Business Development Representative

Cherry Willow Apparel is building something bigger than fashion. We connect schools, organizations, and communities through custom apparel while supporting a mission that amplifies the voices of people experiencing homelessness and our nonprofit partners.

We’re looking for a Business Development Representative who can open doors, build relationships, and turn new opportunities into lasting school partnerships. You’ll help schools meet their apparel and fundraising needs while growing a business with a meaningful community purpose.

This is a hands-on, full-cycle sales role—not an appointment-setting-only position. You’ll own the relationship from the first conversation through the sale, then help identify opportunities for repeat business and growth.

You’ll work closely with leadership to develop new school partnerships, build a strong sales pipeline, and turn Cherry Willow’s capabilities and mission into a compelling reason to do business with us.

• Find and develop new business. Identify and engage schools, athletic programs, booster clubs, student organizations, and other school-affiliated groups with custom apparel needs.
• Connect with decision-makers. Build relationships with athletic directors, principals, coaches, activities directors, booster-club leaders, and purchasing contacts through calls, email, networking, referrals, and meetings.
• Understand each school’s needs. Ask thoughtful questions about existing apparel programs, purchasing timelines, fundraising goals, budgets, and opportunities to improve their experience.
• Manage the sales process. Lead discovery conversations, coordinate proposals and pricing with the team, follow up consistently, address concerns, and close new partnerships.
• Help new accounts get started successfully. Coordinate with internal teams to move signed partnerships into active programs and paid orders, with clear expectations and a smooth handoff.
• Build relationships that lead to repeat business. Stay connected with key contacts, identify additional departments and programs, and support renewals and account expansion.
• Keep your pipeline organized. Maintain accurate customer relationship management records, communicate next steps, forecast opportunities, and work with leadership to improve results.

You’ll own acquisition and strategic account relationships, while our service and production teams handle routine fulfillment.

• 1–2 years of experience in business development, outside sales, business-to-business sales, or a related role— or a strong combination of aptitude, drive, and willingness to learn. Prior sales experience is helpful, but we’re equally interested in someone who can learn the role, take initiative, and put in the work to succeed.
• A demonstrated history of winning new accounts and producing measurable results—not just generating activity or scheduling meetings.
• Someone comfortable initiating conversations, making outbound calls, following up, handling objections, and asking for the business.
• Strong communication and relationship-building skills, with the ability to connect a customer’s practical needs to a compelling solution.
• An organized, reliable, self-directed professional who can manage multiple opportunities, maintain accurate records, and take ownership of results.
• A genuine connection to our mission and a desire to build a business that contributes to stronger communities.

Experience selling to schools, districts, athletic programs, booster organizations, or other education-related buyers is especially valuable. Experience in custom apparel, screen printing, promotional products, or fundraising programs is a plus.

You’re not just selling apparel. You’re helping schools bring their communities together, support their programs, and choose a partner whose work connects to a broader mission.

You’ll have the opportunity to help shape how Cherry Willow develops school partnerships, work directly with leadership, and build a book of business you can continue to grow. We’re looking for someone who enjoys opening doors and earning trust—not simply processing orders that are already coming in.

This role begins with a commission-based launch phase, with no initial base salary and a defined path to a base-plus-performance compensation structure.

• Uncapped new-account commissions: During the initial phase, earn 25% of commissionable gross profit on collected revenue during each qualifying new school account’s first 12 months.
• Early account earnings: The initial $500 activation incentive is payable in advance as a draw for each qualifying new school account and becomes earned when that account reaches its first $5,000 in collected revenue. This is an advance against the incentive, not an additional payment. An additional $500 development bonus is earned when the account reaches $10,000 in collected revenue.
• Repeat-business compensation: Earn 5% of commissionable gross profit on qualifying repeat revenue during the account’s second year, subject to the written compensation plan. Approved selling expenses are reimbursed separately.
• Base-salary transition: After achieving defined account, collected-revenue, profitability, and operating milestones, the role transitions to a base salary plus revised commissions and bonuses. The updated target total compensation is approximately $64,000–$70,000 annually .

Target compensation is not a guaranteed salary or earnings amount. Full details—including draw terms, qualification requirements, payment timing, and transition milestones—will be provided in the written compensation plan.

Within your first year, you’ll help establish a strong portfolio of school partnerships that generates collected revenue, repeat business, and opportunities for continued growth.

Our first-year objective is approximately 18–24 activated school accounts , supported by a healthy pipeline and disciplined account management.

Success means more than getting a school to sign an agreement. It means helping that school launch a program, place orders, have a positive experience, and see a reason to work with Cherry Willow again.

You’ll build trusted relationships, uncover expansion opportunities, maintain accurate forecasts, and coordinate effectively with our internal teams. We value consistent prospecting and follow-through, but the ultimate measure is the quality and growth of the business you build.