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Leading Through Ambiguity

Senior design and product leaders are rarely asked to solve well-defined problems. More often, the work involves unclear ownership, competing incentives, incomplete data, and real organizational risk. Jessa specializes in helping teams and leaders move forward in these conditions—establishing clarity, decision integrity, and momentum without false certainty.

This work focuses on leadership systems, not artifacts: how decisions are framed, how tradeoffs are made visible, and how teams align when answers are not obvious.

ell a story about your business and let users know more about you.

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Recruit Radar: Designing Hiring Decisions Under Constraint

Context
Field hiring at Walmart involved high volume, distributed teams, and inconsistent systems—forcing recruiters to piece together candidate information across multiple tools. Decision-making was slow, duplicated, and often based on incomplete signals.

The goal was not to redesign hiring screens, but to redesign how hiring decisions were made at scale.​​​​​​​​​​

Leadership Challenge
Recruiting operated under real constraints: offline environments, legacy store systems, and tight operational timelines. The challenge was introducing clarity without adding friction—and ensuring adoption across teams with different definitions of “good hiring.”

What Jessa Led

  • Conducted research to understand how recruiters evaluated candidates in practice

  • Identified duplicated effort and signal gaps across hiring workflows

  • Designed a centralized decision surface that consolidated hiring signals

  • Aligned product, operations, and engineering around feasibility and rollout

Outcome
Recruit Radar reduced duplicate touchpoints, supported offline workflows, and improved the speed and confidence of hiring decisions—demonstrating how design leadership can materially improve operational outcomes in ambiguous, constrained environments.

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InsightHub: Leading Through Data Ambiguity in Enterprise HR Systems

Context
Sam’s Club HR teams relied on fragmented tools and manual processes to access workforce data, creating delays, inconsistencies, and mistrust in decision-making. Leaders lacked a unified view of hiring, performance, and operational metrics across stores and regions.

The opportunity was to design a platform that could consolidate complex HR data into a single, usable system—without oversimplifying the nuance leaders depended on.

Leadership Challenge
The ambiguity wasn’t technical alone. Different stakeholders defined “insight” differently, data sources conflicted, and legacy systems imposed real constraints. The challenge was aligning business, analytics, and design teams around what decisions the platform needed to support—and what clarity actually meant.

What Jessa Led

  • Led cross-functional research to map how HR leaders interpreted and trusted data in real workflows

  • Defined information architecture that balanced standardization with local flexibility

  • Partnered with analytics and engineering to translate raw data into decision-ready signals

  • Designed for both desktop and mobile use in operational environments​​​​​​​​

Outcome
InsightHub unified HR data into a single platform used across Sam’s Club, improving visibility, reducing manual effort, and enabling leaders to make faster, more confident workforce decisions in complex, data-heavy environments.

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