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Senior Director · AI & Technology Transformation

Converting Complex Enterprise Challenges Into Scalable, Commercially Viable AI Solutions

Senior Director-level AI and technology transformation leader. As Lead Solution Executive for the AI Shared Practice, served as the pre-sales quarterback for AI-enabled opportunities — guiding pursuits from intake through solution architecture, pricing, SOW development, negotiation, and transition to delivery across Application Modernization, Integration, Agile DevOps, and AI-SDLC.

45+
AI Certifications (IBM, Google, Microsoft)
$100M+
Strategic Portfolio Influenced
7x
President's Club Winner
97+
Courses & Certs Completed
Fortune 500
Clients Served Across Verticals
Jory Pai executive portrait
Scroll to Explore
$100M+
Business Value Delivered
President's Club
312%
Quota Record (2014)
40+
Certifications
20+
Years Experience
500+
Leaders Coached
Why Hire Jory

Three Reasons Recruiters Short-List Him

Bridges Technical Depth & Executive Strategy

Talks COBOL modernization with a CTO and ROI modeling with a CFO — in the same meeting. Most leaders are strong on one side; Jory operates fluently in both.

Delivers Measurable Outcomes, Not Activity

$100M+ in cumulative business value. 25–40% cost reductions. 300% faster time-to-market. Every engagement tied to hard numbers the CFO can verify.

Builds Teams That Perform

500+ leaders coached. 7× President's Club. Leads from the front — in the room for hard conversations, accountable to results, invested in people who outgrow him.

60-Second Intro

Meet Jory In His Own Words

Jory Pai executive intro video
Executive Introduction

A quick, personal overview of Jory's experience, approach, and what he's looking for next.

What Colleagues Are Saying

Voices of Trust

Testimonials from leaders at IBM, Red Hat, TEKsystems Global Services, and Oracle.

"I have known Jory since IBM acquired FileNet when Jory became part of my team of Technical Sales specialists. Jory is a dedicated and talented professional. He is an excellent communicator both internally and externally. I have personally observed Jory work through difficult situations with ease and professionalism. Jory has all the skills necessary to be a strong, empathetic, and motivating leader."
Derick DeleoDirector, Technical Sales — IBMManager at IBM
01 / 14
Executive Profile

Senior Director.
AI Transformation Leader.

Senior Director-level AI and technology transformation leader responsible for converting complex enterprise challenges into scalable, commercially viable AI-enabled solutions. Leads strategic pursuits and transformation programs from executive discovery and qualification through solution architecture, operating-model design, financial modeling, contract development, negotiation, and transition to delivery.

As Lead Solution Executive for the AI Shared Practice, served as the pre-sales quarterback for AI-enabled opportunities across Application Modernization, Integration, Agile DevOps, and AI-SDLC. Designed and leads a shared AI solutioning model — a horizontal layer across all practices — with a single enterprise intake and governance process. Routes opportunities through OWN, CO-SOLUTION, CONSULT, and HANDOFF, defining the One Metric That Matters, acceptance criteria, and value-realization plans while maintaining executive accountability and decision traceability.

Directs cross-functional teams spanning AI, application modernization, cloud, data, integration, Agile/DevOps, managed services, cybersecurity, delivery, legal, privacy, and strategic partners. 20+ years across TEKsystems Global Services, Pega, Red Hat, IBM, and Oracle. 7× President's Club. 312% of quota (2014).

Currently seeking Senior Director / VP roles in AI Transformation, AI Solutions Leadership, Technology Transformation, or Application Modernization.

Application Modernization
Business Technology Strategy
AI & Digital Transformation
Cloud Migration
Enterprise Integration
Agile / DevOps
Executive Stakeholder Alignment
Outcome-Based Consulting
Transformation Impact

Measured Outcomes, Not Just Strategy

$0M+

Annual revenue impact across modernization and transformation initiatives

0+

Enterprise clients supported through strategic discovery, solutioning, and delivery alignment

0%+

Performance above target in solution leadership and growth contribution

$0M

Legacy-to-AWS modernization initiative across 50+ legacy applications

0%

Cost reduction achieved through cloud modernization strategy

0%

Performance improvement through modernization execution

$0M

AI-powered retail transformation initiative

$0M

Revenue impact from AI personalization and digital experience improvements

Leadership Philosophy

Strategy Is Only Valuable
When It Becomes Execution

"Transformation is not about replacing technology. It is about unlocking the next version of the business."

