Wesley Johnson

Situation: Peloton partnered with Vitality AIA, a fitness-focused rewards partner in Oceania, to increase member engagement and market presence. The integration required a reliable system to capture member workouts, validate them against strict criteria, and transmit them to Vitality's REST API for points allocation. The system had multiple failure points: invalid account IDs (including accidental Vitality UK entries), API credential expiration, upstream data quality issues, and mismatched workout duration criteria that would disqualify valid workouts.

Task: You were tasked with leading the entire initiative from technical service design through delivery and ongoing support, including orchestration, testing, monitoring, and cross-functional coordination with business, product, and external partners. You also mentored junior engineers through the project.

Action: You designed an end-to-end system using Airflow, dbt, Redshift, and Python that: (1) Ingested workout and account linking data via Python scripts; (2) Defined qualification criteria in dbt models with comprehensive testing; (3) Made near-realtime REST API calls to Vitality's endpoint, capturing every response in S3 and Redshift for audit purposes; (4) Built idempotent, retry-safe pipelines that automatically backfilled unsent workouts after failures without manual intervention; (5) Implemented time-bound entity resolution for many-to-many account mappings; (6) Created a Looker dashboard surfacing every enrolled member's workout with explicit qualification status and reason (too short, unsupported discipline, user not enrolled at time of workout, etc.). During QA, Vitality testers flagged missing points for certain workouts. You analyzed the distribution of actual workout durations across the user base, found that 99.5% of "20-minute" classes ran 18.5+ minutes, and presented data-driven recommendations to relax the qualification threshold. When an upstream system changed discipline labeling from "bike" to "cycling," your dbt test monitoring and Looker health dashboard caught the hard falloff in transmitted events immediately; you updated the model logic and backfilled all unsent workouts in the next cycle.

Result: The system reliably processed 50–200 workouts/day for ~800 enrolled Oceania members without manual intervention, even during upstream outages or API failures. Every member support inquiry could be answered definitively via the audit dashboard. The partnership scaled to represent a meaningful investment play for Peloton's Oceania expansion, and junior engineers on your team learned resiliency and idempotence patterns they could apply to future pipelines.

Situation: You inherited two team members (an analytics engineer and data analyst) from a struggling team that was siloed, missing deadlines (6+ months overdue on a critical refactor), and producing work other teams feared to use. Your existing team of ~5 had built a strong culture of velocity, incremental improvement, and collaborative growth. The inherited team carried tech debt, missed commitments, and low morale. The analyst had been verbally and emotionally abused by her previous leader and was regularly told she was bad at her job.

Task: You were responsible for integrating these two people into your team, unblocking their major deliverable (the refactor), maintaining your team's reputation for meeting quarterly roadmap targets, and ensuring everyone felt valued and developed.

Action: Within 48 hours of the org shift, you conducted listening sessions with the new team members to understand their pain points, pressures, and sense of value. You broke down their hulking deliverables into bite-sized, trackable tickets to create visibility and allow collaboration. You created space for the lead engineer to present his refactored work to the broader team to rebuild trust and credibility. You redistributed business-facing adhoc requests across your team to share the load and model "walking the talk." You leveraged your existing team's "everyone owns everything" culture to get hands-on with the inherited codebase and validate the refactored work.

Result: Delivered a 9-month-overdue refactor in 2 weeks, just in time for a major product launch, unblocking features expected 3-6 months later. The previously abused analyst went on to mentor the more junior analyst on your team and ran point on several major concurrent partnership launches. Maintained team velocity and 3-week schedule buffer through your final two weeks, with team members sustaining performance independently after your departure.

Situation: Four teams (your analytics team, data platform, marketing analytics, and marketing technology) needed to coordinate around repointing an ML model to a new centralized model. The downstream output also needed to be reintegrated into centralized models and served to marketing campaigns. All four individual contributors were competent with skill overlap, but managers were adding redundant voices to coordination meetings.

Task: You needed to decide whether to stay involved in the coordination meetings or step back, and you pushed your managerial peers to do the same.

Action: You recognized that the ICs had high skill overlap, low context overlap, clear deliverables, existing rapport with each other, and mature operating styles. You opted out of the coordination meetings entirely, removing managerial friction from the process and trusting the ICs to self-organize.

