Operations · Programs · Implementation · Learning

I make complex work navigable.

I get close enough to day-to-day work to understand where reality breaks from the intended process, then zoom out far enough to redesign the structure around it.

Chicago-based · Open to mission-driven work

Selected work

Transformation at two very different scales.

01 · Flagship case

Rebuilding a workforce program around the participant journey

A compliance recovery became a deeper operational transformation connecting program delivery, participant information, staff ownership, evidence, and state requirements around one shared lifecycle.

38→87→96%Compliance recovery and redesigned cohort
20→65Monthly program inquiries
~600Inquiries brought into one pipeline
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02 · Major case

Building the operating model while Amazon Fresh was still becoming one

In an emerging business scaling nationally, live-store experience became launch infrastructure, workforce-readiness models, national learning programs, operating standards, and reusable knowledge.

57Stores in the implementation network
7New-store launches supported
34SOPs and best practices authored or shaped
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How I work

Curiosity tends to become structure.

I rarely begin with a tool or an inherited explanation. I begin by understanding what people are trying to accomplish, how information moves, what the requirements demand, and where the actual work no longer matches the assumed model. The value is not simply what gets built; it is the investigation that makes the right response possible.

See the approach
01Follow the evidence

Investigate requirements, source material, data, handoffs, and the people closest to the work.

02Find the structure beneath it

Surface dependencies, ownership, information flow, failure points, and human consequences.

03Make it usable

Turn learning into workflows, programs, tools, controls, documentation, and shared capability.

What colleagues say

“Kendra asked the questions others didn’t, dug into the details, and wasn’t afraid to challenge an idea when she saw a better way forward. She could move between data, problem solving, and facilitating with leaders while still bringing energy and personality to the team. Kendra made the work better and the team better, and I’d gladly work with her again.”
David DownerFormer Field Learning Program Manager, Amazon Fresh
“Kendra consistently demonstrated strong leadership, sound judgment, and a high level of accountability. Her natural aptitude for leadership, combined with her ability to quickly assess situations, solve problems, and effectively lead others, gave me the confidence to entrust her with stretch assignments and responsibilities beyond her own role. She consistently demonstrated the ability to take on greater challenges, deliver results, and positively influence those around her.”
Edward HensleyFormer District Manager, Marshalls

About Kendra

Good operations should not make an organization feel less human.

My career has moved across retail operations, workforce leadership, new-store launches, national learning programs, technology implementation, and mission-driven program operations. The environments look different, but the operating instinct has remained consistent: get close enough to understand the real work, then build structure that reduces friction, protects people from preventable failure, and preserves room for human judgment and relationships.

Possibility catches my eye, especially the kind that isn’t obvious at first. I see potential in furniture left in an alley, one thriving plant that could become fifteen more, or a recipe that makes me wonder what would happen if I changed the method.

More about Kendra
Portrait of Kendra Toomey

What comes next

I am interested in work where the objective matters, the environment is complex, and the path forward still needs to be understood.

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