Gail Fierstein

Scaling companies through HR strategies that build leadership strength and transform culture. Advising HR Tech startups on product features and GTM strategy.

Strategic advisor to the CEO and executive team for a retail technology company undergoing rapid scale. Built and led the HR function from the ground up across U.S. and India operations. Scaled global organization from startup to mid-stage by creating end-to-end people infrastructure, performance enablement, compensation, talent acquisition, and manager capability building. Designed a career development framework, improving retention and employee-manager engagement. Built a high-performing People Operations team in India to deliver scalable and standardized processes. Led HR Tech roadmap to unify systems and automate workflows. Extracted the U.S. entity from a PEO and redesigned benefits—boosting employee participation by 10%. CaaStle named a Newsweek Most Loved Workplace in 2024.

SVP HR Business Partner responsible for delivering end-to-end HR: Talent and Leadership Development, Executive Coaching, Compensation, Recruitment, Change management and Organization Design. Designed the new operating model, organization structure, functional capabilities and skills needed to accelerate digital product development.

Sr Director - ReWork America • Responsible for strategic planning, idea development, membership cultivation and project management strategy. Worked with prominent members from technology, academia and public-private organizations on thought leadership, research and policy focused on creating opportunities for Americans to learn and train in innovative ways by seizing the potential of world markets and shared data. • Led the work on the “Employment Triangle” which is the basis for the Skillful, a platform that provides a set of tools that connects job seekers to fast growing, well-paying jobs and to educators who can provide skills development in local communities.

Managing Director – Human Capital Management Directly managed global teams responsible for delivering HR to the business and advancing leadership, talent and culture - Collaborated with a small team of executives to design and implement the HR function of the firm after going public. - Designed and implemented a Talent Framework to cover all aspects of career development including recruiting strategies, career paths and competency definition (specifically for Technology and Operations), training, promotions, diversity and change management. The Talent Framework was tailored for divisional skill sets and workforce strategies. Designed “Management Excellence” competencies as the foundation for management training and accountability used in all divisions. - Developed strategies aimed at increasing senior level diverse talent. Examples of success include increased female MD pipeline in Technology and increased female representation on key business committees. - Oversaw recruiting strategy that resulted in significantly increasing the diverse pipeline recruited from campus, in some cases exceeding the make up of the overall talent pool. - Increased management accountability (MD level) through specific training programs, diversity dialogs, champions and scorecards. Vice President –Technology, NY/Tokyo Designed applications and infrastructure focused on settlements, clearing and overall control framework.