Lead, Project Management - Remote

Pencil; Philadelphia (Philadelphia County); Remote; USD 140,000 - 190,000; Full time

Benefits offered by this job

25 days PTO + public holidays

Health insurance / private medical

Remote - work from anywhere in home

Enhanced parental leave

Office access in London for UK staff

Flexible working hours

Job summary

Pencil is seeking a strategic and technical Transformation Consultant to lead enterprise AI-driven engagements on a defined set of accounts. You will own the transformation narrative, design blueprints, and partner with Forward Deployed Engineers and Creative Leads to drive programs from pilots to scale.

You will structure ambiguous problems, manage change, and translate needs into actionable steps, ensuring measurable impact and advancing Pencil's roadmap through customer feedback.

Qualifications

• 5+ years of consulting, agency, or enterprise transformation experience.
• Experience leading enterprise AI-driven transformation programs.

Responsibilities

• Own the narrative and strategic/tactical plan for client engagements.
• Structure ambiguous client problems into hypotheses, workstreams, and decisions.
• Lead change management to scale AI adoption across organizations.
• Provide product feedback insights to inform Pencil's roadmap.

Skills

Transformation leadership

Structured problem-solving

Change management

Client relationship management

SQL basics

Scripting

Education

Quantitative/analytical discipline degree

Tools

Pencil platform

Job description

At Pencil, we are driving innovation in advertising technology through our state-of-the-art SaaS product, which harnesses Generative AI to redefine content creation. Our mission is to make AI the default in advertising without replacing creative people. To achieve this, we need to make sure that our technology isn’t just in the hands of big brands - we need to try to help small businesses and creative individuals too.

You will be the strategic and technical owner of transformation engagements on a defined set of accounts.

• Implementation Leadership: Own the narrative told to the client and the strategic and tactical plan that drives the engagement, setting the transformation thesis, co-designing the recommendations with Forward Deployed Engineers and Creative Leads
• Structured Problem-Solving: Take ambiguous client problems and structure them from first principles into a clear set of hypotheses, workstreams, and sequenced decisions everyone can act on.
• Change Management Leadership: Lead clients through enterprise-wide transformation, moving them beyond siloed pilots into integrated, AI-driven workflows - navigating complex stakeholder landscapes, identifying blockers and champions, and engineering the buy-in that scaled AI adoption requires.
• AI Process Design: Product Feedback Loop: Act as the voice of the customer internally, feeding insights back to Product and Engineering - what's missing, what's broken, what's worth doubling down on - so Pencil's roadmap stays enterprise-ready.
• Transformation Blueprints: Codify what works on your accounts into repeatable Blueprints the rest of the team can run, so every successful engagement leaves behind a sharper playbook than the one before it.
• Minimum of 5 years’ experience in consulting or an agency setting, in-house transformation, programme management, or enterprise technology implementation, with exposure to technology, digital strategy, and/or operations. A strong academic record in a quantitative or analytical discipline is preferred.
• AI-native in your day-to-day. You're in the Pencil platform yourself - configuring agents, prototyping, stress-testing recommendations - and you can hold your own in a technical conversation with a client's engineers about their stack. Lightweight engineering - SQL, scripts, reading code - is a strong plus.
• You can carry a client meeting on your own, give direct feedback, and stay composed when scope shifts.
• Are Provocative and Brave: You aren't afraid to challenge a customer's existing way of working if it means helping them avoid long-term implementation challenges.
• Are an Ally to Change: You are comfortable with ambiguity and change, and you take pride in being a trustworthy partner who helps others navigate the "new and unknown."
• Embody Pencil Values: You lead with transparency, agility, and a focus on measurable impact, ensuring our values are mirrored in the customer’s own transformation journey.
• Depth and breadth of Pencil usage across a customer's teams, departments, and use cases once the rollout is live.
• Speed at which your accounts reach their first defined success metric or ROI milestone after engagement kickoff.
• Quality of Transformation Narrative: How well your transformation thesis and the strategic and tactical planning survive delivery without major rework, and the performance the recommendation drives for the client post-launch.
• Product Feedback Impact: Quality and reach of insights fed back to Product and Engineering that keep Pencil's roadmap enterprise-ready.
• Successful documentation and internal adoption of repeatable "Transformation Blueprints" based on customer wins.

• 25 days PTO plus public holidays, although we operate a Flexible Time Off scheme
• Health insurance / private medical cover
• Remote - work from anywhere in your home country
• Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy
• Access to our Pencil office in The Shard, London for UK employees
• Flexible working hours