Result: The project was completed in less than 2 business days, versus the original 2-week estimate from managers. This unclogged development pipelines and became a story demonstrating how quickly the organization could move when cutting redundant managerial friction.

Situation: Wesley was brought in as a solo hybrid engineer/manager to serve 5 senior leaders across Peloton's critical revenue-generating verticals (1P Retail, 3P Retail, Strategic Partnerships, Commercial, International). He was responsible for reconciling vastly different stakeholder needs while his VP stepped away to focus on Finance. This created a bottleneck: one person handling all technical delivery, stakeholder management, and strategic planning.

Task: As the team grew to 7 people, Wesley needed to deliberately distribute his work, relationships, and technical ownership without losing quality or stakeholder trust. He had to match each team member to the right vertical, product, or stakeholder relationship based on their strengths and growth potential — all while expanding coverage from 5 to 30+ senior leaders.

Action: Wesley took a strategic, phased approach to delegation:

Result: The team scaled from 1 to 7 people while stakeholder coverage expanded from 5 to 30+ senior leaders. Roadmap delivery remained consistently high (as promised from day 1), but the scope and breadth of projects grew exponentially. Adhoc request cycle time improved dramatically: from 2-week delays when solo, to <1 day 70% of the time and <2 days 90% of the time by the end. Wesley was known for exceptionally strong stakeholder relationships compared to peers. Three team members were promoted: two Sr AEs to Staff AE, and one Analyst to Sr Analyst. The team operated with high autonomy and continued to deliver impact after Wesley transitioned out, demonstrating a sustainable, scalable organization.

Situation: Peloton's data organization was a patchwork of merged teams with siloed domains. The dbt data warehouse had ~1.5k models organized in separate lineage graphs with high redundancy, undocumented assumptions, and tangled Airflow DAGs. Teams rarely collaborated—engineers said "I don't want to bother them"—and lateral visibility was near zero. The organization was experiencing 2-3 tier 1 Airflow failures (on-call incidents) per week.

Task: You were responsible for creating visibility, breaking down silos, establishing technical standards, and improving operational reliability across a ~30-person distributed data department while enabling engineers to collaborate and reduce duplicate work.

Action: You designed a dual-track design review process: (1) Weekly "showcase" sessions (a hard gate for project development, attended by VP and ~30 people) where engineers presented work across models, dashboards, and exploratory analyses—creating cross-team visibility and engagement; (2) Biweekly roundtable with analytics engineers to discuss standards, friction points, and technical decisions. The roundtable produced formal documentation for model layering, naming conventions, orchestration, testing, and refresh strategies. You owned the showcase agenda, drove participation, and integrated it with broader initiatives (Tech Debt Extravaganzas, EDA Days). You also implemented lineage testing via dbt integrated into a containerized development environment to prevent future redundancy.

Result: Over 14 months, tier 1 Airflow failures dropped from 2-3/week to 1 every 3-4 weeks. Eliminated ~200 redundant models out of 1.5k (~13% deduplication). Models showed tighter testing, better documentation, and faster iteration cycles. Cross-team collaboration emerged (e.g., co-hosted user model refactor presentation). Automated lineage testing prevented future recurrence. Process was handed to Senior Director and continued to evolve after your departure.

Situation: You inherited two team members (an analytics engineer and data analyst) from a struggling team that was siloed, missing deadlines (6+ months overdue on a critical refactor), and producing work other teams feared to use. Your existing team of ~5 had built a strong culture of velocity, incremental improvement, and collaborative growth. The inherited team carried tech debt, missed commitments, and low morale.

Task: You were responsible for integrating these two people into your team, unblocking their major deliverable (the refactor), and maintaining your team's reputation for meeting quarterly roadmap targets while ensuring everyone felt valued and developed.

Action: Within 48 hours, you conducted listening sessions with the new team members to understand their pain points, pressures, and sense of value. You then broke down their hulking deliverables into bite-sized, trackable tickets to create visibility and allow collaboration. You created space for the lead engineer to present his refactored work to the broader team (rebuilding trust and credibility). You redistributed business-facing adhoc requests across your team to share the load and model "walking the talk." You leveraged your existing team's "everyone owns everything" culture to get hands-on with the inherited codebase.

