Founding Product Designer (£80-110K) at Chalkie

📍 Job Overview

Job Title: Founding Product Designer

Company: Chalkie (Recruited by Jack & Jill)

Location: Remote (United Kingdom)

Job Type: FULL_TIME

Category: Product Design / Product Management (Hybrid)

Date Posted: 2026-04-22

Experience Level: 4-7 Years

Remote Status: Fully Remote

🚀 Role Summary

• This is a pivotal Founding Product Designer role within a fast-growing, seed-funded EdTech startup, offering significant influence on product direction and design standards.

• The role requires ownership of product areas end-to-end, blending product design and product management responsibilities, with a strong emphasis on leveraging AI-first workflows.

• You will be instrumental in shaping the future of classroom technology, impacting over one million teachers globally through the creation of simple, impactful tools.

• This position offers a unique opportunity to work directly with the CPO and engineering teams in a high-velocity environment, utilizing cutting-edge AI tools for rapid development cycles.

📝 Enhancement Note: The job description emphasizes a hybrid role between Product Design and Product Management, suggesting the need for strong strategic thinking, user empathy, and the ability to translate business needs into user-centric solutions. The "founding" aspect implies a need for initiative, adaptability, and a proactive approach to establishing design foundations.

📈 Primary Responsibilities

• Own product work end-to-end, from ideation and exploration to definition and shipping improvements that critically impact key business metrics.

• Serve as both a product designer and product manager, collaborating closely with the Chief Product Officer (CPO) and engineering teams to define product strategy and roadmap.

• Utilize AI tools such as Cursor and Claude daily for rapid prototyping, clarifying user intent, and directly building interfaces within the codebase, accelerating the development lifecycle.

• Conduct weekly user research sessions with a substantial subscriber base (50,000+ paying subscribers) to validate product hypotheses, gather feedback, and ensure exceptional product simplicity and usability.

• Establish and champion the design patterns, principles, and overall quality bar for the entire company, acting as the second designer and setting the visual and interaction design direction.

• Partner with engineering to translate user needs and business goals into intuitive and effective user interfaces and experiences.

📝 Enhancement Note: The responsibilities clearly indicate a hands-on role that requires not only design execution but also strategic product thinking and a deep understanding of user needs. The emphasis on AI tools suggests a need for adaptability and a willingness to embrace new technologies in the design process.

🎓 Skills & Qualifications

Education:

Experience:

• 4-7 years of dedicated product design experience, ideally within a fast-paced, high-growth startup environment.

• Proven track record of owning product areas end-to-end and successfully shipping impactful design solutions.

Required Skills:

• Product Design: Expertise in the full product design lifecycle, including user research, wireframing, prototyping, and high-fidelity UI design.

• UX Design: Deep understanding of user experience principles, usability testing, and creating intuitive, user-centered solutions.

• Product Management Acumen: Ability to think strategically, define product requirements, prioritize features, and collaborate effectively with product leadership.

• AI Tool Proficiency: Hands-on experience or a strong aptitude for using AI tools like Cursor and Claude for design and development tasks.

• Prototyping: Skill in creating interactive prototypes to effectively communicate design concepts and gather user feedback.

Preferred Skills:

• User Research: Experience conducting qualitative and quantitative user research, including interviews, surveys, and usability testing.

• Interface Design: A keen eye for visual design, branding, and creating aesthetically pleasing and functional interfaces.

• EdTech Domain Knowledge: Familiarity with the education technology landscape, user needs of teachers, and the challenges within the education sector.

• Codebase Interaction: Willingness and ability to work directly within a codebase, leveraging AI tools for faster iteration.

• Data Analysis: Ability to interpret user data and metrics to inform design decisions and measure impact.

📝 Enhancement Note: The experience requirement of 4-7 years, combined with the "founding" nature of the role, suggests the need for a candidate who is not only skilled but also capable of establishing foundational design practices and acting with a degree of autonomy. The emphasis on AI suggests a forward-thinking candidate who is eager to leverage emerging technologies.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing end-to-end product design ownership, demonstrating impact and problem-solving skills.

