Gartner Expert

Penny Gillespie

VP Analyst

Penny Gillespie is a Vice President and Gartner Fellow in Gartner's Customer Experience/Digital Commerce team which resides in the larger Applications and Software Engineer Leaders Group. Ms. Gillespie is responsible for conducting research and developing publications aimed at helping IT leaders recognize digital opportunities, develop a competitive strategy for digital commerce as well as improve digital commerce performance. She focuses on best practices for personalizing customer experiences and overcoming the hurdles to online selling.

This year she is introducing new research on roguish thinking, a new mindset to enable clients to break down the barriers to idea generation and digital transformation in their organizations. Roguish thinking is an approach to identifying revenue potential. It requires circumventing the status quo, making connections, taking calculated risks and breaking obsolete or counterproductive rules. It identifies seemingly disparate elements that when seamlessly connected lead to revenue maximization.

Previous experience

Prior to joining Gartner in 2012, Ms. Gillespie founded and managed Gillespie International, a consulting service providing insight to clients in the areas of mobile and online commerce, product development, market and product strategy, and financial supply chain automation. Earlier, she covered the e-finance space at Forrester Research and Giga Information Group with a focus on online banking, electronic billing and online payments, as well as mobile payments. She has published more than 225 articles. Over the years, she has held various roles in product and marketing management for such applications as global online banking, U.S. electronic bill presentment aggregation, and multiapplication campus cards, as well as various financial analyst positions for budgeting, loan servicing and real estate management.

She has diverse additional experience: two years as a Senior Product Manager in CyberMark (Sallie Mae subsidiary), four years as a Systems Development Manager/Financial System Analyst/Liaison in Sallie Mae, and nine years as a Real Estate Systems Manager/Analyst/Auditor in JCPenney.

Professional background

Gillespie International

Founder and President

Forrester Research/Giga Information Group

Senior Industry Analyst

Integrion Financial Network/Visa Interactive

Product Manager

Areas of coverage

Digital Commerce Technologies (retired)

CIO Leadership of Innovation, Disruptive Trends and Emerging Practices

CRM Strategy and Customer Experience


M.B.A., The George Washington University

B.S., cum laude, Greensboro College

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Top Issues That I Help Clients Address

1Create a competitive strategy for digital commerce to fuel transformation and revenues.

2Identify new digital opportunities for revenue growth

3Embrace roguish thinking to generate new ideas and facilitate transformation

4Utilize personalization techniques to attract and retain customers

5Evaluate and select vendors for digital commerce platforms.