I built a strategy so precise it aligned executives, impressed Deloitte, and gave a fractured team something to stand on together — by designing around the culture, not against it
A long-horizon enterprise strategy built through political complexity, cultural diagnosis, and intentional partnership — that earned VP endorsement, shaped Deloitte's RFP process, and produced tools that outlasted the effort itself.
The E2E Outbound Gigamap — one of two system-wide visualizations built for Enterprise Transportation (inbound and outbound). This one maps outbound transportation flow, friction points, and critical pairings. Deloitte used it to build TMS RFP requirements. 84.51 used it to identify scalability barriers. Teams used it to onboard new members.
When I arrived, competing priorities displaced each other in rapid rotation.
The team had no long-horizon alignment. Product decisions were driven by gut instinct and whoever had the loudest voice that week.
The chaos had a second layer I could feel but took time to name. This was a deeply Midwestern operating culture — indirect communication, persistent pleasantness, a reflexive conflict avoidance that made honest conversation nearly impossible. Problems didn't surface cleanly. They circulated beneath a permanent cloak of "everything is fine" until they became something bigger. Two years of attempts to lead a strategy process were systematically thwarted — not through open resistance, but through the slow, quiet maneuvering of a team that had learned to protect itself by prolonging ambiguity.
Without a coherent strategy, $24 million in annual transportation technology investment had no rudder. The cost wasn't just misaligned capital — it was a function that could not demonstrate its own direction or value to the executives asking for both. What it needed was not another attempt at a strategy. It needed a process designed to succeed inside the culture that had defeated every previous attempt.
I diagnosed the culture before I designed anything.
Most people try to manage difficult personalities. I assess the culture producing them — and that's a fundamentally different diagnosis.
This is the work of a service designer applied to a human system. Most people enter a difficult environment and try to manage the personalities. I entered and assessed the culture producing those personalities — the Midwestern operating norms, the conflict avoidance baked into every interaction, the way pleasantness functioned as a shield rather than a signal. Once I understood what I was actually dealing with, I could design around it precisely instead of reacting to it repeatedly.
I'm a direct communicator, shaped by years in California and Washington DC. When I assessed this environment — built on indirect communication, persistent pleasantness, and reflexive conflict avoidance — I didn't try to pretzel myself into someone I wasn't. I identified what the work needed and found the right instrument for each part of it.
What I brought was strategy rigor: the MBA, fifteen years of experience creating strategy, the methodological discipline to hold a sequential process steady under pressure. What the environment also needed was someone who could navigate it on its own terms — trusted, patient, indirect where required. I brought Howard. In service design, everything is intentional because everything is impactful.
Rather than starting from scratch, I built on the existing Supply Chain Strategy authored by one of my key business partners. I invited him to present his strategy directly to our team — a significant move given that the team didn't like him. What that invitation modeled was alignment and partnership rather than competition. It reframed the transportation team from a siloed group into contributors to something larger.
When I arrived, product and business teams weren't just misaligned — they were actively at war. No shared language, no shared direction, no functional relationship between the people building the technology and the people whose operations depended on it. I built the bridge: shared artifacts, shared vocabulary, shared accountability. The alignment this produced wasn't a soft outcome. It was the precondition for the TMS/WMS modernization that followed.
The first two attempts were thwarted — not through open resistance, but through quiet maneuvering by a team that had learned to protect itself by prolonging ambiguity. This time we changed the conditions. Two large kickoffs with the full team, then daily 3:1 and 4:1 working sessions for six months. Howard ran parallel 1:1s, validating and keeping people tethered. I held the synthesis and analytical rigor steady through every challenge.
Everyone got a sense of contribution and ownership. Nobody had grounds to reject work they'd been part of building. The result: a team that co-owned a strategy they had tried to prevent for two years, a VP presentation that earned immediate endorsement from every KTD executive in the room, and external adoption by Deloitte and 84.51.
Not a slide deck. A complete operating system — for the strategy and for the team running it.