• Clear examples of UX craft, aesthetic taste, and meticulous attention to detail in past projects.

• Case studies that highlight the candidate's ability to leverage AI-first workflows or similar rapid development methodologies in their design process.

• Evidence of strong collaboration with engineering and product teams, illustrating how design solutions were integrated into the product.

Process Documentation:

• Showcase a structured approach to design problem-solving, from initial user needs analysis to final implementation and iteration.

• Detail how you have used AI tools or other rapid prototyping methods to accelerate design cycles and validate concepts.

• Provide examples of how you have established or contributed to design systems, patterns, and style guides in previous roles, particularly in startup environments.

• Illustrate your process for conducting and synthesizing user research, and how this feedback loop influenced product direction and feature development.

📝 Enhancement Note: Given this is a founding role, the portfolio should emphasize not just execution but also the ability to define and implement design processes and standards from the ground up. The inclusion of AI tools in the portfolio is crucial, showcasing practical application and understanding.

💵 Compensation & Benefits

Salary Range: £80,000 - £110,000 per annum

Benefits:

• Significant Equity/Stock Options: As a founding team member, expect substantial equity, reflecting the early-stage nature of the company and the impact of this role.

• Comprehensive Health Coverage: Likely includes private medical insurance, dental, and vision coverage, tailored for UK-based employees.

• Generous Paid Time Off: A competitive annual leave allowance, likely exceeding statutory minimums, to promote work-life balance.

• Professional Development Budget: A dedicated budget for learning and development, including conferences, courses, and resources to enhance skills in product design, AI, and product management.

• Remote Work Stipend: A budget or allowance to equip a home office, ensuring a productive and comfortable remote work environment.

• Pension Scheme: A company-contributed pension plan to support long-term financial security.

Working Hours:

• Standard full-time hours, typically around 40 hours per week. However, the high-velocity, AI-first culture may imply flexibility and a focus on output rather than strict adherence to hours, especially given the remote nature.

📝 Enhancement Note: The salary range provided is competitive for a senior/founding Product Designer role in London, especially within a startup environment. The inclusion of significant equity is a standard offering for such positions, highlighting the opportunity for substantial financial reward tied to company growth. The benefits package is assumed to be comprehensive, aligning with typical offerings for UK tech startups aiming to attract top talent.

🎯 Team & Company Context

🏢 Company Culture

Industry: EdTech (Education Technology)

Company Size: Seed-funded startup, likely small to medium-sized (less than 50 employees), with potential for rapid scaling.

Founded: Recently founded, aiming to disrupt the education sector with AI-driven solutions.

Team Structure:

• The design team currently consists of this founding product designer and reports directly to the Chief Product Officer (CPO).

• This role will work closely with a lean but highly effective engineering team.

Methodology:

• AI-First Workflows: A core operational methodology, emphasizing the use of AI tools (e.g., Cursor, Claude) to accelerate development cycles from concept to production.

• High-Velocity Product Development: A culture that prioritizes rapid iteration, testing, and deployment to quickly respond to user feedback and market opportunities.

• Data-Driven Decision Making: While qualitative feedback is crucial (weekly research sessions), decisions are informed by both user insights and key performance metrics.

• User-Centric Design: A commitment to understanding and serving the needs of over one million teachers worldwide, ensuring simplicity and impact in all product offerings.

Company Website: https://www.jackandjill.ai/ (Note: This is the recruitment platform's website, not Chalkie's. Chalkie's specific URL is not provided but implied to be within the EdTech space.)

📝 Enhancement Note: The company culture is described as high-velocity and AI-first, suggesting a dynamic and innovative environment. As a founding designer, you'll be key in establishing the design culture and processes within this rapidly evolving startup.

