Head of AI & Engineering · Two-time founder · Advisor

I build AI systems that reach millions.

Agent platforms at Eightfold AI. Semantic search at Walmart.com. Conversational AI at Amazon Alexa. Machine translation at eBay that added $1B+ in GMV. I advise CEOs, CTOs, founders, and investors on what to build, how to build it, and what it is worth.

Accepting a limited number of engagements Agentic AI, search & language — for enterprise leaders, founders & investors
Portrait of Pankaj Rajan
Pankaj Rajan Head of AI & Engineering, Eightfold AI San Francisco Bay Area
Leadership experience at
  • Eightfold AI
  • MarkovML
  • Amazon Alexa AI
  • Walmart Global Tech
  • Ayasdi AI
  • eBay
  • Microsoft
  • AMD
15+
Years leading AI in production
Millions
Systems that handle millions of users
$8M
Venture funding raised as co-founder & CPTO of MarkovML
$1B+
Incremental GMV from ML systems I helped build
Who I help

Advice built on having done the work

Choose your seat at the table. Each engagement draws on the same track record: shipped products, built teams, and raised capital.

Decide where AI moves revenue and margin — and who should build it.

How I help

  • AI strategy and investment roadmap the board can track
  • Build, buy, or partner decisions on models and vendors
  • Board briefings on AI opportunity, cost, and risk
  • Hiring and assessing senior AI leadership

Track record

  • Extended leadership team at Eightfold AI, owning headcount, budget, and vendor spend
  • Presented strategy and risk to the MarkovML board as co-founder
  • Doubled Alexa user satisfaction while cutting cost to serve ~15%
Start with a conversation
The challenge

Where AI programs stall

The obstacle is rarely the model. It is strategy, platform, governance, and organization — and those are leadership problems.

Investment without return

Pilots multiply, but few reach production — and fewer show up in the P&L.

Risk managed after launch

Quality, safety, and compliance are assessed once customers are already exposed, not before release.

Fragmented platforms

Each team builds its own AI stack, multiplying cost and slowing every subsequent launch.

An organization built for a pre-AI era

Delivery slips while competitors use AI to ship faster with the same headcount.

Services

How I help

Engagements are fixed-fee and scoped to outcomes. Begin with a strategy engagement, or bring me in to lead execution.

01 2 weeks · the starting engagement

AI Value Diagnostic

The place most clients start. In two weeks I interview your leadership, review your architecture, data, and pipeline of AI work, and identify where AI will move revenue, margin, or cost to serve — and where it will not.

Three ranked bets with owners, budget, KPIs, and a 90-day plan
02 6–10 weeks · hands-on

Agent & Search Platform Build

I lead your team to one shared platform for agents and search — orchestration, memory, tool access, retrieval, guardrails, tenant isolation, and evaluation gates — and ship the first use case on it.

A production pilot measured against a baseline, on a platform your teams reuse
03 1–2 weeks · before the term sheet

AI Technical Due Diligence

For venture funds and acquirers: an operator’s assessment of an AI company — architecture, data advantage, evaluation rigor, inference economics, and team — before you commit capital.

An investment memo with strengths, risks, red flags, and the questions to ask
04 Ongoing · advisory or board seat

Advisory & Board Roles

For AI companies and their investors: ongoing counsel on technical strategy, senior AI hiring, and enterprise readiness — as an advisor or board member.

A senior operator in your corner between board meetings
What I have built

From first code to production

AI systems I have architected and led to production — agents, workforce intelligence, search, translation, and conversational AI — used by millions of people.

Agents · Platform

Enterprise agent platform

A shared runtime and authoring layer for agents — orchestration, memory, tool access, guardrails, tenant isolation, and a built-in evaluation layer — so several product lines ship agents on one foundation instead of one stack per team.

Workforce intelligence

Conversational workforce analytics

An agentic analyst for HR and business leaders: plain-language questions about skills, readiness, and talent become answers with the analysis behind them — no analyst queue.

Agents · Human-in-the-loop

Long-horizon hiring agent

An agent that carries a candidate from first search to offer letter over weeks of text conversation, with human checkpoints at every consequential decision.

RAG · Memory · Knowledge graph

Personalized career guidance

A coaching assistant grounded in a skills knowledge graph, with long-term memory that carries each person’s goals and context across sessions.

Platform · Compliance

Private enterprise AI platform

Model routing, retrieval, fine-tuning, inference, and agent workflows on multi-tenant infrastructure for defense and education customers, certified to SOC 2 Type II.

Quality · Safety

Evaluation & release gating

Offline and online evaluation that gates every model and agent change before it reaches users — applied to voice assistants, search, and enterprise agents.

