Head of Learning and Development

Craftwork 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.

Craftwork 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 Craft workers 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.

• You’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.

• You’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.

• You’ll partner with 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.
• You’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…