Sr. Director, Business Development

Gwynnie Bee, New York, NY

Plus Size Clothing Subscription Boxes

About us:
Launched in 2012, Gwynnie Bee offers an unlimited-access clothing subscription service that utilizes innovative technology to transform the lives and wardrobes of women. Fueled by data, we challenge fashion’s status quo with our revolutionary subscription model that allows women to access and experience endless clothing styles without limitations or commitment.
Gwynnie Bee is an owned and operated tenant of CaaStle, a technology platform enabling retailers and brands to offer an unlimited-access clothing subscription service to complement existing business models.
Comprised of offices in New York City, Mountain View, New Delhi, Bangalore, and two distribution centers located in Groveport and Phoenix, at CaaStle you'll discover a data- centric team that thrives on collaboration, camaraderie, and productive feedback.

About the Role:

The Sr. Director of Business Development supporting CaaStle will be deployed to develop qualified prospects for the CaaStle platform. This person will be developing relationships with the c-suite of the world’s largest apparel manufacturers, utilizing best in class sales process and pipeline management, leveraging internal product specialists to accelerate the sales cycle, consistently closing new customer relationships, and collaborating with client service and account management teams to successfully onboard new clients.

We seek candidates who have excelled at driving adoption of new software and service solutions by the c-suite at Global 2000 companies.  If you’d like to demonstrate your entrepreneurial spirit and work in a hyper-growth environment in which the playbook for success is being built in real-time, read on.

What you’ll do:

  • Directly engage and build relationships with c-suite executives at leading apparel manufacturers via phone, in-person meetings and email
  • Articulate CaaStle’s premium brand, value proposition and product offering to qualify sales opportunities
  • Exhibit content mastery and command of topics important to executive leaders in apparel
  • Develop account plans for top-named prospects and strategies for a defined territory
  • Work creatively and collaboratively with internal colleagues in sales, marketing, legal, finance, product and technology to accelerate sales cycle and close new business
  • Represent the core values that underpin CaaStle’s culture and brand

We’d love for you to have:

  • 10+ years of experience selling software and/or services to the C-suite at Global 2000 companies
  • Bachelor's Degree required; JD/MBA preferred
  • Significant experience structuring and negotiating complex agreements and leading cross-functional groups to orchestrate and successfully complete deals
  • Distinctive track record of closing 6 and 7-figure contracts while exceeding quota consistently
  • Superior written/oral communications skills and presentation skills

In addition, we seek bright, positive and flexible people who:

  • Are motivated by the chase of the hunt in all things "new business"
  • Are resilient, perseverant and goal-oriented
  • Are strong independent players who also add value to a collaborative team atmosphere
  • Exhibit process discipline and systematic approach to pipeline development

Key performance metrics for this role include core sales activities (e.g., outreach, meetings, new client acquisition) and opportunity/pipeline management to create transparent and predictable new sales forecasts.

Candidates for this position should have a demonstrated ability to be creative and commercial and/or have a track record of overachieving in a performance-based environment, preferably but not exclusively, in the technology or services sector.  

CaaStle is committed to equality of opportunity in employment. It has been and will continue to be the policy of CaaStle to provide full and equal employment opportunities to all employees and candidates for employment without regard to race, color, religion, national or ethnic origin, veteran status, age, sexual orientation, gender identity, or physical or mental disability. This policy applies to all terms, conditions and privileges of employment, such as those pertaining to training, transfer, promotion, compensation and recreational programs.

About Gwynnie Bee

WELCOME TO GWYNNIE BEE & YOUR NEW CLOSET More than five years ago, a few of us came together on a mission to create an exciting new service that helps women discover, experience, and enjoy great clothing without limitations. We believe that fashion has the ability to transform your sense of self–to make you look stunning and feel just as amazing. When I was a little girl growing up in rural Pennsylvania, my aunt made all of my clothing for me. Every Monday I had a fresh box of clothes for the week. Bright prints, matching separates, trendy styles—you name it, I wore it! They always fit and made me feel confident even as I was changing size. Traditional shopping means considering all the limiting factors—how often you will wear each garment, whether it will match your wardrobe or go out of style, and the stress of finding the right fit when you change a size. We hope to deliver all the great things that fashion has to offer, without all the stress. Welcome to the Gwynnie Bee family. With Love, Christine

Want to learn more about Gwynnie Bee? Visit Gwynnie Bee's website.