Jory's leadership approach is rooted in clarity, accountability, trust, and measurable outcomes. He bridges the gap between boardroom strategy and delivery reality — helping teams define what matters, simplify complexity, and move with purpose.

Modernize with business value first
Simplify complexity before scaling
Align executives, architects, and delivery teams
Build trust through transparency
Turn strategy into execution
Lead people, not just programs
Measure outcomes, not activity
Career Trajectory

Enterprise Transformation Experience

2022 – Present

TEKsystems Global Services / Allegis Group

Global Services Solution Executive — Application Modernization

✦ $100M+ annual portfolio target · 39%+ GP margin delivered

Application Modernization Intake Lead (NW, Canada, SW, Midwest)Led solutioning across Advisory, Cloud, AI/ML, Agile, DevOpsSOW, MSA, legal flow-downs, pricing and commercial structuringIBM & Red Hat channel partnership managementChannels: AWS, Azure, GCP, ServiceNow, Snowflake, MuleSoft, AdobeVerticals: FinServ, Healthcare, Telecom, Energy, Retail, Media/Gaming
2019 – 2022

Pega Systems

Sr. Solutions Consultant — Insurance & Financial Services

✦ 132% quota · $8.5M regulatory penalty avoided at USAA Bank

Pega Customer Service, Real-Time Decision Hub, Next-Best-ActionTransformed 3.7M annual complaints — 53% faster resolutionLowered member attrition, raised NPS, increased first-call resolutionReenvisioned 19M cases in real-time banking
2017 – 2019

Red Hat / IBM

Sr. Solutions Consultant — Middleware & OpenShift

✦ 121% quota · Walmart $15.2M SYB / $40M total book

OpenShift, Kubernetes, DevOps, cloud-native modernizationBNSF: converted 2 billion API calls to new API management platformAA, Southwest Airlines, SABRE, Pepsi — hackathons, OpenShift daysTIBCO migration, JBPM, BRMS, BPMN, Drools, Kafka, Camel
2015 – 2017

Oracle

Sr. Solutions Consultant — Digital Experiences (DX) Middleware

✦ Business-outcome focused digital transformation

Mobile, Web, IoT, Blockchain, Digital AssistantsECM, WebCenter, AI co-innovation with enterprise clientsCreating compelling user experiences across verticals
2014 – 2015

Jitterbit

Sr. Client Software Solutions Architect — SaaS Integration & API

✦ Cloud/on-prem integrations for enterprise platforms

Autodesk, Adobe, PLM, MS Dynamics, Salesforce, NetSuite, SAPAmazon, Azure, Social Media, Workday, Magento integrationsBuilt trust with key enterprise decision-makers
2010 – 2014

IBM Corp.

Sr. Client Software Solutions Specialist / Architect

✦ ECM, BPM, FileNet, Case Management, eForms

Solution discovery, demos, POC engagements, ROI modelingEvangelized and guided enterprise clients to IBM solutionsConsistently exceeded sales goals — highly ranked nationallyBuilt partner competency and readiness end-to-end
2006 – 2010

IBM / USA Consulting

Sr. Information Technology Specialist → Solutions Architect

✦ IBM FileNet expert · trusted advisor to sales teams & partners

BPM, Enterprise Content Management, Records Management, Case MgtPre-sales workshops, technical education, proof-of-concept deliveryCollaborated with Marketing and Sales to build proactive sales playsEnablement training for cross-functional sales teams
Proven Results

Named Client Wins & Transformations

Real engagements — named clients, real dollars, verified outcomes. Jory served as Solutions Executive or Lead Solutions Architect on each.

