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Gagan  Maheshwari

Product Strategy and Leadership for Payments at Scale.

Former PayPal product leader. 25 years in regulated systems, 12+ in payments. Sharing the operating reality of scaling payment products, risk constraints, and AI that ships.

I partner with fintechs to build products that scale, leverage AI where it makes sense, and ship faster without breaking trust.

Trusted Experience at Scale

Gagan Maheshwari
The Hard Part

The Scale Paradox

Why do so many Fintechs stall?

Because the traits that got them there (speed, hacks, shortcuts) become the traits that kill them. The hard part is not building fast, it's building fast without breaking trust.

01

The Compliance Wall

Diagnosis

Risk teams block innovation because there is no shared framework for 'safe experimentation' in regulated flows.

02

The 'Platform' Trap

Diagnosis

Engineering rewrites the same infrastructure for years while the business waits for features that never ship.

03

The AI Distraction

Diagnosis

Teams chase shiny AI demos while their core ledger integrity and reconciliation processes are crumbling.

How I run product (short version)

Three moves that restore velocity without breaking trust.

Strategy built for constraints

Customer truth, unit economics, and real constraints up front.

Clear bets, explicit tradeoffs, measurable outcomes.

“Safe to ship” is defined, not implied

Shared launch criteria across Product, Eng, Risk/Legal, and Ops.

No late-stage vetoes. No hidden owners.

Cadence and governance that holds up

Scorecards, decision logs, and feedback loops that keep delivery predictable.

Execution compounds when the system is stable.

Impact across payments

A few outcomes from payments, risk, and platform modernization, where scale and constraints were non-negotiable.

Embedded Finance Platform

$50M+ revenue opportunity

Led the platform unlocking embedded payments for partners, designed to scale through risk and compliance constraints.

Checkout and Activation

>700K+ Users

Orchestrated a cross-functional strategy improving conversion and activation through rigorous funnel instrumentation.

Platform Resilience and Reliability

-20% Latency

Overhauled critical payment infrastructure, reducing incidents and improving merchant trust in high-stakes environments.

Impact at a glance

Selected outcomes across shipped initiatives in payments and regulated platforms.

$1B+TPV influenced (across initiatives)
300M+Customers Served
>700KNet new actives influenced (checkout and activation)
$50M+Revenue opportunity (embedded finance platform)

Ways to work together

I take on a small number of roles and engagements where strategy, scale, platform debt, or regulated AI is blocking growth.

Most Requested

Interim Product Leadership

I step in as CPO or VP Product to stabilize the organization, reset strategy, and drive execution during critical transition periods.

Strategic Product Advisory

I partner with CEOs and Boards to audit product portfolios, de-risk roadmaps, and align engineering velocity with business value.

Product and Platform Due Diligence

I provide technical and product due diligence for investors, specifically assessing platform scalability and team capabilities.