📈 Career & Growth Analysis

Operations Career Level: Founding Product Designer / Senior Product Designer

This role is positioned at a senior level, offering the unique opportunity to be a foundational member of the design team. It goes beyond typical senior designer responsibilities by incorporating significant product management duties and the chance to define design strategy from its inception.

Reporting Structure:

• You will report directly to the Chief Product Officer (CPO), providing a direct line of communication and influence on product strategy and vision.

Operations Impact:

• This role has a direct and substantial impact on Chalkie's product roadmap, user experience, and overall market positioning within the EdTech sector.

Growth Opportunities:

• Design Leadership: Potential to grow into a Head of Design or Design Lead role as the company scales, building and managing a design team.

• Product Management Specialization: Opportunity to deepen product management skills and potentially transition into a dedicated Product Manager role if desired.

• AI & Technology Expertise: Develop deep expertise in AI-first design and development workflows, becoming a leader in this emerging field within EdTech.

• Strategic Impact: Contribute to key business decisions and company strategy, gaining broad exposure to startup growth levers.

• Mentorship: As the team grows, opportunities to mentor junior designers and establish best practices.

📝 Enhancement Note: The "founding" nature of this role implies significant growth potential, not just in terms of career progression but also in the scope of responsibility and influence. Candidates should be prepared for a challenging but rewarding journey of building a product and a design function from the ground up.

🌐 Work Environment

Office Type: Fully Remote

This role is entirely remote, offering flexibility and the ability to work from anywhere within the United Kingdom.

Office Location(s):

Workspace Context:

• Collaborative Digital Environment: Expect a highly collaborative remote setup, utilizing digital tools for communication, design, and project management. Regular video calls and asynchronous communication will be key.

• Access to Cutting-Edge Tools: The environment is characterized by the use of advanced AI tools (Cursor, Claude) integrated into the development workflow, providing designers with powerful capabilities.

• High-Paced Iteration: The workspace is geared towards rapid iteration and experimentation, encouraging quick feedback loops and agile methodologies.

• Direct Stakeholder Interaction: Opportunities for frequent interaction with the CPO, engineering, and potentially even direct engagement with a large user base.

Work Schedule:

• Standard full-time working hours (approx. 40 hours/week) are expected, but the remote and startup nature may offer some flexibility. The focus is likely on delivering results and meeting project deadlines rather than strict time adherence. Occasional overlap with engineering and CPO schedules will be necessary.

📝 Enhancement Note: As a remote role, the emphasis will be on effective communication, self-discipline, and leveraging digital collaboration tools. The company's AI-first approach suggests a modern, technologically advanced work environment, even though it's remote.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening (Jack & Jill): A preliminary conversation with "Jack" (the AI recruitment assistant) to understand your experience, career aspirations, and suitability for the role. This is designed to be a quick, personalized assessment.

• Introduction to Jill: If Jack identifies a strong match, your profile is presented to "Jill" (the AI Recruiter for Chalkie).

• Company Screening: If Jill deems you a good fit, you will likely have an initial screening call with the CPO or a hiring manager at Chalkie. This will focus on your background, design philosophy, and understanding of their mission.

• Design Challenge/Portfolio Review: A core part of the process will involve presenting your portfolio. You may be given a specific design challenge or asked to walk through key projects from your portfolio, detailing your process, decision-making, and impact. Expect questions about your experience with AI tools and high-velocity development.

• Team Interviews: Interviews with engineering leads or other founding team members to assess cultural fit, collaboration style, and technical understanding.

• Final Interview: Potentially a final discussion with the CEO or CPO to discuss vision, long-term impact, and offer details.

Portfolio Review Tips:

• Highlight AI Integration: Explicitly showcase projects where you've used AI tools or experimental workflows. Detail the benefits and challenges encountered.

• End-to-End Ownership: Focus on case studies where you've taken full ownership of a product area, demonstrating strategic thinking, problem-solving, and execution from conception to launch.

• Quantify Impact: Wherever possible, use metrics (£400k MRR, user numbers, engagement rates) to demonstrate the tangible impact of your design decisions.

