Lindsey Whitley

Hi, I'm Lindsey.

Software Engineer specializing in observability, developer experience, security, cloud operations, and building product features

I love the feeling of accomplishment that only comes with a truly creative solution to a puzzling problem.

Follower of Jesus. Writer of Code.

Bonusly 2024 - Present

Primary CloudOps Engineer & Product Engineer

I wear multiple hats at Bonusly, spanning infrastructure, security, and product development. On the infrastructure side, I've led efforts to reduce complexity by migrating from Kubernetes to Heroku, doubling down on monolithic architecture, and strategically leveraging vendors instead of building custom solutions.

I've expanded into security engineering, partnering with penetration testing companies to identify and remediate vulnerabilities, conducting comprehensive access audits, and leading our SOC II compliance preparation efforts.

On the product side, I work extensively on Bonusly's rewards catalog—integrating new vendors, performing significant refactoring to improve maintainability, and developing billing system updates to support business growth.

Gusto 2017 - 2024

Developer Experience & Data Platform Engineering

From 2019 to 2024, I focused on Developer Experience, building tools that helped engineers move faster and providing deep observability into our deployed systems. I gained extensive experience implementing and monitoring Datadog metrics, logs, and traces across monoliths and microservices. Our team successfully reduced costs without sacrificing critical insights and improved time-to-detect issues without increasing spend. I implemented and achieved SLOs for CI infrastructure performance and reliability, and improved our data migration processes.

Earlier at Gusto (2017-2019), I helped build a Data Lake and Data Warehouse from scratch on the Data Platform Engineering team. I built ETLs that moved vital business information from Google Docs and REST endpoints into our data infrastructure, and simplified self-service analytics for the data team.

Background

In college, I got my first taste of coding with Matlab and Python. I found that of all my classes, I worked most voraciously on computer science and could not stop until I found solutions. Post-graduation, my favorite part of work was writing Excel macros to track the winery's maintenance data, which led me to enroll in App Academy to build a proper software engineering foundation in Ruby on Rails and React.

Throughout my career, I've used Terraform to manage AWS resources, conducted hundreds of technical and behavioral interviews, and participated in hiring decisions for interns, new grads, and experienced engineers. Driven by my desire to solve real problems with software, I continue to learn every day and love being part of teams building products that positively impact the world.

Technical Skills

Infrastructure & Cloud

  • AWS (IAM, S3, Lambda, EC2)
  • Terraform
  • Kubernetes
  • Heroku

Observability

  • Datadog (APM, Logs, Metrics)
  • Monitoring & Alerting
  • Distributed Tracing
  • SLOs & SLIs

Languages & Frameworks

  • Ruby on Rails
  • Python
  • SQL
  • React

Security & Compliance

  • Penetration Testing Remediation
  • Access Audits
  • SOC II Preparation
  • Security Best Practices

AI & Development

  • AI-Assisted Development
  • Prompt Engineering
  • LLM Integration
  • Code Generation & Review

Projects & Publications

Blog Publications

To take my own learning deeper, share experiences, and spread knowledge, I've written on various topics for the Gusto Engineering blog, in addition to editing and shepherding posts for teammates.

Read My Posts →

Basketball Team Maker

This project serves primarily to save me time when the next season rolls around for the recreational basketball league that I play in. Instead of manually creating balanced teams, I have the machine make them. As I hit new edge cases, I build new features.

Datadog Certification

Demonstrated knowledge of APM fundamentals, instrumentation, visualizations, and troubleshooting.

View Credential →

Let's Connect

I'm always interested in connecting with fellow engineers, discussing infrastructure challenges, or exploring new opportunities.