I design and execute enterprise AI strategy, digital transformation, and the operating architecture that makes it permanent — from agentic automation to IPO-ready data infrastructure.
About Sunita
A CDO and transformation leader who turns ambitious technology strategy into durable competitive advantage.
Over 15+ years, I've held executive roles at some of the most demanding environments in tech — leading $900M+ revenue automation at Yelp, co-leading the Udemy NYSE IPO, executing full-stack AI transformation at a Khosla-backed robotics company, and enabling global expansion at Gap Inc. I don't just advise on transformation. I own it, drive it, and deliver it.
My edge is bridging the gap between visionary AI strategy and the operational rigor required to make change stick at enterprise scale. I speak the language of engineers and boards equally — and I know which levers actually move organizations.
See the full track record →AI Transformation Framework
AI readiness audit, data quality assessment, process mapping, and identification of highest-leverage automation opportunities across finance, ops, and GTM.
AI platform evaluation, LLM and agentic workflow design, data architecture for AI readiness, vendor negotiation, and build-vs-buy decisions with clear ROI models.
Phased production deployment with change management, AI governance frameworks, compliance controls, and security hardening — so AI ships safely and sticks organizationally.
KPI frameworks, real-time dashboards, continuous improvement loops, and the operating model that turns a project into a permanent competitive advantage.
AI in practice
Revenue Intelligence
At Yelp, led the transition from manual FP&A to ML-driven connected planning — integrating revenue signals, marketing activity, and operational data into a single predictive layer that Finance, RevOps, and GTM all ran on. Eliminated planning lag and improved forecast accuracy across a multi-product business.
Intelligent Automation
At Mighty Buildings (Khosla Ventures), designed the company-wide AI automation strategy — replacing manual workflows in production operations, procurement, and ITSM with intelligent systems. Built the vendor evaluation framework, automation architecture, and change management program to ensure adoption.
Applied GenAI
Currently building the AI analytics platform at Crewasis.ai — designing data capture systems, KPI frameworks, and GenAI-powered reporting pipelines for both internal operations and enterprise customers. MIT-certified in Applied GenAI for Digital Transformation.
AI Security & Compliance
Led enterprise security uplift at Mighty Buildings — implementing AI-enhanced threat detection, MFA, and a zero-trust architecture that reduced unauthorized access by 90% and incidents by 75% YoY. Simultaneously designed AI governance and compliance frameworks for board-level confidence.
Case studies
Yelp · 2017–2020
Transformed Yelp's fragmented commerce infrastructure into a unified AI-augmented billing and subscription platform — spanning Yelp.com, Reservations, Waitlist, and WiFi product lines. Led 45+ engineers and analysts through a full platform rebuild.
Udemy · 2020–2022
One of three executives who led the Udemy IPO. Owned enterprise data governance, AI/data modernization, compliance reporting, and investor-grade system architecture for 1,500+ employees globally — partnering directly with CFO, COO, and audit leadership.
Mighty Buildings · 2022–2024
Designed and executed AI-driven transformation across a 3D printing/robotics startup — automating operations, deploying intelligent cybersecurity, modernizing ITSM, and rationalizing the vendor ecosystem — while maintaining delivery velocity throughout.
Capabilities
AI Strategy
Data & Analytics
Enterprise Systems
Revenue Operations
Transactions
Security & Risk
Leadership Philosophy
After 20+ years leading transformations at Yelp, Udemy, Gap, and Mighty Buildings, I've learned that the most durable change demands equal investment in people, process, and technology. My leadership style is direct, decisive, and relentlessly outcome-focused — with the cross-functional fluency to align engineers, operators, and boards behind a single direction.
"The measure of a transformation isn't what ships on day one. It's whether the organization can sustain it long after you've moved on."
— Sunita RajaWork with Sunita
Whether you need a CDO for a transformation sprint, an interim COO while you scale, or a trusted advisor on AI strategy — I meet you where you are and deliver outcomes that last.
sunitaraja@gmail.com →Full-time Executive Role
COO, CDO, or VP Digital Transformation at the right company
Fractional CDO / AI Transformation
Strategy, roadmap, and program leadership · 1–3 days/week
Interim COO or Head of Operations
Full executive ownership during transitions or rapid scale
IPO & M&A Readiness Advisory
AI-ready systems, governance, controls, and audit prep