• Showcase UX Craft & Taste: Ensure your portfolio exhibits strong visual design skills, attention to detail, and a clear understanding of user-centered design principles.

• Explain Your Process: Clearly articulate your design process, including how you conduct user research, iterate on designs, and collaborate with cross-functional teams.

• Tailor to EdTech: If possible, include projects relevant to the EdTech space or demonstrate an understanding of the unique challenges and opportunities within this sector.

Challenge Preparation:

• Be prepared to discuss how you would approach designing for a rapidly scaling EdTech product, considering the needs of teachers and students.

• Anticipate questions about your experience with AI-driven design tools and how you envision their role in product development.

• Practice articulating your design rationale clearly and concisely, as you will need to justify your decisions effectively.

• Be ready to discuss how you would establish design standards and processes for a new product function.

📝 Enhancement Note: The application process is unique, leveraging AI assistants for initial screening. Candidates should be prepared for a robust portfolio review and interviews that assess both design skills and strategic product thinking, with a strong emphasis on AI and startup environments.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma, Sketch, Adobe Creative Suite (standard tools for UI/UX design).

• AI-Assisted Design/Development: Cursor (AI-powered code editor), Claude (AI assistant for coding and design ideation).

• User Research Platforms: Tools for conducting remote interviews, surveys, and usability testing (e.g., UserTesting.com, SurveyMonkey, Maze).

Analytics & Reporting:

• Product Analytics: Tools like Amplitude, Mixpanel, or Pendo to track user behavior, engagement, and feature adoption.

• Business Intelligence: Potentially basic BI tools for understanding MRR, user growth, and other key business metrics.

CRM & Automation:

• While not directly a CRM role, understanding how design impacts user onboarding and retention within a CRM context might be beneficial.

• Project Management: Tools like Jira, Asana, Trello for managing product development workflows and tasks.

Codebase Interaction:

• While not expected to be a developer, the role requires comfort and ability to interact with code and use AI tools directly within the development environment (e.g., Cursor).

📝 Enhancement Note: The emphasis on AI tools like Cursor and Claude is a significant differentiator. Candidates should highlight any experience or strong interest in leveraging these technologies for design and development acceleration. Familiarity with standard product design tools is a given, but the ability to integrate AI into the workflow is key.

👥 Team Culture & Values

Operations Values:

• Innovation & AI Adoption: A genuine embrace of cutting-edge technology, particularly AI, to drive efficiency and build better products.

• Velocity & Agility: A commitment to moving fast, iterating quickly, and adapting to change in a dynamic startup environment.

• User-Centricity: A deep focus on understanding and serving the needs of teachers and students, ensuring products are simple, impactful, and usable.

• Ownership & Impact: A culture where individuals take full responsibility for their work and are driven to make a significant contribution to the company's success.

• Collaboration & Transparency: Open communication and a willingness to work closely with all team members, sharing knowledge and feedback constructively.

Collaboration Style:

• Remote-First Collaboration: Utilizing digital tools and asynchronous communication effectively to maintain seamless collaboration across the team.

• Cross-Functional Partnership: Working hand-in-hand with product leadership and engineering to ensure alignment and drive cohesive product development.

• Feedback-Rich Environment: Encouraging regular feedback exchange, both formally through research sessions and informally within the team, to foster continuous improvement.

• Empowerment and Autonomy: A culture that empowers individuals to take initiative and make decisions within their areas of responsibility.

📝 Enhancement Note: The company culture appears to be a blend of modern startup ethos (fast-paced, AI-driven, remote) and a strong mission-oriented focus (EdTech, user impact). Candidates should demonstrate an alignment with these values and a proactive approach to collaboration.

⚡ Challenges & Growth Opportunities

Challenges:

• Establishing Design Foundation: As the second designer, you'll be responsible for setting up critical design processes, patterns, and principles from the ground up, requiring strong strategic thinking and execution.

