VP Engineering / CTO — C Squared Labs | Inference Search Partners
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C Squared Labs
VP Engineering / CTO · Hiring Now
VP Engineering / CTO · SF Bay Area · Full-Time

Build the architecture for AI's hardest knowledge problem.

C Squared Labs is turning massive unstructured data into precise enterprise intelligence. The company is beyond PMF, scaling with live design partners, and backed by one of the valley's largest Seed rounds. They need a VP Engineering / CTO who is still a force-multiplier on the keyboard, not just in the boardroom.

Seed
One of the valley's largest rounds
10
High-performing engineers to lead
30–50%
Of your time writing code
2
Interview steps. That's it.
The Role

Ultimate technical authority. Not an isolated exec seat.

You are the CTO and you still code. At least 30–50% of your time is IC-ing: solving the hardest architectural problems, defining what production-grade agentic AI looks like, and force-multiplying a team of 10 engineers already running fast.

You read a breakthrough paper in the morning. By the afternoon, the roadmap is updated and the team knows what to build. That's the pace here.

Why This Moment

Rare conditions. Real momentum.

🎯
Founding-level equity
One of the valley's largest Seed rounds. Early enough to shape everything, funded enough to build without constraints.
🧠
Technical frontier, for real
Multi-agent orchestration, hybrid retrieval, neuro-symbolic pipelines. No legacy codebase, no architecture debt to inherit.
✅
Beyond PMF with live design partners
You're scaling something proven, not validating a hypothesis. Design partners are live and the problem is massive.
What You'll Own

Six big things. All yours.

01 — Architecture
Design the Technical Vision
System paradigms, core architecture, and technical strategy to turn massive unstructured corpora into resilient, deterministic software.
02 — Culture
Institutionalize AI-Native Engineering
Mandate and master Cursor, Claude/Copilot agentic workflows, and custom prompt compilation loops across your 10-person team. Drastically increase throughput.
03 — Reliability
Force Reliability from Chaos
Design the guardrails, architectural standards, and evaluation frameworks that turn non-deterministic AI into enterprise-grade, production-hardened software.
04 — People
Set the Pace
Be the gravitational pull for a high-performing team. Mentor senior engineers, bridge business strategy to production reality, and hire people who raise the bar.
05 — Communication
Executive Strategic Communication
Structure complex technical trade-offs logically and communicate them clearly to leadership, the board, and external stakeholders. Board-ready when it counts.
06 — IC Work
Write Code
30–50% of your time is on the keyboard, solving the problems no one else can crack. You are a force-multiplier because you ship, not just review.
The Stack

What you'll be building with.

AI Coding
AI-Enabled Dev Mastery
Expert adoption of Cursor, Claude/Copilot agentic workflows, and custom prompt engineering compilation loops, mandated and modeled across the full team.
Agentic Infra
Multi-Agent Orchestration
Production-level experience with multi-agent systems, hybrid retrieval/search pipelines, and LLM-as-a-judge evaluator frameworks at enterprise scale.
Production Systems
Enterprise-Grade Reliability
Complex, production-hardened systems at scale. You know when a heuristic beats a neural model, and you build the eval frameworks to prove it.
Who You Are

Five things that make you the person for this.

IC
Still a Star Engineer
You write code with breathtaking speed. You're in Cursor every day. You solve the hardest systems problems directly, not just in Notion or in meetings.
Architecture
Battle-Tested Architect
You anticipate cascading failures before they happen. You've shipped complex production systems at scale and know exactly when a simple heuristic beats a neural model.
AI-Native
AI-Native (for Real)
You've mastered AI-enabled coding practices in a previous role. It's in your daily workflow, not your resume keywords. You bring serious momentum from modern AI architectures.
Leadership
Proven People Leader
You've directly managed, hired, and up-leveled engineering teams of 10+. You've built high-velocity engineering cultures, not just inherited them.
Communication
Lateral Thinker & Executive Communicator
When technical or organizational challenges hit a wall, you don't stall. You use structured reasoning to outline clear options and present trade-offs effortlessly to Dinkar, the board, and design partners. You're equally comfortable in a whiteboard session and a board deck.
The Founders

Built by people who've shipped AI at billions of scale.

DJ
Dinkar Jain
Co-Founder & CEO

Most recently VP of AI & Marketplace at Uber, leading AI strategy across the company's core platform. Before that, Head of Ads AI at Meta, overseeing 200+ ML engineers building personalization systems for 2B+ users. Also spent time at Alphabet, Amazon, and Boston Consulting Group.

MBA with distinction from Harvard Business School. BSE in Computer Science from the University of Michigan.

Uber Meta Alphabet Amazon Harvard MBA UMich CS
TS
Tilak Sharma
Co-Founder & Chief Engineer

Deep ML research and engineering background with a focus on generative AI systems. Tilak is the technical anchor at C Squared, designing the agentic infrastructure, data pipelines, and retrieval systems that power the platform.

Reads a paper in the morning. Ships an implementation by afternoon. The engineering bar you'll be building alongside.

ML Research Generative AI Agentic Systems Top-tier Tech
The Offer

What you get.

💵
Compensation
Very Competitive Cash
Market-leading base for a technical executive at a well-funded seed-stage company
🎯
Equity
Founding-Level Equity
One of the valley's largest Seed rounds. You're here early enough for it to matter.
⚡
Interview Process
Two Conversations
CEO + Chief Engineer. Short by design. They know what they want.
Recruiting facilitated by Inference Search Partners Shwetha Alampalli · Executive Search & Talent Advisor
Connecting exceptional talent with companies building the future of AI.
Grab time with Shwetha →
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