360° Professional Profile

Web Griebel

Payments Executive  ·  Fintech Leader  ·  AI Commerce Pioneer

WooCommerce · Automattic Global Payments Heartland 20 Years Leadership
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Meet Web

A 60-Second Introduction

An AI-generated overview of who I am, how I lead, and what drives me.

Commercial Impact

Results That Move the Needle

Consistent, measurable outcomes across multi-billion dollar payment businesses spanning ecommerce, ISV, and enterprise channels.

19%
Revenue Growth
YoY at WooCommerce in 2025
27%
TPV Acceleration
WooPayments total processing volume YoY
~$35B
TPV Managed
Monetization take rates improved ~25%
$400M+
P&L Exceeded
Global Payments online payments, ~90% NOI
~$500M
ISV Partnership Book
Strategic ISV partnerships business led
35–40%
YoY Growth
Global Payments online & mobile payments
Career Journey

20 Years of Fintech Leadership

From commercializing early mobile payments to leading global P&L strategy for millions of merchants worldwide — a through-line of outcomes at scale.

October 2024 – Present
WooCommerce / Automattic
VP — Commercial Lead, Payments (interim GM)
  • Grew global fintech/payments revenue by ~$21M (19%) in 2025 through rigorous GTM execution and P&L management
  • Accelerated WooPayments TPV by 27% and Cash Sales by 26% YoY by optimizing distribution and retention
  • Drove a 16% YoY increase in payment partners' Cash Sales by renegotiating key strategic fintech alliances
  • Elevated team AI proficiency by deploying Claude CoWork agents across UX, security, and business functions
  • Oversight of BD & partner management, technical account management, and payments/fraud/risk operations
Interim GM Global P&L AI Deployment Team of Teams
August 2022 – October 2024
WooCommerce / Automattic
Head of Payment Partnerships & BD
  • Spearheaded the fintech partner revenue practice serving millions of global online stores
  • Improved monetization take rates on ~$35B in TPV by ~25% through rigorous strategic negotiations
  • Negotiated key partnerships with Stripe, PayPal, Square, Visa, Mastercard, Mollie, AmazonPay, Airwallex, Elavon, Klarna, Affirm and AfterPay/CashApp
  • Built scalable contracting and onboarding processes that reduced time-to-revenue for new fintech alliances
~$35B TPV Global Partnerships Revenue Practice
January 2020 – August 2022
Global Payments Inc.
Sr. Director, Product — Online Payments
  • Achieved 35–40% YoY growth, exceeding ~$400M revenue target with ~90% net operating income
  • Owned P&L and product vision for a comprehensive suite: B2B, e-commerce, and PayFac solutions
  • Aligned cross-functional leadership across marketing, sales, legal, and finance to execute distribution plans
  • Bridged product capabilities with commercial needs via technical account management and sales engineering
$400M+ P&L 35–40% YoY Product Strategy
May 2018 – January 2020
Global Payments / Heartland
Sr. Director, Strategic Partnerships
  • Led the ~$500M ISV partnership business strategy and GTM for integrated software payments
  • Integrated multi-channel ISVs across hospitality, B2B/billing, e-Commerce, ERPs, and CRMs
  • Leveraged economic levers to drive mutual growth and bolster market footprint in high-growth vertical SaaS
~$500M ISV Book Integrated Payments
September 2015 – April 2018
Global Payments / Heartland
Director, Business Development
  • Drove revenue-growth partnerships with banks, ISVs, industry associations, CPA firms, and e-commerce providers
  • Deployed flexible, secure online/mobile payment options across multiple digital solution channels
January 2013 – August 2015
Heartland Payment Systems
Product Integration Lead
  • Commercialized Developer Portal & SDKs, Apple Pay, and Google Pay for hospitality and retail markets
  • Managed large-scale rollout of mobile and online ordering solutions, overseeing pilot programs that validated product-market fit
2002 – 2012
Early Career, Entrepreneurial & Advisory Roles
Multiple NYC-based leadership, startup, and sales management roles
  • Heartland Payment Systems — Senior Sales Leader (2004–2010)
  • BigMix Events LLC — Founder & Operator, NYC (2007–2010)
  • Kindling LLC — Innovation Sales Consultant, NYC Startup (2010–2011)
  • Stephen-Bradford Search — Director, Technology Practice (2011–2012)
  • Rewards Network / IncentOne — Sales Management Roles (2002–2004)
Leadership Profile

How I Lead & Operate

Insights synthesized across four formal assessments: Enneagram iEQ9, Axiogenics VQ Self-Leadership, DISC/Values, and an integrated personality profile.