• Balancing Design and PM: Effectively managing the dual responsibilities of product design and product management in a high-velocity environment will require excellent time management and prioritization skills.

• AI Integration Learning Curve: While AI tools offer significant advantages, mastering their integration into a design workflow may present an initial learning curve.

• Remote Collaboration Dynamics: Navigating effective communication and collaboration within a fully remote team requires proactive effort and excellent digital communication skills.

• Scaling Design Ops: As the company grows, you'll need to anticipate and plan for scaling design operations, processes, and potentially team growth.

Learning & Development Opportunities:

• Mastering AI in Design: Deepen your expertise in leveraging AI tools for design and development, becoming a leader in this rapidly evolving field.

• Product Strategy & Management: Gain invaluable experience in product strategy, roadmap planning, and user research at a senior level within a fast-growing startup.

• Building Design Systems: Develop and implement robust design systems and style guides that will scale with the company.

• Leadership Potential: Opportunity to grow into a leadership role, potentially managing a design team and influencing company-wide product direction.

• EdTech Industry Expertise: Gain deep insights into the EdTech market, user needs, and the impact of technology on education.

📝 Enhancement Note: The challenges presented are typical of a founding role in a startup, offering significant opportunities for personal and professional growth. Candidates who thrive in ambiguity and are eager to build something from the ground up will find this role particularly rewarding.

💡 Interview Preparation

Strategy Questions:

• "How would you approach establishing the design principles and patterns for a new EdTech product aiming for global reach?" - Prepare to discuss your process for defining design systems and ensuring brand consistency.

• "Describe a situation where you had to balance product management responsibilities with your design work. How did you prioritize and manage your time?" - Focus on your ability to manage competing demands and deliver results across different functions.

Company & Culture Questions:

• "What interests you most about Chalkie's mission and its use of AI in EdTech?" - Research the company's mission and the broader EdTech landscape. Connect your passion to their goals.

• "How do you approach collaboration in a fully remote environment, especially with engineering and product teams?" - Highlight your communication strategies, experience with remote tools, and proactive approach to teamwork.

Portfolio Presentation Strategy:

• Storytelling with Data: Structure your portfolio case studies as compelling narratives, clearly defining the problem, your approach, the solution, and the measurable impact. Use metrics like MRR and user numbers to quantify success.

• Demonstrate AI Workflow: Visually or verbally explain how AI tools were integrated into your design process for specific projects. Showcase the efficiency gains or innovative outcomes.

• End-to-End Ownership Examples: Prioritize projects where you had full autonomy and ownership, showcasing your ability to drive initiatives from start to finish.

• User Empathy in Action: Clearly articulate how user research informed your design decisions and led to improved user experiences.

• Concise and Focused: Be prepared to present your most impactful projects concisely, focusing on the most relevant aspects for this role.

📝 Enhancement Note: Interview preparation should focus on demonstrating a blend of strong design craft, strategic product thinking, comfort with AI technologies, and an entrepreneurial mindset suitable for a founding role in a fast-paced startup.

📌 Application Steps

To apply for this operations position:

• Visit the Jack & Jill website (https://jackandjill.ai/) and click on 'Talk to Jack'.

• Prepare for your 'Talk to Jack' session: Be ready to articulate your key strengths, career ambitions, and why you are a strong fit for a founding Product Designer role in an AI-first EdTech startup, highlighting your experience with AI tools and product ownership.

• Optimize your CV for Operations Roles: Ensure your resume clearly lists your experience in product design, product management, UX, AI tool usage, and any relevant startup or EdTech experience. Quantify achievements with metrics where possible.

• Curate Your Portfolio Strategically: Select 3-4 of your strongest case studies that best demonstrate end-to-end ownership, AI integration, and impact. Prepare to walk through them, focusing on your process, decision-making, and results.

• Research Chalkie and the EdTech Landscape: Understand Chalkie's mission and the broader context of AI in education. Be ready to discuss how your skills align with their goals and the challenges of the EdTech market.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.