Case Studies

Case Study 1: Twitter

Turning Day-0 Onboarding from Manual Chaos into a Scalable, Audit-Ready System

Role: Senior Technical Solutions Engineer, Lead
Team: Led an internal engineering team of 8, partnering cross-functionally with onboarding, IT, and internal security stakeholders.

  • Twitter was onboarding 40–60 new employees per week, but endpoint management and imaging workflows were manual and inefficient. Preparing devices and access for weekly cohorts took dozens of hours of repeated work, and the process lacked consistency and quality assurance. The result was predictable: high-capability people were spending their time on repetitive tasks instead of engineering improvements, and the onboarding experience was exposed to preventable errors. At the same time, endpoint systems needed to stay secure and aligned with internal security requirements and audit readiness.

  • The work wasn’t failing because people weren’t trying. It was failing because the system was under-designed:

    • Critical steps lived in tribal knowledge rather than repeatable processes.

    • Manual workflows created variability and rework.

    • The team was trapped in urgent operations, leaving little time for improvement.

    • “Perfection” expectations risked driving analysis paralysis instead of iterative delivery.

  • I led the turnaround by combining systems thinking, practical engineering, and cross-functional alignment.

    1) Start with deep discovery, not assumptions
    In the first weeks, I interviewed and shadowed stakeholders to understand what each group thought their role was, what they were actually doing, and where the pain lived in the real workflow.

    2) Remove the biggest constraint first (automation + QA)
    I identified a lengthy manual workflow as the highest-leverage bottleneck and built an internal tool to automate it, reducing work from hours to minutes while adding a built-in quality assurance layer. This reclaimed significant time and made outcomes more consistent.

    3) Drive adoption through enablement, not mandates
    Tools don’t change systems, people do. I trained the relevant teams on the new process, explicitly connecting it to outcomes they cared about: (a) a better new hire experience and (b) less manual toil, more time for meaningful work.

    4) Create cross-functional alignment mechanisms
    To prevent silo drift, I implemented cross-functional lunch-and-learns so teams could see upstream/downstream dependencies, share context, and identify opportunities to cascade or combine work. Later, I added technical cross-training to raise org capability and resilience.

  • The shift wasn’t just building a tool, it was changing the operating system.

    • Improved Day-0 readiness: a higher percentage of employees were productive on arrival.

    • Increased velocity: less time lost to manual labor, more focus on projects and improvements.

    • Fewer onboarding issues: quality assurance reduced preventable new-hire friction.

    • Sustained adoption: years later, colleagues reported that tooling and testing matrices I created were still in use.

  • In a 1:1, a leader told me they were looking for “perfection.” That became a defining moment in how I lead.

    Perfection is abstract and ambiguous. It’s impossible to measure in a way that enables learning. It can unintentionally reduce psychological safety, increase risk aversion, and create analysis paralysis. At Twitter, that cut against a core value: “Ship It.”

    My takeaway: don’t impose perfection as the standard. Instead:

    • Experiment safely

    • Learn blamelessly

    • Iterate visibly

    • Improve continuously

    Perfection, in practice, is the accumulated result of many small improvements, so we focus on doing the next right thing, learning quickly, and making the system better over time.

  • This experience directly shaped the competencies and tools I teach in Leadership Bootcamp:

    • Navigating complexity and ambiguity (diagnose the system; reduce uncertainty through experiments)

    • Agile learning (iterate safely; build feedback into the work)

    • Leading with self-awareness (recognize how standards and language affect safety and outcomes)

    • Results architecture (remove constraints; design workflows for predictability and scale)

    • Coaching for the next generation (cross-training; building capability beyond the leader)

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Case Study 2: Tinder

Building a lean global technical operations org that scaled with growth and developed talent

Role: Senior Manager, Information Technology and Operations
Team: Started as a team of 2 (manager + technician) and grew into a multidisciplinary unit covering global technical operations: network, audiovisual, new office builds, endpoint engineering/automation, and cloud productivity infrastructure.

