AI Transformation Lead

Job Summary

The Enterprise Transformation Manager owns the long-term adoption narrative, strategic workstreams, and technical deployment execution across a dedicated account portfolio. Core daily duties include breaking down ambiguous enterprise operational bottlenecks from first principles, co-designing automated workflows alongside Forward Deployed Engineers, leading senior stakeholder change management sessions, prototyping within the core Pencil platform, and codifying successful turnarounds into institutional "Transformation Blueprints."

Foundational Experience & Strategic Prerequisites

• Professional Implementation Tenure: Minimum of 5+ years of verifiable experience across management consulting, in-house business transformation, complex program management, or enterprise technology implementation—with heavy exposure to technical delivery, digital strategy, and business operations.
• Quantitative Academic Foundation: A strong academic record in a highly quantitative or analytical discipline—such as STEM (Science, Technology, Engineering, Math), Economics, Engineering, or Business—that trained you to dissect complex problems and defend your reasoning under cross-examination.
• AI-Native Professional Habits: Fully AI-native in your day-to-day operations. You actively leverage advanced large language model environments (e.g., Claude Cowork) to optimize your personal output, with hands-on experience utilizing agentic systems (e.g., Claude Code) or related multi-tool command automation frameworks considered a major competitive advantage.
• Technical Literacy & Platform Agility: Deeply comfortable working inside technical environments. You are ready to dive directly into the Pencil platform to configure agents, run system stress tests, and actively hold your own in detailed architectural discussions with a client’s internal engineering team regarding their data stack. Lightweight technical skills—such as writing SQL queries, scripting, or comfortably reading and auditing codebase files—are highly desirable.
• Senior Stakeholder Command: Exceptional communication skills and executive presence. You must possess the confidence to single-handedly lead high-stakes corporate alignment meetings, deliver direct, unfiltered operational feedback to client leadership, and maintain absolute professional composure when scopes shift rapidly.
• Execution History: A documented, highly consistent track record of navigating cross-functional, highly ambiguous enterprise initiatives to successful completion within strict deadlines.

Cultural Alignment & Traits

• Provocative & Brave: Unafraid to respectfully challenge a client’s legacy operating structures, outdated creative approval steps, or protective departmental silos if it protects the long-term success of the deployment.
• Trusted Ally to Change: Comfortable operating within highly fluid, ambiguous, and rapidly changing business conditions, taking personal pride in serving as a grounded, steady partner who guides non-technical users through unfamiliar technical territory.
• Obsession with Embedded Value: Highly focused on driving concrete software adoption, possessing a deep irritation with superficial "innovation theater" or isolated pilots that fail to deliver measurable operational ROI.

Key Responsibilities

1. Strategic Implementation Leadership & Architecture

• Establish the foundational transformation thesis, narrative structure, and long-term rollout blueprint for a defined set of high-value enterprise customer accounts.
• Take highly ambiguous client creative bottlenecks and systematically break them apart from first principles into clear hypotheses, modular workstreams, and sequenced technical decisions.
• Partner cross-functionally with Pencil’s internal Forward Deployed Engineers and Creative Leads to design, stress-test, and deploy specific technical recommendations, system custom-configurations, and implementation timelines.

2. Change Management Leadership & Scaling Governance

• Lead enterprise clients safely through complex corporate transformations, systematically steering them away from siloed tool pilots and into deeply integrated, AI-driven creative workflows.
• Navigate highly complex corporate stakeholder landscapes, accurately mapping out operational blockers, identifying internal product champions, and engineering the executive buy-in required for organizational adoption.
• Translate highly abstract Generative AI functionalities into exceptionally clear, highly repeatable operating procedures (SOPs) that client creative and marketing teams can execute confidently in their day-to-day routines.

3. Continuous Product Feedback Loops & Playbook Codification

• Actively serve as the definitive internal voice of the customer, capturing and organizing systemic product friction points, feature gaps, or critical errors to deliver direct, actionable insights to our internal Product and Engineering teams.
• Ensure Pencil's platform roadmap remains enterprise-ready by highlighting which capabilities are broken, which are missing, and which are driving immense value and deserve immediate capital investment.
• Systematically codify what works on your active accounts into highly structured, repeatable "Transformation Blueprints," ensuring every successful engagement leaves behind a sharper internal playbook for the global team.

Core Competencies & Evaluation Metrics

• Cognitive Process Mapping: The technical ability to analyze a client's legacy creative design and copywriting pipeline, identify automation entry points, and architect an AI-augmented replacement structure.
• Core Platform Competence: The technical agility to log directly into the software interface, understand its API capabilities, configure complex custom parameters, and validate infrastructure setups without relying on engineering support.
• Cross-Functional Articulation: The rare capacity to speak seamlessly across two distinct worlds—translating high-level creative vision to technical developers, and explaining complex model constraints or algorithmic features to non-technical creative directors.
• Institutional Change Hardening: Deep understanding of human behavior and corporate resistance patterns, applying structured frameworks to maintain user engagement and minimize platform churn during software updates.

Performance Success Vectors (KPIs)

• Enterprise Adoption Depth: Evaluated on the total depth, frequency, and functional breadth of Pencil usage across a customer’s diverse teams, regional offices, and digital marketing use cases once the rollout phase concludes.
• Time-to-Value (TTV) Optimization: Measured by the velocity at which your assigned corporate accounts achieve their first pre-defined technical success metrics or concrete financial ROI milestones post-kickoff.
• Quality of Transformation Narrative: Assessed by how cleanly your initial transformation thesis and strategic workstream planning survive delivery without requiring major re-architecting, paired with the long-term operational performance the recommendation yields for the client post-launch.
• Product Feedback Impact: Judged on the precision, structural quality, and enterprise reach of the operational insights you feed back to internal Engineering teams, directly shaping core application features.
• Blueprint Contribution Rate: Calculated based on your successful generation, formal documentation, and the internal team adoption of your repeatable "Transformation Blueprints" derived from real-world customer wins.

Skills Required:

• Computer / Software / It / Data
• Economics / Statistics
• Sales / Marketing / Business / Management