After the team suffered multiple, simultaneous senior leadership exits in early 2022, Winc had an immediate and urgent need to rebuild the engineering organization’s morale, culture, policies & procedures, management frameworks, and organizational confidence. In addition to key, business-as-usual initiatives needing to be delivered, the technology stack and architecture in place required excessive support and would not economically accommodate the forecasted and needed security, capabilities, & scale of the business.

Brandon immediately prioritized stabilizing team morale and defining core team structures and culture. He then implemented intake, prioritization, and agile frameworks that would produce the necessary data and insights needed to rebuild organizational confidence in the team. This confidence was created by strongly and transparently evangelizing team accomplishments, efficiency, and velocity. Brandon developed and deployed additional key functions such as incident response framework, on-call procedures, testing procedures, deployment procedures, and documentation standards. Brandon also served as a product head/leader to develop and execute against an aligned technology & data roadmap which included a full-stack consultant evaluation, optimizations & cost savings in the current architecture & infrastructure footprint, security optimizations, and major organizational initiatives led by the technology team.

On the data side, Brandon established a data roadmap to drive alignment on core KPI definitions, agreed upon, documented sources of truth, automated data quality checks and alerting on core data pipelines. A thorough and accessible data dictionary, and a clear, organized analytics environment that enables and encourages a citizen-analyst culture were also priorities.

Brandon continuously managed technology & data team budgets against dynamic cash & delivery goals, core business functionality, and future scale. Brandon worked diligently to prevent any opportunity-based or morale-based turnover across both teams.

Pickup was an early stage startup in the last-mile delivery space with no existing data architecture or reporting/analytical capabilities in place. The immediate goal was to collaborate with C-suite and other business leaders to develop a roadmap to support near and long term data needs. As Chief Data Officer, Brandon began by focusing on understanding the business roadmap and building strategic alignment on how the data stack & team would support it. This understanding was then referenced in building a team staffing plan that would be iterated on as the architecture & plan for a budget & time-balanced, scalable modern data stack evolved. As the team and stack took shape, Brandon led the team in developing all new data governance standards, quality checks, alerting, and policies & procedures for intake, prioritization, and communication of deliverables.

After establishing a foundational data & analytics practice, Brandon partnered with senior business leaders to develop and prioritize key analytical initiatives which would provide insights and guidance on how to optimize fundamental business operations. These analyses included a cohort segmentation project to identify key attributes for top performing drivers, then leverage those cohort attributes to drive more effective targeting in the marketing recruitment funnel.

In partnership with AWS, Brandon also worked on a large ML initiative roadmap which would create operationalized models that could predict the likelihood of a failed or delayed delivery based on a score composed of driver attributes, delivery attributes, and route details.