Hillery Simmons is a seasoned executive and transformative leader with over two decades of experience driving data and analytics strategy across technology, retail, and e-commerce sectors. With a strong foundation in mechanical engineering and an MBA from DePaul University’s Kellstadt Graduate School of Business, Hillery blends technical acumen with strategic business insight to deliver innovative solutions that enhance performance, customer experience, and organizational growth.
Currently serving as Vice President of Analytics at Stylitics, Hillery leads the company’s reporting and optimization strategy. She is responsible for defining the value of Stylitics’ products through data and analytics, managing the roadmap for client reporting capabilities, and executing a rigorous testing and optimization program that informs product development and delivers increasing value to Stylitics’ retailer partners. Under her leadership, Stylitics successfully launched a high-impact core reporting suite, an embedded client reporting platform, and a scalable data quality management solution—all critical components that foster trust and transparency with clients and internal stakeholders alike.
Prior to Stylitics, Hillery served as Vice President of Enterprise Analytics at Tailored Brands, where she oversaw a wide range of analytics functions, including machine learning, A/B testing, business intelligence, and customer insights. She implemented a Media Mix Model, a retail testing platform, and an app analytics program, delivering needed analytics capabilities to support the business strategy. And she played a critical role in macroeconomic forecasting, helping leadership navigate a rapidly changing retail landscape.
Hillery’s impact was particularly notable during her five-year tenure as Vice President of Analytics at ShopRunner. There she led the transformation of data and analytics into a strategic asset that enabled smarter decision-making and accelerated business growth. She built a centralized analytics organization that partnered closely with functional leaders across marketing, finance, and operations to define performance metrics, deliver insights into customer and partner behavior, and identify key drivers of growth. She established a dedicated product analytics team that worked collaboratively with engineering and product management to instrument digital experiences, analyze user behavior, and shape product roadmaps. And to support scalability and governance, she implemented a modern analytics platform—integrating a centralized data warehouse, self-service BI tools, and automated data pipelines – that fostered data literacy within the organization and ensured data was trusted, accessible and actionable.
Earlier in her career, Hillery held leadership roles at Orbitz, where she launched a new analytics function supporting product and customer service teams and spearheaded a priority error reduction program that achieved an 8% improvement in key metrics. She also served as Director of Business Operations at Silicon Valley Data Science and spent over a decade at Accenture in roles of increasing responsibility, including Business Operations Lead for Accenture Technology Labs and Project Manager for R&D prototype development. During this time, she was named a co-inventor on two U.S. patents, highlighting her early commitment to innovation.
Throughout her career, Hillery has consistently built and led high-performing teams, growing organizations from small, specialized groups into scaled functions with broad business impact. Known for her collaborative leadership style, she excels at working cross-functionally to build trust, influence stakeholders, and drive alignment around data-informed strategies.
Hillery holds an Executive Data Science Certificate from Johns Hopkins University via Coursera and is a member of Beta Gamma Sigma. Her technical toolkit includes expertise in modern BI tools and platforms such as Looker, Tableau, and Amplitude, alongside deep proficiency in SQL-based systems, A/B testing, cloud architectures, and data governance.
Passionate about developing talent and building a data-driven culture, Hillery is now exploring opportunities to bring her insights and leadership to advisory and board roles. She is particularly drawn to organizations undergoing transformation, seeking to scale, or looking to harness the power of analytics to unlock new value.
Combining a sharp analytical mind with creative problem-solving and a strong sense of mission, Hillery Simmons is a dynamic leader who empowers teams, strengthens strategy, and builds the data foundations that enable companies to grow with confidence.
Character: Hillery Simmons is a trusted, collaborative leader known for her integrity, resilience, and ability to build high-performing teams in dynamic environments.
Knowledge: With deep expertise in analytics, data strategy, and product optimization, Hillery brings over 20 years of experience across technology, retail, and e-commerce sectors.
Strategic: She excels at aligning data-driven insights with business goals, driving innovation and long-term value through well-executed, measurable strategies.
Communication: Hillery is a clear and compelling communicator who translates complex data into actionable insights, earning buy-in from stakeholders at all levels.
