Fixing the System, Not Just the Output

Summary

I joined Diligent in August 2024 to lead and scale design during a period of growth, but quickly realized the biggest constraint wasn’t talent or effort — it was organizational structure.

With limited historical context, no additional headcount, and a system I didn’t design, my responsibility was to assess what was working, correct what wasn’t, and do so with restraint, logic, and empathy.

These changes needed to happen quickly and with minimal disruption. I wasn’t hired to reshuffle design leaders, but to improve design’s impact across Diligent’s product portfolio.

This case study focuses on how I diagnosed structural issues, made uncomfortable but necessary changes, and rebuilt a healthier design organization designed to scale that began rolling out in January 2025.

TL;DR: My Decisions

• Exits: I made the call to exit four leaders to redistribute management scope.

• Additions: I've since created an additional Director role that oversees teams that were originally distributed across different leaders, hired new external leaders to uplevel craft and quality at sclae, and added new Senior Design Manager and Manager roles, and introduced a Manager Apprentice role to give current IC designers a safe approach to learning if management is right for their career path.

• Promotions: As a result of more explicit promotion criteria and performance expectations, there were 7 promotions into leadership or senior roles to meet the demands of the work.

Context

When I joined Diligent, there had been very little intentional organizational design within the design function. Reporting structures had evolved organically over time, likely shaped by growth, tenure, and local optimization rather than deliberate planning.

The result was extreme inconsistency in scope, spans, layers, and where valuable dollars were allocated.

Individually, these roles were filled by capable, well-intentioned people. Systemically, the structure was broken.

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Why the Status Quo Wasn’t Neutral

The effects of this structure were visible across the organization:

• Quality suffered. Work shipped without critique, not because standards were low, but because managers were too overloaded to create or participate in meaningful review rituals.
• Process collapsed under load. Managers spent their time talking about work in meetings instead of shaping it with their teams.
• Investment was misaligned with impact. A disproportionate amount of budget was tied up in roles that weren’t directly improving product outcomes — an imbalance I often described as allocating most of the salary cap to positions that couldn’t move the game forward.
• Ownership was unclear. Reporting lines and scopes of responsibility didn’t make sense to leaders or individual contributors, making accountability and growth opaque.

This wasn’t a people problem. It was a systems problem — and left unaddressed, it would continue to erode morale, trust, and product quality.

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Constraints That Shaped My Approach

I didn’t have the luxury of a clean slate.

• There was no additional headcount budget. Any leadership changes had to be self-funded.
• I had limited data about how the structure came to be, only its present-day consequences.
• Any changes would affect real people who had been doing their best within a flawed system.

This meant the work required judgment, sequencing, and care — not speed for speed’s sake.

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How I Diagnosed the Problem

Rather than start with titles or org charts, I focused on patterns:

• Management span relative to the ability to assure quality
• Clarity (or lack thereof) in decision ownership
• Where time was actually being spent versus where impact was expected
• Whether the structure would make sense to someone joining the company for the first time

The conclusion became unavoidable: these issues could not be solved through coaching, patience, or incremental tweaks. The structure itself was preventing people from doing good work.

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Principles That Guided the Redesign

Once it was clear change was necessary, I anchored on a few core principles:

• Be deliberate where decisions were irreversible; experiment where they weren’t.
• Make changes meaningful enough to signal seriousness, both to senior leadership and to the design organization.
• Optimize for long-term scalability, not short-term band-aids.
• Sequence ambition responsibly. In several cases, I hired directors into roles that would eventually need to become senior director or VP-level positions, with the intention to evolve them as the organization matured.

Restraint was as important as decisiveness.

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What Changed

The redesign focused on restoring coherence:

• Leadership scope was normalized to allow for real people management, critique, and quality ownership.
• Reporting lines were clarified so that accountability and growth paths were understandable.
• Management layers were introduced where junior teams needed support, direction, and advocacy.
• Leadership roles were redefined around impact and responsibility rather than tenure or legacy scope.

Throughout this process, empathy showed up operationally:

• Business unit leaders and HR partners were brought into the thinking early.
• Communication was fact-based, neutral, and transparent.
• I owned the hardest conversations personally rather than delegating them away.

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Signals the Structure Was Healthier

Before any formal metrics caught up, the signals were clear:

• Designers and leaders with experience at other companies recognized familiar, healthy patterns in the new structure.
• The organization made sense to outsiders and insiders alike.
• Peer leaders and executives expressed confidence in the leadership team being put in place.
• New leaders independently introduced operating rhythms — quality critiques, monthly executive updates, and new ways of thinking — without being directed to do so.

The system was starting to work on its own.

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What This Taught Me About VP-Level Leadership

I believe VPs of Design are hired to quickly assess what’s working and what isn’t, and to stay grounded in why they were brought in — whether to fix the organization, fix the product, or steward both.

The role requires judgment more than certainty: balancing what can be proven with data against what is clearly visible, even when evidence is correlated rather than causal. It also requires sequencing — understanding what’s possible now, what must wait, and how to change the status quo without breaking trust or momentum.

This work was uncomfortable at times, but necessary. And it reinforced a core belief I carry forward: design leaders aren’t just responsible for what teams ship — they’re responsible for the systems that make good work possible.