Tim Jessberger / Digital Growth, Platform Architecture & AI Operations

Better teams, tighter systems, smarter tools.

Sr. Director of Web & Platform · McGraw Hill

I lead digital growth, web platform architecture, and AI-enabled operations. At McGraw Hill, I build the teams, custom internal tooling, and deterministic AI workflows that power a national PreK-12 digital ecosystem.

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Commercial strategy
meets technical execution.

Over more than a decade at McGraw Hill, I have grown from a channel specialist into a Senior Director responsible for the strategy and technical foundation of a national PreK-12 digital ecosystem.

After spending years running high-conversion marketing (SEO, AEO, CRO, B2B lead gen), I moved deep into platform engineering concepts like APIs, microservices, and custom internal tooling. Today, I scale team output through better teams, tighter systems, and smarter tools. By equipping teams with deterministic, auditable agentic workflows and modern web architecture, I help organizations shift from manual digital tasks to high-velocity, product-led growth.

Operational Foundation

Growth & Commercial Strategy

SEO, AEO & Generative Discovery (GEO/LLMO)
Conversion Rate Optimization (CRO)
B2B Lead Generation & Demand Gen
Product-Led Growth (PLG) & Onboarding
B2B eCommerce Frameworks

Platform & AI Engineering

Deterministic, Auditable Agentic Workflows
Custom Internal Tooling & Automation
Web Platform Architecture & Microservices
API Development & System Integration
Product Telemetry (Adobe Analytics & Pendo)

Core Expertise

The strategy.
The systems behind it.

Scaling enterprise output requires more than good ideas. It takes disciplined processes, adaptable teams, and production-grade technology.

Operational Scale (Process)

Rebuilding legacy digital operations into high-output growth engines using deterministic, auditable agentic workflows, standardized playbooks, and streamlined go-to-market execution.

AI & Platform Innovation (Technology)

Building custom internal tooling and deploying practical AI systems, generative discovery strategies (GEO/LLMO), and product telemetry (Adobe/Pendo) to cut customer friction and speed up delivery.

Cross-Functional Leadership (People)

Translating executive business goals into clear engineering and marketing execution. I build teams where marketers think like technologists and builders understand commercial impact.

Enterprise Growth Strategy

Architecting B2B digital ecosystems and automated onboarding workflows that drive adoption, retention, and national market share.

AI & Decision Systems

From Frontier Models
to Production Systems.

I turn AI from an individual productivity experiment into a governed, repeatable capability across technical execution and executive decision-making.

01 · Deterministic Workflows

Make It Auditable

Design multi-step agentic workflows with strict validation gates, structured schemas, and human-in-the-loop checkpoints so teams can trust and audit every output at scale.

02 · Custom Internal Tooling

Build the Multipliers

Develop specialized browser extensions, debugging utilities, and internal web apps that eliminate repetitive engineering and marketing bottlenecks across the enterprise.

03 · Decision & Market Intelligence

Clarify the Tradeoffs

Synthesize fragmented market signals and business context into structured analytical frameworks that leaders can examine, challenge, and act on.

Anonymized Enterprise Work

Decision & Execution
Architecture

† Details protected by NDA

I lead internal AI initiatives that pair frontier models with strict validation controls.

Business Question / Analytical Framework / AI Workflow / Human Validation / Executive Decision

My work spans custom internal tooling, deterministic model workflows, and analytical frameworks that turn complex data into auditable outputs teams and executives can act on.

Leadership