Result: Delivered a 9-month-overdue refactor in 2 weeks, just in time for a major product launch, unblocking features expected 3-6 months later. Maintained team velocity and 3-week schedule buffer through your final two weeks, with team members sustaining performance independently after your departure.

Situation: The candidate was responsible for acquisition-side executive reporting displayed in Tableau and fed through a SQL Server on-prem instance. The organization had multiple data professionals at varying skill levels who needed guidance on how to leverage Tableau and navigate the data warehouse. There was no standardized approach to building dashboards or training analysts.

Task: The candidate needed to serve as Tableau server admin, ensure system stability, and train an array of data professionals across the company on how to effectively use Tableau for their analytics needs while guiding them through the data warehouse structure.

Action: The candidate built parameterized dashboards with controls for frequently-asked-about attributes, making it easy for stakeholders to self-serve and explore variations without requiring custom queries. They conducted office hours with data professionals across the company, providing hands-on coaching and guidance. They documented and shared historical knowledge about the data warehouse structure and best practices. They maintained Tableau server stability and performance while scaling the platform to support more users and use cases.

Result: Tableau became the standardized tool for executive reporting across the organization. Data professionals gained confidence in using Tableau and the data warehouse independently. The candidate's parameterized dashboards reduced ad-hoc request volume and enabled faster decision-making. The organization developed a more data-literate workforce with consistent standards for analytics and reporting.

Situation: The candidate was tasked with building end-to-end customer onboarding data models from lead capture through first billing. The sales order model proved to be the most complex component because orders could be edited at any point in time—customers could add or remove line items, change payment methods, or modify quantities. This created significant challenges for both accounting reconciliation and forecasting accuracy, as the same order could have different contents when viewed at different points in time.

Task: The candidate needed to design a data model that could handle late-arriving facts and order mutations while providing both sales leadership with a consistent snapshot for forecasting and accounting teams with a complete audit trail for reconciliation.

Action: The candidate created a solution that functionally snapshotted orders based on criteria that couldn't change, while maintaining separate late-arriving facts for accounting reconciliation. They identified immutable qualifying events and status-change gates that would define when an order was "complete" for forecasting purposes. They then built dashboards showing both metrics side-by-side, with candlestick charts that categorized and explained the differences between the two definitions over time. The candidate conducted extensive training and explanation to get stakeholders on board with the different definitions and the reasoning behind them.

Result: The model successfully handled order mutations and late-arriving facts, enabling accurate forecasting while maintaining accounting reconciliation. Sales leadership and accounting teams gained confidence in the data. The candidate earned significant trust from senior leadership across the company through their ability to solve a complex technical problem that had business-wide implications. Connecting lead records to orders to customer records became straightforward once the foundational order model was established.

Situation: While building customer onboarding forecasting models, the candidate discovered that Accounting and Sales teams had been using conflicting sales definitions for years without reconciliation. Numbers shifted unexpectedly, threatening forecast credibility. Multiple stakeholders across the organization were pulling the same metric in different directions, and the CMO struggled to explain the sales definition during an executive boardroom meeting focused on funnel diagnosis.

Task: The candidate needed to identify the root cause of the sales definition discrepancy, build a solution that both teams could trust, and present findings to executive leadership (COO, CEO, CMO, Sales VPs) in a high-stakes boardroom setting to align the entire organization on a single definition.

Action: The candidate diagnosed the problem by connecting with stakeholders adjacent to the customer onboarding process and learning how each was interpreting "sale" differently. They took ownership of tracking down why numbers shifted and getting everyone aligned. They built Tableau dashboards specifically designed to compare variations in sales definition criteria, including parameters and controls for hot-button attributes that stakeholders frequently questioned. When called into the executive boardroom, they used Tableau to live-filter and show the deltas, demonstrating how shifting sales dates by a few days based on different criteria could drastically impact budget attainment, forecasts, and quotas. They also created candlestick charts to visualize and categorize reconciliation differences between the two definitions.

Result: Executive leadership gained clarity on sales definition impact and shifted from skepticism to trust. The sales team stopped pushing back against the candidate's analyses and recognized they could rely on the candidate to explain any future deltas. The candidate was given increased authority in sales team training and moved from being seen as a critic of sales methodology to being a trusted technical advisor endorsed by senior leadership. The organization achieved alignment on sales definitions, enabling reliable forecasting and accounting reconciliation.