Director, People Operations and Rewards

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.


Reporting to the Head of People, this new position serves as the Total Rewards and People Operations lead for CaaStle. The right candidate will build and scale our Global Total Rewards Program, which includes designing and analyzing compensation and benefits to align to business objectives. In addition, this person will be responsible for leading the transformation of People Operations data, insights, systems and processes to streamline, simplify and standardize and improve the employee and candidate experience.

What you’ll do:

Total Rewards:

  • Own the strategy and build out of the Global Total Rewards strategy and supporting programs for benchmarking, total compensations, equity, sales commission, and benefits that create a compelling employee value proposition for all employees
  • Define and run company wide compensation processes aligned to performance philosophy and company culture
  • Advise and train People Team, managers and employees on Total Rewards philosophy and programs. Serve as the company’s benefits expert
  • Lead market and ad-hoc analyses of base pay, variable pay, equity and benefits to ensure market competitiveness and identify issues
  • Initiate and deliver specialized analysis on competitive and internal compensation practices, strategies and metrics based on business need
  • Anticipate, innovate and respond quickly as business and market realities change, staying current on best practices and trends; ensure compliance with applicable legislation

People Operations:

  • Create and manage a new People Operations function beginning with needs analysis to support a fast growing global company
  • Select and manage the array of vendors, third party tools and IT requirements  
  • Manage the People Operations function, including the design, development, implementation and maintenance of systems, processes and procedures
  • Provide leaders with workforce insights and data to make strategic talent and workforce decisions as well as manage retention and attrition
  • Drive continuous improvement and ensure core HR processes are effectively designed, documented and implemented for sustained and efficient execution; design and implement innovative solutions where applicable

Key Stakeholders:

  • Build strong relationships with cross functional partners to understand business strategy and identify, implement, and manage appropriate solutions
  • Work closely with People Team and Management team on setting strategy, policies and program design
  • Work closely with People Team and managers to plan relevant communication and training

We’d love for you to have:

  • Experience: 10+ years of progressive experience in human resources; 5+ years experience specifically in the design, implementation and management of Total Rewards
  • Experience working in a global company
  • Education: Bachelor’s degree; PHR or SPHR preferred
  • Strong track record in designing and implementing a Global Total Rewards Program
  • Knowledge of U.S. and India employment laws and regulations such as: FLSA, ADA, Wage and Hours, etc.
  • Strong Project Management skills
  • Experience supporting a global workforce
  • Knowledge of best in class web based compensation tools and HRIS systems
  • Strong communication skills (written and verbal); Ability to lead effective conversations with senior stakeholders
  • Ability to analyze statistical/financial data, understand cost impact to business and develop recommendations
  • Ability to prioritize business needs
  • Strong attention to detail and organizational skills
  • Strong verbal and written communication skills
  • Ability to work independently
  • High proficiency in MS Office

Even if you don’t meet all of these qualifications above, we’d still love to hear from you. Tell us about your unique qualifications in your cover letter.

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.