Career chronology
CV
I lead where people, customer experience, operations, engineering, and AI intersect.
Bobby Pierce · Contact me: https://www.linkedin.com/in/robertjpierce
Confidential
Independent AI/ML Contractor - Confidential
I contribute to AI/ML model development through dataset preparation, labeling, and evaluation of text and vision outputs. The contractor relationship began in August 2024 and continues alongside my other roles, with assignments undertaken at different times.
- Prepare and label data, evaluate text outputs, and provide human feedback for model training and evaluation workflows.
- Review responses for factual accuracy, grammar, hallucinations, and safety, including RLHF-style feedback.
- Evaluate vision model outputs for quality and safety within the requirements of each assignment.
Kalana Consulting
Independent Consultant
Independent consulting across AI enablement, product development, organizational advice, and Voice of the Customer. I advise leaders and build custom applications, internal tools, and websites through Kalana Consulting. This work runs alongside my role at Nerdy.
- Advise leaders on where AI can help, the changes it asks of an organization, and the role of human judgment in the work.
- Build custom applications, internal tools, and websites around the people who will use them.
- Help teams work through product decisions with customer, operational, and engineering perspectives in the same conversation.
- Use Voice of the Customer and frontline insight to identify improvements upstream of the next support contact.
Nerdy
AI Product Engineer
I moved into a dedicated engineering role after leading operations and cross-functional programs. My work brought customer-support knowledge, operational data, and AI tools into the applications teams used.
- Built the full-stack foundation for a knowledge base and a retrieval-augmented copilot.
- Implemented an agentic documentation pipeline that scanned engineering repositories, identified code changes, and drafted updated knowledge-base articles for human review before publication.
- Developed a CRM application that brought retention risks, account balances, and recovery work into the same view.
- Independently built a root-cause analysis pipeline with agentic and deterministic paths. I treated its deterministic findings as directional evidence for investigation.
Principal Program Manager, Operations Integration
I led programs across AI, CRM, workforce planning, and business platforms, working with operations, engineering, and data teams. The role combined program ownership with hands-on product and data-model development.
- Architected and built a replacement CRM, its customer data model, and migration work during a customer-service platform transition.
- Documented field lineage and the data dictionary, and partnered with engineers on contact-center integration.
- Brought leaders, analysts, and builders together to coordinate programs, quarterly commitments, and impact forecasts.
Director, Consumer Support Operations
I led customer support through several layers of leadership, with weekly performance and incident reviews. I worked on how managers coached, how teams used AI assistance, and how operating issues reached the people who could address them.
- Led the selection and deployment of an AI support assistant.
- Redesigned AI coaching prompts around customer sentiment, conversation stage, and the team's quality rubric.
- Directed the coaching rollout to retention teams and established regular operating reviews.
Senior Manager, Marketplace Operations
I brought together tutor engagement and operations support across course operations, quality, moderation, payments, and customer support. Workforce planning and leader development were central to the role.
- Led the first workforce-management platform implementation, participated in vendor evaluation, and owned the contract relationship.
- Partnered with Finance on headcount forecasts and resource allocation.
- Introduced Agile and Kaizen practices, with mentoring opportunities for leaders.
Chewy
Program Manager
I managed an employee-engagement program for peak-season readiness, coordinating concurrent projects and the teams delivering them. The program focused on enrichment, team cohesion, and gamification during the busiest part of the year.
- Organized the projects with a Lean/Agile Hybrid approach, daily standups, blocker tracking, and coordination across leadership levels.
- Worked with leaders on activities intended to support team readiness and employee experience.
- Used AI-assisted recaps to help track meetings and keep participants informed about the work.
Operations Manager II
I led managers and coaches in Chat operations. Alongside team leadership, I worked on the measurement and coaching tools we used to understand customer interactions.
- Redesigned the Chat productivity dashboard and worked with data partners on its model, calculations, and user acceptance testing.
- Developed interaction measures that separated agent response timing from the customer’s experience of waiting.
- Partnered with AI/ML and quality teams on scoring rubrics, utterance detection, and calibration.
- Managed AmplifAI onboarding for the chat team and trained participants in using the platform for coaching.
- Built coaching scorecards and a custom GPT, and taught eleven chat managers supporting roughly 180 to 200 agents how to use AI in their coaching work.
- Used SQL, Vertica, Excel, and Tableau to investigate operating questions and checked analysis with fellow managers.
- Helped Operations HR work through employee review calibration with AI-assisted comparison and human judgment.
Operations Manager I
I led managers and frontline teams in Voice and Email operations, with a focus on customer experience, coaching, and helping new hires move into their teams.
- Coached managers and partnered with Learning and Development on new-hire transitions.
- Automated recurring team communications and time-management tasks using Slack and Power Automate.
Apple
Store Manager
I led retail teams across customer service, sales, business accounts, store operations, and employee development. During my Store Manager tenure, I took responsibility for each of the departments below, working with fellow managers and team leaders to plan the work, develop people, and respond when the store's needs changed. My work at Wellington Green and Boca Raton included department handovers, service changes, and bringing teams together through store transitions.