DISC / Values
Automattic Coaching Report
Dominance (D)High
Conscientiousness (C)High
Influence (I)Moderate-High
Steadiness (S)Moderate-High

High D/C profile: results-driven, analytical, and systematic. Leads with authority and precision. Drives toward outcomes with strategic rigor and high standards.

Enneagram iEQ9
Integrative Enneagram Report
8
The Challenger
Protective  ·  Decisive  ·  Resilient

Natural protector and strategic challenger. Leads with conviction, advocates for fairness, and creates space for others to thrive — while maintaining high standards and driving toward meaningful, lasting impact.

Axiogenics VQ
Self-Leadership Report
Systemic (Structure / Role)High
Extrinsic (Commercial)High
Intrinsic (People)Moderate-High

Motivated by structured achievement and commercial outcomes. Strong people orientation balanced by pragmatic execution. Highest satisfaction in roles with clear authority and meaningful ownership.

Personality Profile
Integrated Assessment
"Psychologically healthy, resilient, and highly achievement-oriented. Strong executive orientation combined with emotional stability and a collaborative, protective leadership style."

Primary developmental challenge: ensuring alignment between capability, authority, purpose, and opportunity. Thrives in autonomous, high-stakes roles with real ownership.

Primary Strengths
Strategic systems thinking
Emotional stability & resilience under pressure
High accountability and follow-through
Comfort with ambiguity in complex environments
Strong leadership presence and executive credibility
Ability to inspire trust and long-term stability
Balanced realism and genuine empathy
HIGH5 Strengths
1
Coach
Develops others to their full potential
2
Philomath
Deep love of learning and knowledge acquisition
3
Self-Believer
Strong inner confidence and conviction
4
Believer
Driven by core values and sense of purpose
5
Deliverer
Committed to executing and following through
Integrated Archetype
"A strategic, resilient achiever-leader driven by autonomy, impact, fairness, and meaningful accomplishment."
Synthesized across Enneagram iEQ9, Axiogenics VQ, DISC/Values, and broader personality assessments
360° Perspective

Working With Web

Synthesized themes from peer, manager, and direct report feedback records across multi-year tenure at Automattic/WooCommerce and Global Payments.

"Web brings both strategic clarity and commercial intensity to every initiative — he sees the whole board and plays to win, while bringing the team with him."
Strategic Vision & Commercial Drive
"He has a rare ability to translate complex fintech concepts into compelling narratives that move partners, stakeholders, and leadership teams to act."
Communication & Influence
"When the pressure is highest, Web becomes more focused — not less. His calm under fire gives the team confidence that we'll find a path through."
Resilience Under Pressure
"He raises the bar for everyone around him. His standards are high but fair — and he's genuinely invested in the development and growth of his team."
People Development & Leadership
"Web builds trust with external partners quickly — they feel like he understands their business deeply, not just his own agenda. That's rare in BD."
Partnership & Relationship Building
"He holds people accountable in a direct, respectful way. You always know where you stand — no ambiguity, no games. That clarity is actually motivating."
Accountability & Directness
"Web made our team measurably better at using AI — from workflow automation to agent deployment. He doesn't just talk about AI adoption; he ships it."
Innovation & AI Enablement
"Impatience with organizational drag can surface when he sees a clear path forward and process is slowing things down — an energy worth channeling strategically."
Development Area: Pacing & Process
AI Literacy

Commerce in the Age of AI

Practical, deployed expertise in AI protocols, tools, and commercial applications — built from first-principles usage and hands-on production deployment.

