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Cosmetologist / Hair Stylist Educator / Trainer

WellBiz Brands•Boston, MA
•Onsite

About The Position

Drybar Back Bay is seeking a Shop Educator to help develop the team at its Chestnut Hill location. The role combines hairstyling with training, coaching, recruitment, sales support, and team development. Drybar focuses on blowouts and does not offer cuts or color. The Shop Educator helps newly hired stylists learn Drybar techniques, service standards, timing expectations, and client experience, then supports their ongoing development and performance. The role also promotes sales and client retention, builds relationships with local cosmetology and beauty schools, and partners with shop and regional leadership to align training with business goals. Compensation may include base pay, tips, and commissions; the posting says stylists and leads may earn up to $40+ per hour in total compensation, with top-performing stylists earning $50+ per hour.

Requirements

  • Valid Massachusetts cosmetology license.
  • Strong styling and finishing skills.
  • Excellent communication, organization, and follow-through.
  • Passion for teaching and developing people.
  • Comfort providing constructive feedback and holding others accountable.
  • Ability to work in a fast-paced environment and solve problems.
  • Willingness to celebrate team wins and provide additional coaching when needed.

Responsibilities

  • Train and onboard newly hired stylists in Drybar techniques, service standards, timing expectations, and client experience.
  • Monitor trainee performance after initial training to support consistency and continued development.
  • Conduct one-on-one coaching sessions with new hires, recognizing successes and addressing areas for improvement.
  • Participate in 30-, 60-, and 90-day check-ins with new hires, establish goals, and follow up on progress.
  • Identify stylists who need additional education, coaching, or hands-on support.
  • Build relationships with local cosmetology and beauty schools to create recruitment opportunities and a pipeline of future stylists.
  • Participate in school outreach, recruiting events, and communication with upcoming graduates.
  • Coach the team on memberships, retail, add-ons, rebooking, and overall client experience to help create a strong sales culture.
  • Lead by example and demonstrate expected performance, professionalism, and accountability.
  • Provide weekly updates to upper management on trainee progress, opportunities, training goals, team development, and sales performance.
  • Partner with shop and regional leadership to ensure training priorities support business goals.
  • Work behind the chair while carrying out training and team-development responsibilities.

Benefits

  • Employee retail discounts.
  • Continued professional development.
  • Opportunities for leadership advancement.
  • Opportunity to earn tips, commissions, and sales incentives; stylists and leads may earn up to $40+ per hour in total compensation, and top-performing stylists may earn $50+ per hour.
  • Keep 100% of tips.
  • Team contests and incentives.

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