Search · NLP

Semantic search at e-commerce scale

Query understanding — entity extraction, intent classification, and query rewriting — for one of the largest product catalogs in the world, with +85% long-tail understanding.

Conversational AI

Open-domain conversational AI

Generation, retrieval, relevance, and safety models for a consumer voice assistant, doubling user satisfaction while cutting cost to serve ~15%.

NLP · Translation

Machine translation for global commerce

A production translation engine that opened cross-border marketplaces to buyers in their own language, adding $1B+ in GMV.

Expertise

Language, search, and agentic systems — built and operated at enterprise scale.

Applied Domains

  • Workforce intelligence & talent
  • Conversational analytics
  • Hiring & career agents
  • E-commerce search & discovery
  • Voice & conversational assistants
  • Defense & EdTech AI

Agent Systems

  • Agent runtimes & harnesses
  • Orchestration & authoring tools
  • State, context & long-term memory
  • MCP & tool interfaces
  • Multi-agent coordination
  • Long-horizon workflows
  • Human-in-the-loop checkpoints
  • Guardrails, permissions & tenant isolation

NLP & Conversational AI

  • Entity recognition & linking
  • Intent classification
  • Machine translation
  • Open-domain dialogue & response generation
  • Response relevance models
  • Knowledge graphs
  • Multimodal assistants (voice + text)

Search & Ranking

  • Query understanding & rewriting
  • Semantic & hybrid retrieval
  • Learning-to-rank
  • RAG over proprietary data
  • Long-tail query handling
  • Offline retrieval & ranking evaluation
  • Search platform migrations at scale

Classification & Evaluation

  • Text & intent classifiers
  • Safety & policy classifiers
  • Agent & retrieval evals
  • Quality scoring & human review
  • Release gating & regression tracking
  • Production observability

Models & Platform

  • Model routing: frontier, open-source, private
  • PEFT / LoRA fine-tuning
  • vLLM inference
  • Python · PyTorch · Kubernetes
  • AWS · GCP · Azure
  • SOC 2 Type II · FedRAMP-aligned
Approach

A disciplined path to value

Every engagement follows the same sequence, so investment decisions rest on evidence rather than enthusiasm.

Diagnose · Weeks 1–2

Leadership interviews and a review of architecture, data, and delivery. We agree on the business number AI must move and measure today’s baseline.

Design · Week 3

Architecture, build-versus-buy decisions on models and vendors, and one scoped pilot with success criteria signed off by its executive owner.

Deliver · Weeks 4–10

The pilot ships to real users behind evaluation gates, and its impact is reported against the baseline every week.

Scale · Ongoing

The platform, playbooks, and hiring plan that let your team repeat the result across products without me.

For investors

How I evaluate an AI company

The questions I bring to technical due diligence — from someone who has raised capital, built the platforms, and hired the teams.

Defensibility

What remains valuable when frontier models improve next quarter: proprietary data, workflow depth, distribution.

Architecture

Whether the system can scale in users, tenants, and use cases without a rewrite — and where the debt sits.

Evaluation rigor

How quality is measured and gated before release. Teams without evals are shipping demos.

Unit economics

Inference, retrieval, and human-review cost per outcome, and how it trends as usage grows.

Enterprise readiness

Security, tenant isolation, compliance, and private deployment — what large customers will demand in procurement.

Team

Whether the technical leadership can hire, ship, and make sound build-versus-buy decisions at the next stage.

Results

Outcomes I have delivered

Selected results from leadership roles. Further detail is available on request.

Eightfold AI

One agent platform for every product line

Challenge
Multiple product lines needed AI agents with memory, tool access, and enterprise-grade isolation, without each building its own stack.
Result
Architected a shared agent platform — runtime, authoring, memory, tool access, guardrails, and evaluation — and took three agentic products from first code to production on it.
3 agentic products shipped
Walmart Global Tech

Semantic search for Walmart.com

Challenge
Long-tail shopping queries were poorly understood, and search ran on a costly legacy Oracle Endeca stack.
Result
Founded the Query Understanding team — entity extraction, intent classification, query rewriting — and led the Endeca replacement across a 100+ engineer organization.
+85% long-tail · −13% infra cost
MarkovML

An enterprise AI platform, built from zero

Challenge
Defense and EdTech customers required private, compliant AI over proprietary data.
Result
Delivered model routing, retrieval, fine-tuning, inference, and agent workflows on multi-tenant infrastructure certified to SOC 2 Type II.
Deployment: 1 week → hours
Amazon Alexa AI

Higher quality at lower cost to serve

Challenge
Open-domain conversations needed to improve without increasing serving cost.
Result
Redesigned generation, retrieval, relevance, and safety systems, with a new evaluation process gating every model change.
2× satisfaction, −15% cost
Working together

Who I work with

I keep a small roster so that every client receives senior attention.

