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Derek Cheng

@derekcheng

Staff Machine Learning Engineer at Stack Overflow who co-built Question Assistant, raising question success rates by about 12%.

United States
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At Stack Overflow, I co-built Question Assistant, which helps developers improve draft questions with targeted guidance. Its launch to all question askers followed A/B tests that showed about 12% higher question success rates.

I now lead the machine learning and generative AI architecture for the developer knowledge platform, including model evaluation, retrieval-augmented generation prototypes, and MLOps practices. I use measured online outcomes to inform what ships.

At Mercari US, I built item recommendations serving 1,000+ requests per second at under 50ms, and AI-assisted listing tools that cut average listing time 35%. Earlier, at Northrop Grumman, I developed target recognition and maritime anomaly detection for operational aerospace systems.

Experience

Work history, roles, and key accomplishments

Stack Overflow logoSO
Current

Staff Machine Learning Engineer

Apr 2026 - Present (7 months)

Leads technical direction for production machine learning and generative AI on Stack Overflow's developer knowledge platform, setting architecture standards, evaluation practices, and launch criteria. Owns the hybrid ML + generative AI architecture behind Question Assistant, including TF-IDF classifiers and Google Gemini feedback generation.

Stack Overflow logoSO

Senior Machine Learning Engineer

Aug 2023 - Apr 2026 (2 years 8 months)

Co-developed Question Assistant, an AI feature that reviews draft questions and helps developers add missing context, attempted solutions, error details, and minimal reproducible examples. Ran A/B tests measuring ~12% higher question success rates, leading to the feature's launch to all question askers.

Mercari US logoMU

Machine Learning Engineer

Mercari US

Jun 2022 - Apr 2023 (10 months)

Built computer vision and NLP models that auto-populate item metadata from listing photos and text, cutting average listing time 35% and raising production listing volume 20%. Designed and built an item recommendation service on Google Vertex AI using vector similarity search, sustaining 1,000+ requests per second at under 50ms latency.

Northrop Grumman logoNG

Machine Learning Software Engineer

Aug 2019 - May 2022 (2 years 9 months)

Developed GPU-accelerated Automatic Target Recognition for a defense air-vehicle platform using residual CNNs in TensorFlow and Python, detecting and classifying targets in Synthetic Aperture Radar imagery. Developed supervised and unsupervised maritime anomaly detection on large, imbalanced vessel-tracking data, extracting time-series features with TSFRESH.

Northrop Grumman logoNG

Modeling & Simulation Systems Engineer

Oct 2018 - Aug 2019 (10 months)

Built a modeling and simulation framework to evaluate Sense and Avoid for a defense Unmanned Aerial System, with C++ interfaces wrapping ACAS-Xu logic and connecting to simulated flight controller, ADS-B, TCAS, and radar sensors. Created visualization tools for UAS behavior and collision-avoidance encounters.

Northrop Grumman logoNG

Systems Engineering Intern

Jun 2018 - Oct 2018 (4 months)

Developed an exportable C# flight dynamics model based on six-degrees-of-freedom performance tables. Built MATLAB automation to plot flight-log data and identify landing-gear and braking faults, replacing manual review of individual logs.

Education

Degrees, certifications, and relevant coursework

Georgia Institute of Technology logoGT

Georgia Institute of Technology

Master of Science, Data Analytics

2020 - 2023

Pursued a Master of Science in Data Analytics with a focus on Computational Data Analytics.

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