Role Overview

Drawing Room currently enrolls more than 100 adult students each Journey season, across 5+ concurrent programs. These numbers are projected to grow significantly over the next year. We are building a brand that provides the space, tools, knowledge, and community to inspire and support creative living. Our definition of creative living includes making, writing, discussing, sculpting, and painting, and may expand into new areas such as movement, philosophy, and other yet-to-be-explored mediums.

Our learning arm is central to realizing this mission: developing creative confidence requires structured opportunities to learn, practice, and explore. 

This role serves as the business owner and strategic leader for all things “learning” at Drawing Room. You will own the success and full life-cycle execution of all Drawing Room learning offerings – Journeys, seasonal initiatives, and all the systems, logistics, and operations that make these happen.You will lead and grow the team responsible for delivering these experiences, and collaborate closely with instructors and cross-functional partners, including inventory, community experience, marketing, and more, to ensure that our programming continues to scale, evolve, and delight our learners.

Role logistics:

• Non-exempt, hourly role

• This is an approximately 30-40 hour per week role at $30-$35 per hour. Compensation within this range will be determined based on prior experience managing programs, people, and operational complexity.

• The start date is flexible, with a strong preference for someone who can start soon.

• In-person role, with 4-5 regularly committed weekdays

• Mondays are in-person team days in Midtown

• Tuesdays are in-person team days at Williamsburg

• Drop into 3-4 workshops/events per month, which occur during weekday evenings and weekends. Also include Drawing Room Nights (Friday evenings) and Cohort Orientation/Showcases (weekday evenings). 

• All remaining hours are in-person during weekdays. Remote hours occasionally permitted.

Key Responsibilities

Successful business outcomes 

• Own business success metrics around Journey/workshop quality (reviews, retention, LTV, referrals, etc), profit/margins, and growth rate

• End to end from development oversight to describing, distilling, and launching the product on website and across marketing 

• Being involved in the development process and being able to turn this into a product in collaboration with instructor team 

• Strategic development in partnership with the team of teaching artists. 

• Able to listen, learn, and understand, weaving together customer feedback you hear through your own conversations with the community, instructors, our hosts, etc. and combining that with business needs  

• Relying on the instructor team to bring expertise around creative skill/learning & they are most intimately familiar with our community/customers 

• Responsible for journey related budget (team, materials, etc) 

• Responsible for programming performance metrics such as sales, retention, etc 

• Partner with other parts of the organization to understand the user journey and deliver on an effective experience/lifecycle for our customers. For example, how do Journey participants become members and then sign up for another Journey in the future? 

Program Quality & Execution

• Understand our customers extremely well and be their fiercest advocate. Build relationships and have a direct line of communication with our community members and customers. Lean on instructors for the strong feedback loop with our learning community. 

• Own end-to-end production and success of inventory logistics, working with purchasing stakeholders to ensure operational smoothness.

• Schedule workshops according to staffing needs 

• Set up Journeys and workshops on Momence, our membership management system 

• Optimize logistics processes 

• Ensure seamless customer / community experience (e.g., ceramics assembly, firing timelines) and ensure customer satisfaction from end to end 

• Ensuring we paying vendors like figure models in a timely manner  

• Responsible for overseeing the Journey Bulletin and related documentation. 

Launch / Project Management

• Drive launches of seasonal journeys and cross-team coordination to meet deadlines and quality standards.

• Review and refine content, copy, and experience details.

• Own and optimize new programming development and launch cycles, from pitch to launch and marketing on public channels and catalogs. 

• Implement optimizations (e.g., timing adjustments to increase sales).

Team Leadership & Development

• Manage, mentor, and scale the instructor team.

• Define instructor roles and build clear career progressions.

• Lead hiring, onboarding, pay rate structures, and performance management.

• Own and conduct monthly team meetings, weekly communications, and feedback cycles.

• Identify emerging leaders; provide coaching and shadowing opportunities.

• Restructure existing roles and integrate review systems.

Growth & Retention

• Collaborate with Marketing on promotions and communications.

• Own journey-related business metrics, reporting, and insights.

• Manage pricing strategy for programs and workshops.

• Defining engagement and retention success for our journey customers (ie. engaging with them on social? discord?) 

• Where are people converting from? What’s working and what does successful lifecycle look like? How are instructors or other team members supporting this lifecycle journey? Collaborating with our team to identify, understand and improve our offerings. 

• Identify and explore other opportunities such as digital programming, retail workshop kits, and much more.

Ideal Qualifications

• 4+ years experience executing and supporting complex programs or learning initiatives

• 2+ years managing people, including scheduling, onboarding, and feedback

• Strong operational background across scheduling, inventory, logistics, and documentation

• Experience contributing to program performance metrics such as enrollment, retention, and quality

• Ability to turn creative ideas into clear, structured offerings and timelines

• Comfort working in fast growing, low infrastructure environments

• Strong attention to detail and follow through

• Experience collaborating with instructors or facilitators

• Respect for creative education and adult learning

• Strong written and verbal communication skills

• Availability for in person weekdays plus occasional evenings and weekends

You will be successful in this role if:

• You are a strong executor who brings structure to creative programs

• You take ownership of day to day execution while collaborating on strategy

• You manage people with clarity and care

• You adapt quickly and stay steady as things change

• You care deeply about quality and experience details

• You are invested in Drawing Room’s mission and excited to grow with it

Benefits: 

• Paid sick leave (up to 40 hours per year, accrued hourly)

• Drawing Room Staff membership including workshops, free access to all gatherings, guest passes, team discounts, and more.

Build Phase Context

Drawing Room is currently in a build phase. As a small and growing organization, we do not yet offer health benefits for part-time roles. This role is intentionally scoped to fit within that reality.

As we continue to stabilize and grow, we expect to revisit role structures, compensation, and benefits. This position may evolve over time as the organization matures, though there is no guarantee of expansion or conversion. We aim to be transparent, fair, and thoughtful as we build toward greater sustainability.

This role is ideal for a candidate who is energized by early-stage building, comfortable with ambiguity, and motivated by long-term impact rather than immediate infrastructure.