Allison Gregory excels at contracting — and crafting

As the contracts management division chief for Integrated Personnel and Pay System – Army at PEO Enterprise, Allison Gregory is responsible for guiding acquisition strategies that support big-picture goals, making sure the right contracts are in place when they’re needed and ensuring software deliverables are high quality and mission ready. She helps connect leadership priorities with real-world execution and keeps industry partners focused on getting it right.  

Before joining IPPS-A, Gregory spent 15 years with the Army Contracting Command working her way up from contract specialist to contracting officer to branch chief.  

She received her bachelor’s degree in international media studies from Penn State University and a master’s degree in systems and program management from the Naval Postgraduate School. She also was recently awarded a Civilian Service Commendation Medal from the Deputy Assistant Secretary of the Army for Procurement as part of a developmental assignment there. 

Gregory recently shared some highlights from her career and personal life for our Teammate Tuesday series. 

Where did you grow up, and what connection do you still have with that place?  

I grew up in North East, Maryland — yes, that's actually the town's name, not just a vague direction! I spent most of my life there; I even bought my grandfather's house next door to my parents’ place. We renovated it top to bottom but eventually moved to a new location for our children's education. Luckily, I still have tons of family, friends and colleagues there who keep me connected to my roots. 

What do you enjoy doing in your spare time? 

I'm convinced there's no craft project I can't tackle — drawing, painting, embroidery, you name it! Some people even call it my secret supermom power. I live for opportunities to decorate classroom doors, prepare for trunk or treat, or deck out the tables for the swim team banquet. If I can win a competition while doing it — even better! I also dive headfirst into LEGO sets — it's a great way to shut out the noise. When I'm not making a crafting or LEGO mess (apologies to my husband!), I'm usually with my family and our menagerie of pets. We're regulars at our local minor league baseball games, and during the summer, you can find us practically living at the community pool. I volunteer for swim team, wrangling the kids on the ready bench. It's crazy, chaotic and totally rewarding. 

What led you to pursue a career as an Army Civilian? 

The Army Civilian life is a family tradition for me! I'm a proud third-generation member. My grandfather, a World War II veteran, met my grandmother at Aberdeen Proving Ground — she was a secretary, and he was the bus driver who transported her from the train station! He was so smitten that he'd adjust his rearview mirror just to get a better look at her. My dad then spent his career with the Joint Program Executive Office Chemical, Biological, Radiological and Nuclear Defense (then known as JPEO ChemBio), providing our family with a stable and fulfilling life. When I graduated from college, I wasn't sure what career I wanted to pursue, but I knew I wanted the same kind of stability and opportunity for growth that the Army had provided my family for generations. It felt like the perfect place to start my career, knowing I'd have the chance to learn and develop, no matter what role I ended up in. 

Tell us about your developmental assignment at the Deputy Assistant Secretary of the Army for Procurement.  

I'm currently the special assistant to the DASA(P) through a developmental assignment — an opportunity I'm incredibly grateful for, especially given that the offer came the same week as my job offer from PEO Enterprise! Since January, I've gained a unique perspective on Army acquisition during a time of significant leadership and priority shifts. I've been actively involved in reviewing Army contracts to ensure compliance with the new administration's priorities, even leading teams in this effort. This has provided me with a deeper strategic understanding of the importance of aligning contract actions with leadership's goals and maximizing resources to better support the warfighter. It's also been inspiring to meet so many talented individuals dedicated to ensuring our warfighters' needs are met. I'm looking forward to bringing these insights back to PEO Enterprise to help the organization prepare for the changes ahead and continue to effectively support the Army's mission. 

How has Army contracting changed over the course of your career?  

I've had the privilege of witnessing significant changes in Army contracting over the past 15 years. When I started, Army acquisition was heavily focused on developing custom products, often hampered by overly complicated procurement processes that made contracting slow and arduous. We challenged that status quo by pioneering approaches like purchasing professional services at the lowest price technically acceptable and shifting from funding the development of Manpack and Rifleman Radios to purchasing them as non-developmental items — changes that were seen as radical at the time. Of course, change isn't always easy, and we don’t always get it right the first time. But those early challenges actually helped us refine these innovative ideas into best practices. We learned valuable lessons about streamlining technical requirements and focusing evaluations on the true discriminators to identify industry partners best suited to meet the government's needs and accelerate acquisitions. Now, I've seen those lessons become standard practice. The culture has shifted from one rigidly bound by rules to one that actively seeks opportunities to do things faster and better. There's a greater emphasis on finding contractors who truly understand our needs and on implementing contracting processes that facilitate speed and delivery of the best products and services. These changes have prepared us for the accelerated pace we're seeing now. The pendulum is swinging even further, with a strong emphasis on reducing excessive requirements and focusing on acquiring mature commercial capabilities to achieve procurement at the speed of relevance. 

What do you enjoy most about working for PEO Enterprise?  

For me, it's the unique culture at PEO Enterprise that makes it such a rewarding place to work. I'm inspired by the people, the energy and the unwavering commitment to innovation. PEO Enterprise has been a leader in software acquisition for years, and it's exciting to see the organization embrace new challenges and adapt to evolving priorities. I love being part of teams who are not afraid to tackle complex problems head-on, always striving to embrace change while staying focused on the mission. There are so many talented individuals within the PEO who are truly dedicated to meeting the warfighter's needs. Although I'm not co-located with most of the PEO, I recently had the opportunity to attend the PEO Enterprise Summer Ball with my husband, and it was an absolute blast! The Summer Ball really showcased the strong sense of camaraderie at PEO Enterprise — it's clear that people here are passionate about their work and enjoy each other's company. 

What advice would you have for junior Army civilians interested in advancing into leadership roles? 

Leadership isn’t just about stepping up — it’s about paying attention. Listen to the people around you, especially those with different perspectives or quieter voices. Everyone brings something to the table, and good leaders know how to spot that value and connect the dots. Ask questions, stay curious and build strong relationships. Leadership starts when you focus on how to support your team and bring out the best in others — not just when you get a title.