Head of Learning and Development

COMPANY OVERVIEWCraftwork is building a modern, technology-enabled home services company, starting with residential painting. We employ our painters full-time and manage the entire customer experience using proprietary software, which allows us to consistently deliver excellent quality and service while creating meaningful careers in the trades.Founded in 2023, Craftwork currently operates in Charlotte and Raleigh, with plans to expand into three new markets over the next 12 months. We’ve grown to nearly 80 employees and have raised over $25M from investors including Y Combinator, Seven Seven Six, Slow Ventures, Forerunner Ventures, General Catalyst, and Lachy Groom.POSITION OVERVIEWCraftwork is looking for a Head of Learning & Development to build the training and development function that will support our next stage of growth.As we expand into new markets and grow our field organization, our ability to consistently train great painters and operating leaders will become one of the most important drivers of our success. This person will create the systems that help every employee understand what excellence looks like, develop the skills required to achieve it, and see a clear path for continued growth at Craftwork.A central part of this mandate will be helping Craftwork train the next generation of professional painters. In partnership with our Head of Technical Training, this leader will develop an apprenticeship pathway for high-potential people entering the painting industry, combining structured learning, hands-on field experience, mentorship, and progressive skills validation. Our ambition is to give people a credible entry point into the trade and a clear path toward becoming highly skilled Craftworkers and future leaders.This is a hands-on, zero-to-one leadership role. The right person will be equally comfortable designing a company-wide learning strategy, developing training materials, facilitating sessions, coaching leaders, and spending time in the field to understand how the work actually gets done.The goal is not simply to create training programs. It’s to build a learning culture and a repeatable talent-development engine that improves quality, safety, customer experience, employee performance, and retention as Craftwork scales.OUTCOMESBuild Craftwork’s Learning & Development StrategyYou’ll develop a company-wide L&D roadmap that supports Craftwork's operating plan, market expansion, and hiring goals.You’ll define the roles and capabilities that require the greatest near-term investment.You’ll translate Craftwork’s standards and expectations into clear, teachable behaviors.Create Role-Based Onboarding & Development ProgramsYou’ll design and implement structured onboarding programs that help new employees become productive quickly and consistently.You’ll define the skills, standards, certifications, and practical assessments that verify the proficiency required for employees to operate independently.You’ll create a central, maintainable source of truth for curriculum, training materials, operating procedures, and role expectations.Launch Craftwork’s Apprenticeship PathwayYou’ll partner with the Head of Technical Training to design and launch Craftwork’s apprenticeship program for candidates without professional painting experience.You’ll build a progression model combining structured instruction, hands-on field experience, mentorship, observation, and demonstrated proficiency.You’ll demonstrate that Craftwork can develop promising, industry-new talent into safe, productive, quality-focused painters.Make Career Development Visible & MotivatingYou’ll create clear pathways that allow employees to understand their current level, the skills required to advance, and the opportunities available to them at Craftwork.You’ll introduce thoughtful incentives, recognition, and gamified elements that reward skill development and reinforce quality, productivity, teamwork, and customer service.You’ll help managers become more effective developers of their teams.Integrate Learning Into Craftwork’s SoftwareYou’ll partner with Product & Engineering to define the digital learning and development experience inside of Craftwork’s proprietary software.You’ll drive the development of functionality that provides employees with visibility into training assignments, skill development, individual progress, and their career pathway.You’ll test new functionality with employees in the field and use their feedback to iteratively improve the experience and impact.Build a Learning System That ScalesYou’ll establish a train-the-trainer program that equips managers, field leaders, and experienced painters with the tools to deliver consistent instruction across markets.You’ll connect development programs to measurable operating results, including quality, proficiency, productivity, engagement, advancement, and retention.You’ll continuously diagnose performance gaps and develop effective solutions.COMPETENCIESZero-to-One BuilderYou’ve built development programs for hourly, field-based, or skilled trade workforces.You can establish the strategy while personally building the initial programs.You bring structure to problems and turn broad objectives into repeatable systems.Frontline Learning ExpertiseYou understand that technical capability is developed through practice, coaching, observation, and demonstrated proficiency, and not through classroom content alone.You’re eager to spend meaningful time in the field learning from employees and understanding how the work is actually performed.Learning Design & FacilitationYou can demonstrate a strong knowledge of adult-learning principles, instructional design, facilitation, assessment, and program measurement.You can translate complex technical knowledge into clear, engaging, and practical learning experiences using hands-on instruction, on-site guidance, and visual content.Workforce & Career DevelopmentYou can define clear skill levels, certifications, assessments, and advancement criteria.You use recognition, incentives, and gamification thoughtfully to motivate development without compromising quality, safety, teamwork, or customer experience.Product & Technology OrientationYou understand how digital tools can support learning, progress visibility, certification, coaching, and career advancement.You use technology to reinforce hands-on development, not to replace it.Operational & Analytical JudgmentYou connect learning investments to measurable employee and business outcomes.You use data, field observation, manager feedback, and employee feedback to evaluate and improve programs, and to prioritize the work that will create the greatest impact.You distinguish skill or knowledge gaps from problems caused by management, process, tools, incentives, or role clarity.Collaborative LeadershipYou build trust and credibility with frontline employees, technical experts, managers, executives, and cross-functional partners.You approach subject-matter experts with humility and can turn their practical knowledge into scalable learning systems.You’re low ego, highly accountable, and genuinely motivated by helping others succeed.