadership decisions moving without direct authority over any team.
- Built the governance frameworks and review rhythms across 32 digital channels (News, Sports, Reality TV, Scripted) that cut execution cycle time ~30%, giving Executives a single view of status, risk, and decisions.
- Authored executive briefings, board-style updates, and pre-meeting materials that let senior leadership walk into every key decision informed and with a clear point of view.
- Stood up AI-assisted reporting and briefing workflows using ChatGPT and Microsoft Copilot, compressing executive-prep time and converting raw status into decision-ready leadership updates.
- Drove the AMC+ launch in direct partnership with platform leadership, coordinating delivery across Product, Engineering, QA, and Marketing and contributing to 65% digital revenue growth.
- Bridged product roadmap, engineering delivery, and go-to-market into a single execution plan, so cross-functional teams stayed pointed at the same outcomes.
- Surfaced launch risks and dependency conflicts early to senior leadership, turning what would have been escalations into pre-decided trade-offs.
- Synthesized status across multiple workstreams into one executive narrative, replacing fragmented stand-ups with a single weekly read for the leadership team.
- Served as the strategic liaison between SOL Consulting leadership and AMC Networks Executives, aligning enterprise priorities, delivery strategy, and operational execution across a multi-year engagement.
- Grew the AMC Networks engagement from $280K to $2.1M annually by partnering with senior client stakeholders to identify priorities, shape scope, and sustain executive trust across multiple cycles.
- Set the operating cadence and accountability rhythm for a team of 8 consultants, holding delivery to client expectations and reporting performance back into both leadership teams.
- Brokered escalations between Client Executives and delivery leadership, turning friction points into agreed paths forward and protecting the engagement from cycle to cycle.
Partnered with C-suite leadership through Kaseya's rapid growth from $350M to $1.75B, owning the financial planning, operational execution, and cross-functional alignment that kept a $1B+ SaaS organization moving in the same direction.
- Built the post-close operating system that brought 14 acquired companies onto one set of plans, reporting, and metrics, giving leadership a single view of a fast-consolidating portfolio.
- Monitored performance across $1B+ in revenue alongside C-suite and Executive Leadership, advising on investment and acquisition decisions and keeping spend tied to strategic targets.
- Prepared executive and board-level reporting for QBRs and Steering Committee meetings, turning performance, risks, and recommendations into the narrative leadership used to set portfolio priorities.
- Built KPI dashboards and reporting frameworks that gave leadership real-time visibility across business units, replacing manual status-chasing with a single source of truth in executive reviews.
Consulting Manager. Partnered with Executive Stakeholders at a biotech client to lead operational transformation and cost optimization, turning cross-functional process reviews into measurable financial outcomes.
- Directed multiple transformation initiatives across Procurement, Legal, HR, and Operations at bluebird bio, delivering $1M+ in annualized savings for the Executive Sponsor.
- Led cross-functional contract reviews with Finance, Legal, HR, and Operations, negotiating improved vendor terms and consolidating spend categories on behalf of Executive Stakeholders.
- Built the reporting framework that tracked initiative progress, financial impact, and program risks, giving Executive Stakeholders one view of the transformation portfolio.
- Synthesized weekly initiative progress into executive narratives for the bluebird leadership team, sharpening the C-suite's view of cost-savings risk and trade-offs.
Senior Consultant / Consultant. Delivered enterprise transformation engagements across Financial Services and Healthcare, focused on execution, governance, and the operational infrastructure clients needed to sustain improvement.
- Partnered with stakeholders on a next-generation internal credit rating platform, translating business needs into functional specifications and feeding development priorities back to leadership.
- Drove process optimization and performance tracking across the SDLC, contributing to 20% efficiency gains for the program.
- Led implementation of a small-business health insurance product within a 7-project program, coordinating cross-functional teams against strict regulatory timelines.
- Tracked progress, risks, and dependencies into executive-ready status, keeping business and operational stakeholders aligned through launch.
Systems Analyst Intern. Supported enterprise technology delivery by bridging business and technical teams within government technology programs.
- Translated business and operational requirements into technical specifications for development teams supporting NY State enterprise software delivery.
Education
College of William & Mary Williamsburg, VA
B.S. Neuroscience · Minor in Process Management & Consulting
Certifications · Professional Scrum Master I (PSM I) · Google Project Management Certificate · Generative AI for Project Managers · AI Foundations for Business Professionals