  • Tinder’s global workforce and technological demands were growing quickly, while the IT/operations function needed to remain lean and high-performing. Symptoms showed up in familiar ways: expanding office footprint across locations, increasing headcount, rising hardware and vendor spend, and distributed teams feeling disconnected.

    At the same time, the function carried high-stakes responsibilities: Day 1 onboarding productivity, endpoint security, successful IT SOC audits, a multimillion-dollar budget, new office builds to spec, vendor negotiations, and reliable AV + network infrastructure across offices and meeting spaces.

  • The core question wasn’t “How do we do more work?” It was: “How do we maximize performance and capability as demands scale, without burning people out?”

    • The team needed clarity on what the job truly required (and which work was routine vs high-leverage).

    • Cost and inventory visibility was a prerequisite for controlling spend.

    • Internal customers needed to feel supported regardless of location.

    • Repeatable requests had to be redesigned for self-serve and automation.

    • Capability building had to be deliberate, measurable, and career-expanding.

  • I built the function by combining operating-system design, customer discovery, and deliberate talent development.

    1) Take stock of the work and remove ambiguity
    I started by understanding what the existing technician was doing day-to-day and whether the work was solving real problems or simply maintaining the status quo.

    2) Establish inventory and spend control as a foundation
    We introduced inventory management and endpoint management to track and trace purchases immediately. In parallel, I brought in a channel partner to unlock volume discounts, shifting procurement away from direct manufacturer purchases where it made sense.

    3) Listen to the customer across the company
    I met with employees in every department to understand what was working, what wasn’t, and where friction was costing time and energy.

    4) Install an operating rhythm that scales
    I implemented a daily, time-boxed stand-up (3 minutes per person: what’s working, what’s not, what’s blocked) and weekly 1:1s. As the team grew, this cadence became the backbone of alignment, accountability, and fast unblocking. I also implemented lunch-and-learns and regular stakeholder cadences with leaders across the company.

    5) Systematize support with an “Empower the User” strategy
    We built extensive documentation and self-serve workflows to offload repeatable requests in a way that felt supportive, not dismissive. We paired this with a “walk-up” policy and a single Slack pathway to help, so distributed colleagues could get support immediately without ticket overhead.

    6) Build automation and reduce manual toil
    We built internal tools for onboarding and offboarding that nearly eliminated manual intervention, reclaiming time for higher-value work.

    7) Develop talent with a curriculum, not ad hoc training
    I created a year-long “Level Up Curriculum” using the books Python Crash Course and Pro Git, with weekly/monthly/quarterly milestones. The goal was practical: build automation capability, increase technical fluency, and enable stronger collaboration with engineers. The result was real career mobility: one team member moved into a senior site reliability engineer role and another into a software engineering role.

    8) Protect energy with a structured 4-day workweek trial
    Once the team was operating smoothly, I implemented a 4-day workweek as a 90-day trial with guardrails: staggered days off, SME escalation coverage, and cross-training backups. I worked five days per week to backstop coverage and model support for the team.

  • The combined effect was a lean function that scaled its impac and improved quality of life.

    • Increased capability and throughput while remaining lean, supported by clear cadences and role clarity.

    • Improved morale and performance during the 4-day workweek trial (standard-length days, not compressed 10-hour shifts).

    • Stronger distributed-team connection through state-of-the-art conference room AV that made remote collaboration feel co-located.

    • Durable systems: documentation, self-serve pathways, and automation workflows became the standard operating model.

    • Talent outcomes: measurable upskilling and internal mobility into SRE and software engineering roles.

  • During a corrective feedback conversation with a direct report in an open floor-plan area, he asked to move into a conference room. He gave me immediate feedback that he didn’t appreciate being corrected in that tone in front of others. I took it seriously, and I never forgot it.

    That moment reinforced a simple principle: praise in public, admonish in private. It made me a better coach, improved trust, and helped me handle performance moments with more respect and effectiveness.

    It also reinforced another belief that shaped my leadership and the genesis of Leadership Bootcamp: real development requires curriculum, practice, and transfer, not one-off lectures or assignments. When you combine clear expectations, repeatable practice, and psychological safety, people grow fast.