A strong fit if…

  • An executive sponsor and a business number AI must move — revenue, margin, or cost to serve
  • You want to own your platform and capability, not rent them from a vendor
  • You need counsel that holds up in the boardroom and in an architecture review
  • You will measure the result against a baseline

Likely not a fit if…

  • Your core problem is computer vision or time-series forecasting — my focus is language, search, and agents
  • You need a strategy document rather than results
  • You are seeking hourly staff augmentation
Principles

What you can count on

Independent

No vendor referral fees or reseller arrangements. Recommendations serve your interests alone.

Confidential

Under NDA from the first substantive conversation. Client work is never shared without permission.

Senior and hands-on

You work with me directly, from the first assessment to production. No hand-offs to junior staff.

Accountable

Success criteria agreed up front with an executive owner, and progress reported against a baseline.

I have spent 15+ years building AI that real people use — and the last decade leading the teams and companies that build it.

As Head of AI & Engineering at Eightfold AI, I lead four product lines and 50+ engineers. I architected the shared platform our agents run on and took three agentic products to production — agents that work for weeks alongside people, assistants with long-term memory, and analytics that answer leaders’ questions in plain language. As co-founder and CPTO of MarkovML, I raised $8M, built a 35-person company, and delivered an enterprise AI platform to SOC 2 Type II. Before that I led conversational AI at Amazon Alexa, founded the Query Understanding team behind Walmart.com search, and was the second engineer on eBay’s machine translation engine.

I work with CEOs and boards on where to invest, with CTOs on how to build, with founders on becoming enterprise-ready, and with investors on which AI companies will last.

Experience

Career

Full history on LinkedIn

2025 — Present

Head of AI & Engineering

Eightfold AI

Member of the extended leadership team, reporting to the CTO. Lead four product lines and 50+ engineers across the U.S. and India, with ownership of headcount, budget, and vendor spend. Architected the shared agent platform — runtime, authoring, memory, tool access, guardrails, and evaluation — and took three agentic products from first code to production, spanning long-horizon hiring agents, career guidance, and conversational workforce analytics. Made AI-assisted engineering standard practice across every team.

2021 — 2025

Co-Founder & CPTO

MarkovML

Led a 35-person company with engineering, platform, security, and go-to-market reporting in. Raised $8M, sold into defense and EdTech, achieved SOC 2 Type II, and presented strategy and risk to the board. Merged in 2025.

2020 — 2021

ML Lead, Conversational AI

Amazon Alexa AI

Doubled user satisfaction and reduced cost to serve by ~15%. Delivered the evaluation system that gated every model change before production.

2018 — 2020

Co-Founder & CEO

Ingenus

Raised pre-seed funding and launched a multimodal conversational shopping assistant. Wound down when COVID closed retail, returning remaining capital to investors.

2015 — 2018

ML Architect, Search Science

Walmart Global Tech

Founded the Query Understanding team behind Walmart.com semantic search, improving long-tail understanding by 85%. Led the replacement of Oracle Endeca across a 100+ engineer organization, reducing infrastructure cost ~13%.

2009 — 2015

ML/NLP Engineer → Tech Lead

eBay · Microsoft · AMD

Second engineer on eBay’s machine translation engine ($1B+ added GMV); Office for Mac storage; production software for AMD’s APU line.

FAQ

Common questions

How does an engagement begin?

With a 30-minute conversation about the outcome you need. If there is a fit, you receive a one-page proposal with objectives, measures of success, and scope within 48 hours. Most clients begin with the two-week AI Value Diagnostic.

Do you advise, or also execute?

Both. I brief executives and boards, and I review architecture and work directly with engineering teams to see recommendations through to production.

How do you handle confidentiality?

Every engagement is covered by an NDA. Client names and details are never published without written permission.

Are you independent of vendors?

Yes. I accept no referral fees or commissions from model, cloud, or software vendors. I work across frontier, open-source, and private models on AWS, GCP, or Azure.

Do you work with venture investors?

Yes. I run technical due diligence on AI companies for funds, advise portfolio companies on architecture, hiring, and enterprise readiness, and take a small number of advisory and board roles.

How does this fit with your role at Eightfold AI?

I take on a small number of advisory engagements that do not conflict with my role at Eightfold AI, and I decline work for companies that compete with it.

How many clients do you take on?

A small number at a time, so each engagement receives senior attention. Early contact is recommended if you have a deadline.

Contact

Let's talk about what you're building — or backing.

Whether you lead a company, an engineering organization, or a fund, share what you are working on. I respond within two business days.

or email pankaj@pankajrajan.com