Skyler Insler
Verified Expert in Engineering
Engineering Lead and Developer
New York, NY, United States
Toptal member since February 5, 2026
Skyler is a senior engineering leader with over 18 years of experience building full-stack software, cloud-native web and data infrastructure, and implementing AI workflows at scale. He has defined technical strategies, led senior engineering teams, and partnered with non-technical teams to deliver lasting solutions used by millions of daily users. Skyler is a hands-on contributor across architecture, implementation, and organizational execution.
Portfolio
Experience
- Full-stack - 18 years
- SQL - 18 years
- Amazon Web Services (AWS) - 16 years
- Software Architecture - 16 years
- Python - 10 years
- Data Engineering - 9 years
- AI Pipeline - 7 years
- Agentic AI - 2 years
Preferred Environment
Python, SQL, JavaScript, Web, Full-stack, Back-end, Cloud Architecture, AI Architecture, AI Agents, Data Engineering
The most amazing...
...single-file commit I've pushed reduced CPU utilization from 99% to 1% on a web server receiving 100,000 requests per second.
Work Experience
AI & Data Engineer
Private Clients
- Built and deployed production AI pipelines and agents to power native AI applications.
- Focused on integrating LLMs and custom models with proprietary data workflows for scalable, low-latency applications.
- Owned system architecture, implementation, and end-to-end delivery from design to deployment.
Principal Software Architect, AI Initiatives
Ziff Davis
- Partnered with CTO to define and implement generative AI (genAI) strategies across the conglomerate's dozens of business units (BUs).
- Built web-based AI agents and tools leveraging LLMs and Chain of Thought techniques, accelerating the adoption of AI tools for internal productivity.
- Deployed content generation pipelines using proprietary data and retrieval-augmented generation (RAG) for real-world production use cases.
- Spearheaded regular company-wide forums discussing AI possibilities in daily workflows and for new product development.
Principal Software Architect
The Everyday Health Group
- Established the division's first software architecture team, formalizing design standards and long-term strategies.
- Designed and reviewed technical approaches for software architecture and infrastructure across all engineering teams.
- Standardized development practices across the organization alongside the head of engineering, improving code durability and developer efficiency, while reducing the time-to-market of deliverables for key organizational stakeholders.
Director of Data Engineering
The Everyday Health Group
- Directed a group of 12+ data engineers, data scientists, and analysts, and 3 managers following a major acquisition.
- Integrated large-scale data operations of two global-leading online media brands with a wealth of proprietary user data.
- Integrated pipelines into a central data warehouse, standardized Redshift and Airflow operations at scale, managing hundreds of directed acyclic graphs (DAGs).
- Partnered primarily with product development, marketing, analytics, and business development to deliver critical data solutions, supporting websites and apps with millions of MAUs, as well as advertising, sales, and business steering.
- Implemented data privacy and security practices for healthcare-related data, in compliance with expanding regulations such as GDPR/CCPA, as well as serving as a point person for sensitive legal and law enforcement DSAR requests.
Senior Software Architect
The Everyday Health Group
- Designed and built a proprietary lead generation delivery platform, responsible for millions in revenue quarterly.
- Collaborated with sales team members to build lead gen products, unlocking millions in new sales opportunities.
- Spearheaded mission-critical migration and merging of two business units’ email infrastructure to a new ESP, working closely with multiple Engineering teams, as well as marketing teams responsible for tens of millions of daily sends.
- Redesigned the data and services layers with serverless architecture and a NoSQL user database, which dramatically reduced operational costs (over 90%) while vastly improving latency, schema flexibility, and allowing for limitless scale.
- Orchestrated seamless migration of 20+ years of user profile data to new API and data layer with zero downtime.
Software Architect
Ziff Davis
- Designed and built from scratch the initial version of the company’s central data management platform, the foundation for which is still in use today, nearly 15 years later.
- Architected and built an infinitely scalable logging system with a customizable signal schema for user web activity across any website.
- Automated semantic content segmentation of web content, and user segmentation based on web browsing behavior of that content.
Senior Software Engineer, Team Lead
Vindico
- Led the team responsible for the architecture, development, and operations of all video ad serving, data collection, and analysis efforts for the business’s core product offering in the nascent online video advertisement industry.
- Contributed to the development of the industry-standard video ad serving specification (VAST), still in use today.
- Vastly improved cost efficiency, scalability, and ease of development for the entire tech operations and stack by migrating to the new cloud technology offered by AWS.
Experience
Production GenAI Pipelines
One pipeline for a leading broadband analysis firm generated location-specific content for inclusion on production web pages:
• First, new data would trigger an analysis using Google's Vertex, producing a structured JSON output.
• A geographic research agent would then generate location-specific context using sources like Wikipedia.
• Next, a multi-step workflow would integrate the outputs from preceding steps to generate draft content using OpenAI's API.
