Jitan Gupta

Software Engineer

Mumbai, India10 yrs 4 mos experience

Most Likely To SwitchAI Enabled

Key Highlights

Expert in AI-native cloud infrastructure development.
Proven track record in multi-tenant SaaS migrations.
Strong advocate for responsible AI deployment.

Stackforce AI infers this person is a SaaS expert with a focus on AI-driven solutions and cloud infrastructure.

Contact

Skills

Core Skills

Azure Kubernetes Service (aks)Api DevelopmentAzure Ai Foundry.net CoreSoftware Development

Other Skills

HelmVector DatabasesMulti-Tenant ManagementJSON Web Token (JWT)GitTest-Driven DevelopmentSOLID Design PrinciplesMS SQLEntity Framework (EF) CoreContinuous Integration and Continuous Delivery (CI/CD)SentryJavaScriptC#Microsoft AzureArgoCD

About

AI is moving fast. Most engineering teams are adapting it without a security model, without guardrails, and without understanding the risks they're inheriting. I'm working to change that — through deep technical content that helps engineers and teams adapt AI responsibly. Not theory. Real production patterns, real tools, real limitations. By day, I'm a Senior Engineer at Leah, building AI-native cloud infrastructure on Azure and Kubernetes in the legal tech space. 10 years of production work — multi-tenant SaaS at scale, microservice migrations, zero-downtime deployments — is what shapes everything I teach about AI adaption. On YouTube and LinkedIn, I break down: — AI agent architectures and their security implications — Context engineering for AI-assisted development — Autonomous workflows: what works, what breaks, and what to check before deploying — Platform engineering in the age of AI I believe the engineers building with AI deserve real analysis, not hype. That's what I publish. All content and independent work is my own — created on my own time, with my own resources.

Experience

10 yrs 4 mos

Total Experience

2 yrs

Average Tenure

2 yrs 4 mos

Current Experience

Leah (formerly contractpodai)

Senior Engineer

Feb 2024 – Present · 2 yrs 4 mos · Mumbai, Maharashtra, India · Hybrid

Azure VM to AKS Migration (In Production)
Architecting and executing the migration of 14 microservices from Azure VMs to AKS for 400+ tenants
Implemented AGIC ingress controller with YARP for tenant-based version routing, supporting the last four releases simultaneously
Designed a region-by-region rollout strategy minimizing blast radius during migration
Built GitOps pipeline with Helm charts and ArgoCD for traceable, auditable deployments
Achieved auto-healing infrastructure with 99.9% uptime and automatic scale-down during off-peak hours
AI Deployment Orchestration – Internal Ops Tooling – POC
Designed RAG-based system to automate tenant upgrade decisions using Azure AI Foundry and Qdrant
Integrating Jira Stories/Bug data, feature usage metrics, and release notes for intelligent deployment recommendations
Expected to reduce deployment planning from 2 hours to 10 minutes per release cycle
User Management System
Led the migration of the User Management System from Microsoft Membership to Identity, transitioning from .NET Framework to .NET Core.
Currently migrating to a centralized Identity System using Identity Server, ensuring scalability, security, and Single Sign-On (SSO) capabilities.
Conducted a Proof of Concept (PoC) for migration, including a client-wise rollout & fallback mechanism for a seamless transition.
Writing complex business logic, performing code reviews, mentoring team members, and documenting best practices for long-term maintainability.
Impact: Eliminated technical debt, enhanced scalability and security, reduced maintenance costs, and made it easier to develop new features efficiently.

Azure Kubernetes Service (AKS)Azure AI FoundryHelmVector DatabasesAPI DevelopmentMulti-Tenant Management+13

Kaplan

2 roles

Lead Engineer

Jul 2023 – Feb 2024 · 7 mos · Hybrid

Led backend development and managed a team of 3 engineers to migrate a legacy application, ensuring a smooth transition without disrupting existing users.
Conducted PoCs and integrated third-party solutions, picking the right tools to balance performance, cost, and long-term maintainability.
Focused on writing efficient and maintainable code, running regular reviews to keep performance high and technical debt low.
Impact: Improved application performance and expanded its reach to mobile and tablet users, making it more accessible across devices.

API DevelopmentMicrosoft SQL ServerGitHubAzure Blob Storage.NET APIsgRPC+13

Senior Engineer II

Dec 2021 – Jun 2023 · 1 yr 6 mos · Hybrid

Debugged and optimized complex microservices applications, quickly identifying root causes and improving system stability.
Built and shipped new features that directly improved the application’s usability and adoption.
Led stage migrations and production releases, ensuring smooth rollouts with minimal disruptions.
Impact: With new features and optimizations, more teams and users started actively using the platform.

API DevelopmentMicrosoft SQL ServerGitHubASP.NET MVCgRPCAzure Kubernetes Service (AKS)+9

Nec software solutions (india)

2 roles

Senior Software Engineer

Promoted

Jul 2021 – Dec 2021 · 5 mos · On-site

Led the upgrade from Bootstrap 3.3.7 to 4.1, improving the application's UI/UX and making it more modern and responsive.
Focused on optimizing frontend performance, ensuring a smoother experience across devices while reducing tech debt.
Impact: The upgrade enhanced accessibility, improved performance, and provided a better user experience across web and mobile.

API DevelopmentASP.NET MVCSoftware DevelopmentSQL.NET FrameworkBootstrap (Framework)+2

Software Engineer

Feb 2019 – Jun 2021 · 2 yrs 4 mos · On-site

Worked in agile sprints to integrate new features while maintaining high-quality code through TDD and a strict Code Review Policy.
Conducted Proof of Concepts (PoCs) to test and validate ideas, presenting insights to the Product Manager before rolling out implementations.
Impact: New features increased platform adoption, leading to more teams and users actively engaging with the product.

API DevelopmentMicrosoft SQL ServerSoftware DevelopmentDebuggingAngularEntity Framework+2

Neosoft technologies (a cmmi level 5 organization)

Software Engineer

Sep 2016 – Feb 2019 · 2 yrs 5 mos · Mumbai Area, India

Client-side: Mahindra Finance
Roles & Responsibilities:
Developed new Fixed Deposit App modules, including Quick Buy and Quick Buy Support, improving user experience and transaction efficiency.
Designed a Visual Studio template to streamline the creation of internal applications, reducing setup time for new projects.
Provided hands-on training to freshers, guiding them through best practices and accelerating their onboarding process.
Led the migration of an existing project to .NET Core, collaborating with freshers to ensure a smooth transition while upskilling the team.

API DevelopmentMicrosoft SQL ServerASP.NETADO.NETSoftware DevelopmentjQuery+2

Artcarro art services pvt. ltd.

Web Developer

Dec 2015 – Sep 2016 · 9 mos · Mumbai Area, India

Led a team of 3 developers to build and enhance the e-commerce platform for handmade artwork, overseeing development, code reviews, and deployments.
Designed and developed the platform from the ground up, ensuring a scalable and user-friendly experience.
Iterated on features based on user feedback, continuously improving the platform’s functionality and performance.
Integrated a payment gateway, enabling secure and seamless transactions for buyers and artists.
Managed end-to-end development, including deployments, enhancements, and overall platform maintenance.

Microsoft SQL ServerPayment GatewaysASP.NET MVCADO.NETSoftware DevelopmentjQuery+3