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Transformation Lead

May 12, 2026

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.The Transformation Manager is a pivotal, provocative role designed to ensure our customers "get AI right" from day one. Acting as a bridge between initial interest and long-term enterprise-wide adoption, you will help potential and existing customers navigate the complexities of AI, establish robust success metrics, and manage the deep cultural and operational shifts required for true digital transformation. This isn't just about implementation; it's about leading a journey of change that prevents the painful "fix-it-later" scenarios common in rapid tech adoption by embedding Pencil’s values directly into the customer’s organizational DNA. <ul><li>Digital Transformation Expertise: Proven experience leading large-scale organizational change or digital transformation initiatives, ideally within a SaaS or consulting environment.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">AI & Data Literacy: Demonstrated ability to explain complex technical concepts (specifically AI) simply and define meaningful, measurable ROI metrics for executive stakeholders.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Commercial Experience: A background that includes selling or account growth, you are comfortable partnering with sales to close deals and/or expand existing customer footprints.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Customer Advisory: Experience acting as a strategic consultant or "trustworthy ally" to C-suite and departmental leads, building deep relationships based on value and expertise.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Process Codification: Experience in documenting and scaling best practices, turning individual customer successes into repeatable playbooks for a wider organization.</li></ul>You’ll Thrive Here If You…<ul><li dir="ltr" aria-level="1" style=" font-weight: 400;">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.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">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."</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Believe in Enterprise Adoption: You are obsessed with seeing technology move away from “pilot purgatory" and towards an embedded, value-driving part of a company’s culture and success.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">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.</li></ul>KPIs & Success Measures<ul><li dir="ltr" aria-level="1" style=" font-weight: 400;">Conversion Rate: Percentage of "testing" or "pilot" customers successfully converted to long-term enterprise licenses.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Enterprise Adoption Rate: Depth and breadth of Pencil usage across a customer’s various departments and teams post-onboarding.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Time-to-Value: Speed at which new customers reach their first defined "success metric" or ROI milestone.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Retention & Renewal: Long-term retention rates of accounts managed through the transformation process.</li><li dir="ltr" aria-level="1" style=" font-weight: 400;">Blueprint Contribution: Successful documentation and internal adoption of repeatable "Transformation Blueprints" based on customer wins.</li></ul> <ul><li>Strategic Onboarding & Advisory: Act as a trustworthy ally for new customers, guiding them to establish data-driven success metrics and helping them articulate the strategic benefits of Pencil within their specific business context.</li><li>Sales Partnership: Partner closely with Sales teams to convert prospects and testing customers into long-term enterprise licenses by demonstrating the roadmap for deep adoption.</li><li>Change Management Leadership: Lead customers through the journey of enterprise-wide transformation, moving beyond siloed use cases to integrated, AI-driven workflows while navigating complex stakeholder environments.</li><li>Stakeholder Navigation: Proactively identify and influence "blockers" and "champions" within a customer's organization to ensure smooth transitions and high-level buy-in for AI initiatives.</li><li>Product Feedback Loop: Act as the voice of the customer internally, feeding insights back to Product and Engineering to ensure the roadmap remains "enterprise-ready" and codifying "what works" into repeatable transformation blueprints.</li></ul> <ul><li>25 days PTO plus public holidays, although we operate a Flexible Time Off scheme</li><li>Health insurance / private medical cover</li><li>Monthly stipend towards wellness, fitness, and learning and development</li><li>Remote - work from anywhere in your home country </li><li>Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy </li><li>Access to our Pencil office in The Shard, London for UK employees</li><li>Flexible working hours</li></ul>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...