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About

Rakesh Kamath

The short version

I've spent 20+ years doing one thing in different contexts: walking into companies where the traction is real but the systems are fragile, and installing the engineering, operational, and financial infrastructure that makes growth durable.

That's it. That's the whole thing.

The companies change. The industries change. The tech stacks change. (Remember when everyone needed a Flash developer? I was that guy. In Bangkok, no less.) But the pattern stays the same. Something is working. Something is also breaking. And nobody has connected the systems that would let the working part scale without the breaking part getting worse.

I fix the connection.

The pattern

Every company I've worked with, whether I co-founded it, led the engineering org, or walked in as an advisor, has followed the same arc. The specifics are different. The structure of the problem never is.

The Durable Growth Arc

Diagnose

Find the structural weakness (not the symptom everyone is complaining about)

Install cadence

OKRs, planning rhythm, delivery metrics, ownership clarity

Align to revenue

Wire engineering output to business outcomes

Modernize the platform

Cloud-native, event-driven, integration-ready

Strengthen governance

Compliance, security, risk controls that unlock markets

Stabilize cash

R&D credits, capital efficiency, runway awareness

Scale durably

Growth that doesn’t collapse when you double

If you're thinking “that sounds obvious,” you're right. It is obvious. It's also almost never done in order, and half of it gets skipped entirely because everyone wants to jump straight to the modernize step. (“Let's rebuild the platform!” No. Let's figure out why you're rebuilding it first.)

The reason this works is boring: it's sequential, it's disciplined, and it treats the company as a system rather than a collection of departments with separate Jira boards.

Where I've done this

I don't have a “typical” career path. I've co-founded companies, led 60-person engineering orgs at Deloitte Fast 500 firms, run digital innovation at a Big Five bank, and spent my first eight years building enterprise software in Bangkok and Toronto. The thread that connects all of it is the pattern above.

An AI-powered EdTech SaaS

Joined as Head of Engineering. Got promoted to COO six months later because the company needed an operator, not just an engineering lead. (This happens to me a lot. I should probably put “will inevitably end up running operations” on my business card.)

The company had a great product and loyal teachers. It did not have an enterprise sales motion, a CRM that anyone trusted, a compliance posture that could survive a district IT review, or a clear picture of its own cash position. The engineering team was talented but disconnected from revenue.

What we installed: RevOps from zero (HubSpot, Apollo, pipeline segmentation, closed-lost recovery across 193 deals). Enterprise integration posture (OneRoster, Clever, SSO, API security). An activation-led GTM engine that hit 91–98% license activation in a market where 65% is considered good. Financial controls that identified a cash runway problem five months earlier than the existing forecasts suggested. R&D tax credit optimization that captured ~$600K/year.

114% ARR growth. A company that went from founder-led to enterprise-ready.

A global EdTech platform (Exited 2022)

Co-founded this one. Built it from literally nothing to 5.8M users across 119 countries and 14,400 schools. Full P&L ownership through 35 major product iterations over seven years.

This is where I learned that building the product is maybe 30% of the job. The other 70% is building the company around the product: the team, the architecture that scales without falling over, the data science practice that didn’t exist before we built it, the compliance posture (GDPR, CCPA) that lets you operate globally, and the partner integrations that turn a product into a platform.

We migrated from a monolith to Kubernetes-based microservices. We built a Partner API platform. I served as Data Protection Officer because at a startup, you wear every hat, including the ones that don’t fit.

Guided the company to a successful acquisition in 2022. The exit was the outcome. The system we built was the product.

An assessment technology company (Deloitte Fast 500)

Led 60+ engineers across development, DevOps, and QA. The company was growing fast, had just acquired another company (One45), and needed to merge two product lines, two engineering cultures, and two tech stacks without everything catching fire.

Restructured the engineering org. Installed OKRs that connected engineering initiatives to revenue outcomes (not “improve code coverage”). Co-developed a three-year engineering and platform strategy. Merged the product lines. Kept the humans happy. (That last part is always the hardest and the least documented.)

The company was recognized on Deloitte’s Fast 500 and Canada’s top growing companies list.

A Big Five bank

This is where I learned that large organizations can move fast when you give them permission. And a budget. And air cover from someone two levels up.

Launched the first responsive, personalized digital sales product for retail banking at a North American bank. 35% sales increase within six months. Led a 50-person cross-functional team across four business lines. Defined the 18-month enterprise digital roadmap covering mobile, CMS, analytics, and digital merchandising.

The bank went from unranked to #2 in the Forrester North American Banking rankings.

The early years (enterprise software)

Eight years on a founding team in Bangkok and Toronto, building multi-platform enterprise process management systems. J2EE architecture, cross-platform development, the kinds of deeply unsexy engineering problems that teach you how software actually works when the abstractions fail.

This is where the architectural intuition got forged. Everything I do now in scaling companies is built on the foundation of those years.

The personal bit

Based in Toronto. Building remotely. Originally from India, via Bangkok, which means I've had strong opinions about both food and timezones for most of my adult life.

Before I co-founded my first company, I spent six months surveying 1,000 K-12 educators across Canada and the United States, with 400 video interviews, trying to understand how technology actually gets used in schools. That research obsession never went away. I still believe the best technology decisions start with understanding the humans who have to live with them.

I'm a member of TrueNorthCTO (a community of 1,000+ Canadian technology leaders) and the Toronto Machine Learning Society, mostly because I enjoy being around people who argue about architecture decisions for fun.

Working together

Through my advisory practice, I work with founders and leadership teams who are scaling and whose systems are starting to crack under the weight of their own success. The work usually looks like fractional CTO leadership, GTM engineering, or operational transformation, depending on what's actually broken. My advisory practice operates as Peepul Tree Products.

If that sounds like your situation, there's a page for that.

More about working together

The condensed version

If you need the traditional format for a recruiting process or a board introduction:

Resume PDF coming soon.

Fair warning: this page is the better version.