Ways of Working
Before the strategy could be built, the conditions for building it had to exist. I designed the engagement structure — workshop cadences, 1:1 formats, contribution frameworks — so that a politically resistant, conflict-avoidant team could participate productively without feeling exposed. The process was the first deliverable.
The Strategy — 15+ Elements
Mission. Vision. Four strategic pillars. User groups and value propositions. A strategy scorecard with three measurement levels. A tech & BI maturity model. Initiative detail and stakeholder tool. Build/buy decision framework. Two gigamaps — inbound and outbound. A grounding alignment to the wider Supply Chain Strategy. This is not a deck. It is a system.
Evangelization + Roadshow
I urged Howard to roadshow the strategy rather than publish it. We presented to the VP of KTD, then to all KTD executives. Both sessions landed immediately. Executives endorsed it, asked us to expand it, and invited further collaboration — before the lead product designer attempted to commandeer that process and was outed as the source of ongoing obstruction.
The Bridge I Built — Product Teams + Business Teams
When I arrived, the product and business teams were not misaligned — they were actively at war. There was no shared language, no shared direction, no functional working relationship between the people building the technology and the people whose operations depended on it. I built the bridge: inviting my Supply Chain partner and the existing Supply Chain Strategy into the room, grounding every product decision in a business question, and creating the connective tissue — shared artifacts, shared vocabulary, shared accountability — that made modernization possible. The alignment this produced wasn't a soft outcome. It was the precondition for everything that came next.
Good strategy doesn't begin with people declaring what it should be. It begins with rigorous inquiry — allowing the strategy pillars to reveal themselves.
The strategic pillars for Enterprise Transportation weren't chosen in a room by people with opinions. They were surfaced through a structured process: workshops with seven cross-functional groups, secondary research, user feedback, systems analysis, and iterative critical thinking across six months.
What emerged were themes that kept reappearing regardless of who was in the room or what role they held — frictions, gaps, and opportunities that the system itself was pointing to. The pillars didn't come from the team's preferences. They came from the evidence. That distinction matters because it's the difference between a strategy people defend and a strategy people trust.
The same process surfaced the vision — "Frictionless flow from farm to fork" — and the mission. These weren't phrases invented in a naming session. They were the natural language of what the data was already saying.
Roadshowed to the VP of KTD, who loved it immediately. All KTD executives endorsed it and asked the team to build further — the first unified strategic direction the function had ever had.
Deloitte used the gigamap to develop TMS RFP requirements. 84.51's Director of Product told other teams: "How you work is the example we have given to the merchandising team of what we need to be successful."
The annual transportation technology investment had no strategic alignment before this work. The strategy gave that capital a direction — and gave leadership the framework to evaluate whether the investment was moving the organization forward.
Zero waiting. Zero waste. Zero hassle. — the singular phrase that gave a fractured team something to stand on together.
"How you work is the example we have given to the merchandising team — of what we need to be successful."
84.51 Director of Product · Supply Chain"From a technical and solution architecture perspective it's extremely helpful — it gives a high head start on any design discussion."
Deloitte Team · Referencing the Gigamap"Thanks for walking us through this ginormous map and making the complex make sense."
Dev Ops TeamThe tools that turned a strategy into something executable.
E2E Gigamaps — Inbound + Outbound — Two system-wide maps of flow, friction, and critical pairings across the full transportation network. Used by Deloitte for TMS RFP requirements, by 84.51 to identify AI scalability barriers, and by teams to onboard new members.
Strategy Scorecard & Execution Toolbox — A three-level measurement framework (Business, Strategy, Product) paired with a tech maturity model, initiative stakeholder tool, and build/buy decision framework. Built to run the strategy without a guide.
This project is proof that service design is not about deliverables — it's about reading systems, including the human ones. Layer 2 (Harmonization) happened through cultural diagnosis; Layer 3 (Service Scaffolding) happened in the tools: the gigamaps, the scorecard, and the execution frameworks that made the strategy operational and durable.
How I Work →The product-business alignment built here became the foundation for the next chapter: TMS/WMS Modernization — the enterprise technology overhaul that the strategy had identified as the single highest-leverage investment in transportation's future.
See that project →