• A React-based website enabled human reviewers to configure LLM instructions, inspect detailed pipeline run history, and edit or re-run individual steps.
• Then, a review agent would evaluate the analysis and content outputs for accuracy, tone, and alignment with existing content stored in a custom vector database.
• Finally, an optimized output would then be selected for deployment to production, with a web interface for human intervention to choose from multiple outputs, edit, or postpone deployment.
Retool Applications for Hospitality Business
Full-service Event Booking and Management System
• Custom components for an interactive Calendar view (similar to Google Calendar)
• Self-service UI for booking the calendar, maintaining event and production details, and semi-automated communication with performers and staff
• Client-tailored workflows to facilitate management of events from booking and confirmation, marketing and advancement, "day of show" production management, and settlement
• Two-way integration with the client's employee scheduling software
• Database and secure, self-service web form for performer document and information collection
• Automated internal and external email communication with templating
Payroll Generation and Employee Access for Tipped Workers
• CRUD UI for employee shift reports
• Customized tip pool calculation and payroll preview
• Integration with payroll service provider
• Secure employee self-service portal with detailed shift tip reporting
Demos and more can be provided upon request.
Skills
Libraries/APIs
Node.js, REST APIs, React, OpenAPI, Stripe, HubSpot API, Claude API, OpenAI API, Terragrunt, Beautiful Soup
Tools
Apache Airflow, Retool, Terraform, RabbitMQ, Amazon Kinesis Data Firehose, BigQuery, Amazon CloudFront, Amazon Cognito, Cloud Development Kit for Terraform (CDKTF), Looker, Snowplow Analytics, Google Analytics, Amazon Elastic MapReduce (EMR), Apache Solr, Amazon Simple Queue Service (SQS), Amazon Simple Notification Service (SNS), Amazon Elastic Container Service (ECS)
Languages
Python, JavaScript, HTML, CSS, SQL, PHP, Snowflake, Java, TypeScript, C#, C#.NET
Paradigms
Database Design, REST, API Architecture, REST API Architecture, Web Architecture, MapReduce
Platforms
Amazon Web Services (AWS), AWS Lambda, MacOS, Amazon EC2, AWS IoT, Google Cloud Platform (GCP), Apache Kafka, Databricks, Vertex AI, Firebase, AppsFlyer, Windows, Linux, Web, SolrCloud, Apache RocketMQ, Docker
Storage
Amazon DynamoDB, Redshift, Databases, Relational Databases, Microsoft SQL Server, NoSQL, Data Pipelines, Redis, PostgreSQL, MySQL, Amazon S3 (AWS S3), Amazon Aurora, Data Lakes, Data Lake Design, Apache Hive
Frameworks
Flask, Swagger, Spark, Apache Spark, Django, Agentic Frameworks, Bootstrap, .NET, Hadoop
Industry Expertise
Project Management
Other
RAG Pipelines, Cloud Architecture, Full-stack, Software Architecture, Database Schema Design, Entity Relationships, Technical Design, Software Design, System Architecture, API Design, Data Warehousing, Data Warehouse Design, Amazon Redshift, Relational Database Services (RDS), Data Engineering, APIs, AI Architecture, Retrieval-augmented Generation (RAG), Generative Artificial Intelligence (GenAI), ETL Pipelines, Full-stack Development, Web App Deployment, Architecture, CI/CD Pipelines, Amazon RDS, Technical Leadership, RESTFul APIs, API Integration, Cloud Infrastructure, Large Language Models (LLMs), Large Language Model Operations (LLMOps), Multistage LLM Chains, RAG Architecture, Agentic AI, FastAPI, Amazon Kinesis, Code Review, Technical Reviews, Software Requirements Specifications (SRS), UML Diagrams, Google BigQuery, Amazon Managed Workflows for Apache Airflow (MWAA), AI Agents, AI Pipeline, ML Pipelines, OpenAI, Vertex, Artificial Intelligence (AI), payment processing api, HubSpot CRM, User Interface (UI), QuickBooks Online, Point of Sale, Consulting, Agentic RAG Systems, Open-source LLMs, Vector Databases, Serverless, Directed Acrylic Graphs (DAG), Data Privacy, Data Security, Data Modeling, Data Science, Data Analysis, Data Analytics, General Data Protection Regulation (GDPR), California Consumer Privacy Act (CCPA), Compliance, Recommendation Systems, Content Personalization, Email Marketing, Push Notifications, Localytics, Web Scraping, Terraform Cloud, Retool Database, Retool Workflows, Back-end, Internet of Things (IoT), LangChain, Amazon API Gateway, API Gateways, Load Balancers, IIS, MSMQ, VAST, Ad Serving, Video Ads, Tracking, Elastic Load Balancers, AWS Cloud Architecture, Data Management, Data Management Platforms, DMP, Google MapReduce, Semantic Segmentation
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