  • This experience directly shaped the competencies and tools I teach in Leadership Bootcamp:

    • Valuing diversity in daily work

    • The Global Navigator

    • The Results Architect

    • Mastering Productive Conflict

    • Executive Vision & Foresight

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Case Study 3: Influence & Alignment During a Major Merger

Merging two large internal organizations into one scalable operating system for a 250M+ subscriber streaming company

Role: Manager, Technology Services (led two multidisciplinary teams)
Scope: Brought in to lead one team; assumed leadership of a second broad-scoped team after an adjacent manager departed. Influenced senior leaders across Live Events and corporate user support, including C-level stakeholders.

  • The organization was broadly split into two verticals: Studio and Corporate. Each side had its own versions of support functions: tools, processes, escalation paths, and chains of command. As the company continued to scale rapidly, continuing to grow these verticals separately no longer made strategic, logistical, or fiscal sense.

    Leadership set out to merge the Corporate and Studio support organizations into one multifunctional operating system: new teams and roles, aligned service models, and a unified approach to supporting employees across the business. The work needed to happen at speed, with transparency, and without degrading a support structure that was already working, even if not optimally for a scaling company.

  • This was a high-stakes internal merger involving dozens of employees and multiple concurrent workstreams. The risks of stalling or executing poorly were significant:

    • Sunk cost and wasted effort after months of planning and global leadership involvement

    • Burnout across managers and employees during a non-linear, months-long transformation

    • Loss of trust and reduced goodwill for future transformations

    • Service degradation, an end state worse than the starting state

    Visible symptoms showed up early: slow decision-making, confusion over responsibilities, unclear ownership, and employee feedback about inefficient processes. Even in a healthy political environment, operational complexity can stall progress if the operating mechanisms aren’t explicit.

  • I helped lead the integration by combining systems thinking, executive communication, and change leadership.

    1) Evaluate the status quo and model the tradeoffs
    We assessed what was working, what wasn’t, and where a merger would improve outcomes or introduce breakpoints. Workstreams included tools, processes, communication paths, escalation models, user needs and profiles, and employee skills/gaps.

    2) Communicate the North Star and build commitment
    Once a plan was drafted, we communicated a clear “North Star” vision to generate excitement and commitment. The culture supported a memo-driven approach, so we used written narratives, executive briefings, Q&A sessions, and stakeholder updates to keep information flowing and to reduce uncertainty.

    3) Lead the change with ADKAR-informed practices
    Although not rigidly formalized, the work followed an ADKAR-like pattern: create Awareness, build Desire, provide Knowledge, ensure Ability through support and training, and Reinforce through iteration and recognition.

    4) Observe, iterate, and reinforce
    We created feedback loops to measure what was working, tune what wasn’t, and make adjustments quickly. Alignment wasn’t a single event, it was the result of continuous clarification, iteration, and reinforcement.

  • The turning point came when employee feedback shifted from generalized “friction” to themes of alignment, partnership, and collaboration. Service and execution indicators improved as the new operating model matured, including:

    • Customer support outcomes (e.g., time to resolution, throughput, quality)

    • Project velocity and delivery confidence

    • Morale and team efficacy during a prolonged transformation

    One durable artifact of the integration was a new company-wide operating system: the formation of the Technology Services group, built to scale support across both sides of the business

  • During the hardest portions of the transition, sustaining trust mattered as much as the plan. One direct report shared feedback that stayed with me:

    “You’re extremely gifted at helping further develop skills that we may have already thought were fully developed… You make everyone feel comfortable coming to talk to you about pretty much anything.”

    In a high-change environment, that psychological safety and coaching posture is what keeps teams resilient and adaptive.

  • This case directly shaped the competencies I teach in Leadership Bootcamp:

    • The Ambiguity Advantage

    • Executive Foresight & Vision

    • The Authentic Influencer

    • The Global Navigator

    • The Customer-Centric Workflow

    • The Resilient Professional

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