Gagan
Maheshwari
Fintech & Payments Product Leader
I build and ship products, platforms, and high-stakes workflows where trust is the feature. I’m strongest where strategy meets execution: translating a direction into alignment, governance, and measurable outcomes.
The pattern I've seen at scale
Most fintechs don’t lose on ideas. They lose when decision-making, risk ownership, and platform truth stop scaling.
Compliance bottlenecks, platform debt, unclear ownership, and misaligned incentives kill more products than bad ideas ever will.
At PayPal scale and in fast-moving teams alike, mistakes are expensive: customer harm, regulatory exposure, and margin drag.
The job stays the same: ship outcomes without breaking trust.
Scale context
Coverage and credentials across payments and regulated systems.
How I lead
Principles I use to create clarity, alignment, and predictable shipping outcomes in regulated environments.
Strategy built for constraints
I anchor decisions in customer truth, unit economics, and real constraints across risk, legal, and ops. If a plan can’t run inside those constraints, it isn’t a strategy yet.
Anti-pattern: Vision without viability
Alignment is a deliverable
In regulated fintech, product doesn't 'hand off' to risk. I define a common language for what 'safe to ship' means, and make it shared across product, engineering, legal, and sales.
Anti-pattern: Handoff without alignment
Evidence over persuasion
I set the metrics early and instrument the funnel. Narrative follows the numbers. This approach improved checkout and activation and helped drive 700k+ new users.
Anti-pattern: Slides over data
Platform work must earn its keep
Modernization is not a multi-year permission slip. I define milestones that show up as feature velocity, reliability, and reduced risk, not just architecture diagrams.
Anti-pattern: Multi-year modernization
AI is leverage, not identity
AI matters when it improves outcomes with controls: monitoring, escalation paths, clear ownership, and measurable impact. Otherwise it’s distraction. I validate agentic workflows against compliance reality before building.
Anti-pattern: AI as identity
My operating model
How I run product so strategy turns into shipped outcomes predictably, measurably, and transparently.
Portfolio clarity
A small number of bets, explicitly sequenced. No hidden work.
Portfolio clarity
A small number of bets, explicitly sequenced. No hidden work.
Governance
Clear owners, decision logs, and launch criteria. No ambiguity.
Cadence
Weekly execution review, monthly strategy check, quarterly portfolio reset.
Talent
Role clarity, high standards, fast feedback loops, and accountability.
Narrative
Concise tradeoffs and clear choices, not long decks.
Experience highlights
Orlaya & Advisory
Interim Executive / Strategic Advisor
Work with Series B/C Fintechs and Fortune 500 enterprises to bridge the gap between strategy, execution and velocity.
Highlight: Turnaround and scale work: tightening the product system so teams move faster with fewer surprises.
PayPal
Global Product Leadership (~8 Years)
Led strategy and execution across embedded finance and core platforms, including a $50M+ revenue opportunity and products serving 300M+ users.
Highlight: Built and shipped 0→1 initiatives inside the enterprise using small cross-functional teams and tight operating cadence.
Equinix / IBM / ADP
Enterprise Platforms
Built systems where latency, uptime, security controls, and integration reality defined the user experience.
Highlight: Shipped API and platform capabilities that held up under audit, load, and enterprise change control.
What I’m focused on now
The messy middle of fintech scale: trust, platforms, and AI under constraint.
Scaling regulated platforms without stalling innovation
Rebuilding trust between product, engineering, risk, compliance/legal and sales
Modernizing critical infrastructure without multi-year paralysis
Applying AI only where controls + measurement exist from day one
"If you want the real signal, don’t look for slogans. Look at how I think, how I operate, and what I’ve shipped."
Check out latest insightsConnect
If you’re building or investing in payments, platforms, or regulated AI, I’m open to a high-signal conversation.