Yaswanth Chakka

CTO

Toronto, Ontario, Canada10 yrs 2 mos experience

Most Likely To SwitchHighly Stable

Key Highlights

Expert in building scalable engineering standards.
Proven track record in developing innovative AI-driven solutions.
Strong leadership in managing high-performing engineering teams.

Stackforce AI infers this person is a SaaS-focused engineering leader with expertise in AI-driven product development.

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Skills

Core Skills

Engineering ManagementSoftware ArchitectureApi Development

Other Skills

PythonCeleryFlaskElasticsearchRedisDockerLarge Language Models (LLM)RabbitMQAWSGo (Programming Language)Vue.jsMachine LearningAmazon Web Services (AWS)Amazon S3Amazon Lambda

About

I am a dreamer and a doer with a passion for building and leading high-performing teams. With a unique blend of technical prowess and strategic thinking, I excel at conceptualizing ideas, dissecting code, and implementing the latest standards to create innovative solutions. As a problem-solver, I thrive on using my creativity and technical know-how to develop elegant and effective solutions that generate revenue or save resources. With a track record of success, I bring a knack for innovation to every project. Over the past ~10 years, I have honed my skills in a diverse range of technologies, including cloud computing, web application development, machine learning, and software architecture. I am constantly engaged in experimental development and rapid prototyping, exploring new possibilities and pushing the boundaries of what can be achieved. https://github.com/Cyash

Experience

10 yrs 2 mos

Total Experience

2 yrs 6 mos

Average Tenure

6 yrs 2 mos

Current Experience

Bespoke metrics inc.

4 roles

VP of Engineering

Promoted

Feb 2026 – Present · 3 mos

Building agentic AI systems for construction risk management.

Staff Engineer

Promoted

Jan 2022 – Feb 2026 · 4 yrs 1 mo

As a Staff Engineer and mentor, I successfully managed a backend team of 7 while wearing multiple hats to establish and oversee 50+ core microservices. I played a pivotal role in backend development using Python, Flask, Redis, SQLAlchemy, Elasticsearch, Celery + Beat, RabbitMQ, and Docker, ensuring seamless functionality and performance.
One of my notable achievements was designing and developing an OAuth 2.0 Protocol from the ground up, enabling secure client integrations via APIs. I also architected Single Sign-On (SSO) and User Provisioning (SCIM v2.0) solutions for enterprise clients, streamlining authentication and user management.
To enhance efficiency, I built a high-performance task processing system capable of handling ~1,000 I/O-bound tasks per minute. I also collaborated with third-party vendors to ingest customer data, enabling precise calculations for aggregate and pending backlog contracts.
Additionally, I developed a CLI-based code generation tool leveraging Tree-sitter, Retrieval-Augmented Generation (RAG), and LLMs, automating approximately 15% of development work and significantly boosting engineering productivity(later replaced with Cursor. nevertheless a great learning!).
Beyond technical contributions, I played a key role in hiring and onboarding engineers, setting high standards for hiring, development, and architectural best practices. My work has not only driven the success of the organization but also established scalable engineering standards that others continue to follow.

Engineering ManagementPythonCeleryFlaskElasticsearchRedis+3

Senior Engineer

Promoted

Jul 2021 – Jan 2022 · 6 mos

PythonFlaskAPI DevelopmentElasticsearchRedisRabbitMQ+3

Software Engineer

Mar 2020 – Jul 2021 · 1 yr 4 mos

Partnerstack

Software Engineer

Sep 2019 – Feb 2020 · 5 mos · Toronto, Canada Area

Engineering.com

2 roles

Platform Developer

Promoted

Sep 2018 – Sep 2019 · 1 yr

As a Platform Developer, I was responsible for providing cloud platform architecture and leading development efforts with a cloud-first approach. I continuously improved the resilience of our infrastructure on AWS, handling approximately 2k requests per second, ensuring high availability and performance of our applications.
One of my significant accomplishments was developing a serverless machine learning application using Python and AWS to generate personalized content for email newsletters and campaigns. This platform gave us full control over data and resolved challenges related to campaign analytics, resulting in estimated cost savings of $10-15k per year.
Additionally, I developed another serverless application using Python and AWS to generate Accelerated Mobile Pages (AMP) and audio books from existing articles. This application generated revenue of over $70K per year and increased site traffic by approximately 20%.
Furthermore, I played a key role in building projects.engineering.com from scratch, utilizing Go-Lang, ECHO, Elastic Search, GORM, Docker, and contributing to the front-end using Vue.Js and ES6. I also built a recommendation engine from scratch using machine learning techniques, implemented on a serverless architecture.