- Area of Responsibility: Genius Bar Operations. Led service and support teams across staffing, appointment access, repairs, and the daily customer journey. I introduced a walk-in service approach, worked with the Lead Genius and experienced team members on training, and used team roundtables to surface problems with service processes and leadership consistency. When staffing changed, I adjusted coverage and cross-trained people across roles to support the service team.
- Area of Responsibility: Sales Leadership. Co-led Product Zone planning, floor leadership, and coaching with my fellow managers. At Boca Raton, I challenged an overextended quarterly plan and helped reduce it to three clear priorities, with weekly AOR reporting and regular accountability conversations. I also turned the team's ideas for the back-to-school season into a practical plan and meeting agenda, and worked with peers on the customer journey around online setup and Today at Apple sessions.
- Area of Responsibility: Business Team Leadership. Led business customer engagement and worked with Business Experts on account priorities, opportunities, and follow-through. I analyzed the customer database by industry, identified gaps in its categorization, and supported research and briefings with the Business Team. At Boca Raton, I helped the team put its own shared pipeline workflow into practice, alongside changes to CRM task management. I also delivered market-wide training on lead qualification, funnel management, conversion, and customer relationships.
- Area of Responsibility: Visual Merchandising. Led the visual team through a back-of-house remodel and oversaw store presentation and merchandising work. I selected a Visuals Mentor and worked with the team and other managers to address installation constraints as a store upgrade progressed. I also changed the Visuals Lead assignment into a formal career experience, giving the role a clearer place in employee development.
- Area of Responsibility: Inventory Operations. Led inventory operations and partnered with Operations Experts as they led physical inventory. I kept regular communication with the team's leaders, supported operations during peak periods, and worked alongside the team when they needed help. I also coached an Operations Expert through a leadership career experience, building on our regular feedback and collaboration.
- Area of Responsibility: People Leadership. Led coaching, hiring, employee development, and store training. I held team feedback sessions and used surveys to shape training topics and timing, formed a Mentor Team, and built a training calendar with staff and subject-matter experts. I also ran hiring events, supported interview preparation, coached colleagues through department transitions, and introduced weekly follow-up on development conversations.
- Area of Responsibility: Scheduling and Workforce Management. Owned scheduling across sales and service teams, balancing customer demand, available skills, employee needs, and payroll. I redesigned the scheduling workflow so each part of the process had a clear owner, used Kronos reporting to plan coverage and review payroll, and coached another manager through those decisions during an AOR handover. I also built an attendance tracker and checked it against weekly reporting so managers had a consistent basis for follow-up.
Senior Operations Manager, Order Support (assignment)
My Order Support assignment extended my retail background into distributed-team leadership across business and consumer support. I helped managers build a shared team culture, respond to changing queue demand, and work together on coverage and operating decisions. The assignment overlapped my Store Manager tenure and is shown separately here.
- Onboarded remote team members into Sales Chat and Order Support and developed the managers supporting those teams.
- Built a shared culture for a virtual team while coordinating staffing across lines of business. When queues grew, I shifted people to support demand and worked with other leaders on coverage.
- Led weekly KPI meetings across Order Support teams, giving managers a regular forum to review the work and discuss operating needs.
- Asked managers to bring proposed coverage approaches forward, then worked with them to combine their ideas into a shared framework. The managers helped shape the way their teams would work.
- Coordinated with telecom carriers on delivery and activation escalations to address technical blockers across business and consumer support.
- Worked with U.S. and foreign government officials to apply U.S. export and embargo controls within SAP and other internal platforms.
Specialist, Genius, and Lead Genius
I began on the sales floor as a Specialist, moved into hands-on technical service as a Genius, and then took responsibility for Genius Bar leadership as a Lead Genius. Those roles connected product knowledge, repair work, customer communication, and the coordination of technical teams.
- Specialist: Helped customers find Apple products and solutions that fit what they wanted to do. I kept product knowledge current, answered questions throughout the customer journey, and helped maintain an organized sales floor so people could explore products and get support.
- Genius: Diagnosed hardware and software problems, carried out repairs, and managed the repair workflow from consultation through service follow-up. I helped maintain store systems, service parts, tools, and supplies, while working with colleagues on the queue and coaching customers through technical issues.
- Lead Genius: Led Genius Bar operations across multiple stores over the course of the role, supporting technical teams and helping store leaders work through operational problems.
- Lead Genius: Traveled to support operational improvements and led pilots for iterations of the Genius Bar operating strategy.
- Lead Genius: Presented findings and implementation recommendations to retail executives.
Pink Elephant Planning
Co-owner
I co-owned and ran Pink Elephant Planning, a custom stationery business. I designed the products, programmed the production equipment, and built the CRM and online store.
- Designed products and programmed laser-guided die cutters and four-color process printers.
- Built the CRM, store, customer-service, shipping, marketing, and social presence.
- Handled the business license, books, and accounting.