GM Logo
Gagan  Maheshwari

Now booking select 2026 engagements

Regulated Fintech & Payments Platform Leadership

I partner with product and executive teams to make clear calls on what to ship next across payments, risk/compliance, platform modernization, and AI productization. Then operationalize delivery with controls that hold up in production.

Series B–DEnterpriseRegulated PlatformsWorkshops + Keynotes
Gagan Maheshwari speaking at an industry event

5,000+

Professionals Reached

70+

Speaking Sessions

15+

Global Markets Reached

Metrics reflect prior sessions delivered across product leadership, platforms, and regulated AI education.

Speaker overview

I’ve spent most of my career where software, money, and operations intersect—shipping regulated platforms and high-stakes workflows.

My talks are designed for leaders who already know the stakes and want a grounded way to decide what to do next. Less “future of everything.” More “what should we do in the next 12–24 months given our constraints.”

"Operator-first, systems thinking. No hype."

Current role

Founder, Orlaya

Previous

Product Leader, PayPal

Focus areas

FinTech, payments, onboarding, risk, platforms

Work style

Operator-first, systems thinking. No hype.

Talks are for

Execs who need to decide what to do next. Not just be inspired.

Formats

Pick the format based on what you actually need: clarity, alignment, or an execution plan your teams can run next week.

Keynote
30–45 minutes

What they get

  • A decision framework leaders can reuse
  • The failure modes that kill regulated velocity
  • What 'safe to ship' looks like in the real world

Best For

Conferences, leadership offsites, company all-hands

Size: 50–5,000
Panel / Fireside
30–60 minutes

What they get

  • Clear, non-performative answers to AI/Platform questions
  • Practical tradeoffs (risk, ops, velocity)
  • Grounded examples without leaking confidential internals

Best For

Fintech + platform summits, executive roundtables

Size: 50–500
Executive Briefing
60 minutes

What they get

  • Decision-ready framing (tradeoffs + constraints)
  • What to measure and report to avoid AI theater
  • A prioritized next-steps memo (optional add-on)

Best For

C-suite/board education, PE/VC portfolio leadership sessions

Size: 6–25
Workshop (Working Session)
90 minutes to full day

What they get

  • A shared definition of 'safe to ship'
  • A scorecard + cadence to restore predictability
  • A sequenced plan tied to measurable outcomes

Best For

Cross-functional teams (Product + Eng + Risk/Legal + Ops)

Size: 12–40

Keynote & Panel Topics

Key Takeaways

  • The Compliance Wall and how to create 'safe experimentation' instead of gridlock
  • The Platform Trap: modernization that earns its keep (milestones tied to velocity + reliability)
  • A shared language for Product, Engineering, Risk/Legal, and Ops
  • The minimum operating system: scorecard, cadence, governance

Ideal Audience

Product leadership offsites, fintech conferences, platform + risk summits

Formats

KeynotePanelExecutive BriefingWorkshop

Key Takeaways

  • Where agentic workflows help in payments, risk, onboarding, and support—and where rules/humans still win
  • Guardrails that matter: audit trails, rollback paths, human-in-the-loop, ownership
  • Practical criteria for choosing first (or next) workflows
  • What ‘safe to ship’ looks like when outcomes are uncertain

Ideal Audience

Fintech product teams, executive strategy sessions, applied AI leadership audiences

Formats

KeynotePanelWorkshop

Key Takeaways

  • How to frame AI in terms boards actually care about (risk, margin, time-to-value)
  • Avoiding both under- and over-promising on timelines and impact
  • What to measure and report when outcomes are still uncertain
  • Using small, well-designed pilots to buy time and credibility

Ideal Audience

Board retreats, C-suite summits, PE/VC portfolio leadership sessions

Formats

Executive BriefingPanel

Key Takeaways

  • Why systems (not features) determine outcomes in regulated environments
  • How platforms, APIs, and teams interact with AI initiatives
  • Common failure modes when retrofitting AI onto legacy systems
  • How to keep architecture, risk, and product aligned on what to ship and when

Ideal Audience

SaaS/platform conferences, internal product + architecture summits

Formats

KeynotePanelWorkshop

Workshop moments

A few snapshots from workshops and leadership sessions.

Keynote on API strategy for digital transformation

Keynote on API strategy for digital transformation

Workshop on governance model and design

Workshop on governance model and design

Group picture after a successful full day workshop for product and technology leaders

Group picture after a successful full day workshop for product and technology leaders

Speaking inquiry

Limited availability for 2026 executive and product-focused events. Share context and constraints and I'll respond with fit and next steps.

Tip: Please include estimated date, audience profile, and desired outcomes.

Speaking Inquiry