OpenAI / Stripe ACP
Agentic Commerce Protocol enables AI agents to autonomously complete commercial transactions. Deep commercial narrative on how ACP rewrites payment workflows — from discovery to settlement — without human intervention, and what that means for merchant acquisition and PSP strategy.
Agentic Commerce
🌐
Google UCP
Universal Commerce Protocol positions Google's AI infrastructure as a universal commerce layer. First-mover perspective on how UCP reshapes search-to-checkout experiences, displaces traditional payment routing, and creates new distribution levers for merchants and PSPs alike.
Universal Commerce
🔗
MCP Servers
Model Context Protocol connects AI agents to business systems, APIs, and data sources. Hands-on deployment of MCP servers to automate payment operations, fraud review workflows, partner reporting, and commercial intelligence pipelines at WooCommerce.
Agent Infrastructure
🤖
Claude CoWork & Claude Code
Deployed Claude CoWork and Claude Code to build and ship agents that augment UX, security, and commercial functions across WooCommerce's payments practice. Elevated team AI proficiency at scale, moving from theoretical AI interest to production deployment.
Production Deployment
💬
ChatGPT & Gemini
Daily practitioner of OpenAI ChatGPT and Google Gemini for strategic analysis, competitive intelligence, partner briefings, commercial planning, and workflow acceleration. Certified in Prompt Engineering via Vanderbilt University. Understands model capability trade-offs at a commercial level.
AI Productivity
🛒
Agentic Commerce Vision
The next frontier of fintech: AI agents discovering, evaluating, and completing purchases autonomously. This rewrites merchant acquisition, payment orchestration, and fraud logic — and Web brings a first-principles commercial narrative for where the market goes next and how to position ahead of it.
Strategic Narrative
Digital Finance & Payments

The Future of Money Movement

From global payment rails to digital currencies and cross-border financial infrastructure — a 360° command of the modern payments ecosystem built across two decades.

💳

Digital Wallets

Deep hands-on experience with Apple Pay, Google Pay, PayPal, AmazonPay, AliPay, WeChat Pay, GrabPay, and emerging wallet-as-a-service infrastructure. Strong understanding of tokenization, biometric authentication, and the shift toward wallet-native and device-native commerce experiences. Positioned WooPayments' strategy to capitalize on wallet-led checkout conversion improvements globally.

Digital Currencies & Stablecoins

Certified in Cryptocurrency & Blockchain: Introduction to Digital Currencies. Commercial perspective on stablecoin adoption for B2B settlement (USDC/USDT), their role in reducing FX conversion friction, and how Central Bank Digital Currencies (CBDCs) are beginning to reshape the correspondent banking model. Tracks regulatory evolution of digital currency frameworks across key markets.

🌍

Cross-Border Money Movement

Practical experience optimizing international payment experiences for millions of global merchants across WooCommerce's distributed merchant base. Deep familiarity with FX conversion economics, multi-currency settlement, compliance-aware routing, and the operational dynamics of cross-border transactions via partners including Airwallex, Mollie, and Stripe. Understands where the friction lives — and how to reduce it commercially.

Payments Ecosystem Command

Global Payment Methods
Card NetworksPayPalAliPayWeChat PayGrabPayBNPLsPIXUPIiDEALSwishGiropay/SofortBlikACHRTPFedNow
PSP & Partner Ecosystem
StripePayPalVenmoSquareVisaMastercardMollieAmazonPayAirwallexRevolutElavonKlarnaAffirmAfterPay/CashAppBlikP24
Fintech Product Domains
Payment OrchestrationEmbedded FinanceCard IssuingRisk & FraudTokenizationPayFaceCommerceB2B/RecurringIntegrated PaymentsMobile PaymentsWeb3/BlockchainStablecoins
Industry Verticals
Retail (POS & Digital)HospitalityRestaurant & EventsB2B SaaSeCommerceLodgingServicesISV / SoftwareOmni-ChannelMobile Commerce
Credentials

Education & Certifications

🎓
University of Delaware
B.S. Human Resources — HRIM
Heavyweight Varsity Eight Crew
🤖
Prompt Engineering for ChatGPT
Vanderbilt University
Cryptocurrency & Blockchain
Introduction to Digital Currencies
💰
Fintech: Foundations & Applications
Financial Technology Certification
📋
Pragmatic Management Certified
PMC-V
HIGH5 Strengths Assessment
Coach · Philomath · Self-Believer
+ Believer · Deliverer