Financial Services · Pega

✦ USAA Bank

Real-Time Decision Hub & Customer Service Modernization

132% Quota · Solutions Executive

53%
Faster complaint resolution
$8.5M
Regulatory penalty avoided
3.7M
Annual cases transformed

Implemented Pega Customer Service and Next-Best-Action across Bank, P&C, and Life. Lowered member attrition, raised NPS, increased first-call resolution. Reenvisioned 19M cases in real-time banking.

Retail & Transportation · Red Hat

✦ Walmart & BNSF Railway

IT Cost Reduction, API Modernization & IoT at Scale

121% Quota · Solutions Consultant

$15.2M
Walmart SYB
2B+
API calls migrated (BNSF)
$40M
Total book of business

Led cloud-native modernization for Walmart including DevOps, eCommerce growth (8–10% online), and emerging tech. BNSF: converted 2 billion API calls to new API management, deployed IoT sensors, iBPMS.

Retail · TEKsystems Global Services

✦ Starbucks Corporation

Next-Gen POS Platform — NGCommerce App Dev

$6M Net New Win · Solutions Executive

$6M
Net new engagement
3
Platform workstreams
2026
Store 0 target go-live

Jory served as Solution Executive for a $6M net new win at Starbucks to build their in-house next-gen point-of-sale platform (NGCommerce), replacing Oracle Simphony and rewiring Order Capture, Order Management, and Store State. Success measured by barista NPS.

Energy · TEKsystems Global Services

✦ Southern Company Gas

Maximo Implementation — Project Matrix

$3.4M Renewal · Solutions Executive

$3.4M
Engagement value
2028
Potential extension

Jory served as Solution Executive when Southern Company Gas brought their Maximo + GIS implementation in-house from EY, selecting TEKsystems as their trusted capacity partner for Project Matrix. Immediate start, multi-year extension potential.

Financial Services · Appian UAT

✦ Santander Bank, N.A.

UAT Testing Appian — CSAT: Exceeded Expectations

NPS Promoter · Solution Executive

100%
Engagement success
Promoter
NPS reference
Exceeded
CSAT rating

Named Solution Executive on the Santander Bank engagement. Client praised strategic alignment, responsive communication, and seamless resource transition management. CSAT results: Successful, Exceeded Expectations, NPS Promoter — no improvement notes.

Energy · TEKsystems Global Services

✦ Occidental Petroleum (Oxy)

AI Center of Excellence Partnership

Strategic E2E Win · Published Win Story

ACE
AI Center of Excellence
E2E
Sales process win

Featured in a published TEKsystems win story. Strategic E2E pursuit engaging Oxy's AI Center of Excellence innovation lead. Multi-week sequencing strategy led to a pivotal partnership in AI-driven modernization.

Previous Role · Lead Solution Executive, AI Shared Practice

The Pre-Sales Quarterback for AI-Enabled Opportunities

Application Modernization · Integration · Agile DevOps · AI-SDLC

Served as the executive solutioning lead and pre-sales quarterback for AI-enabled opportunities — guiding pursuits from intake and qualification through discovery, solution strategy, architecture alignment, estimation, pricing, proposal and SOW development, negotiation, and transition to Delivery. Connected the AI Shared Practice with Sales, Application Modernization, Cloud, Data, Integration, Agile/DevOps, industry practices, partners, and Delivery — determining whether the practice should OWN, CO-SOLUTION, CONSULT, or HANDOFF each opportunity.

Single Front Door

One enterprise intake and governance process for every AI opportunity across all practices.

Four Routing Outcomes

OWN, CO-SOLUTION, CONSULT, and HANDOFF — defined ownership with executive accountability.

Responsible AI Controls

Data governance, security, privacy, IP, human oversight, model evaluation, observability, and vendor risk.

Decision Traceability

Every handoff, approval, and value claim recorded — from discovery through transition to delivery.

Solution Integrity

Owns solution integrity, scope, assumptions, estimates, pricing, margin alignment, proposals, SOWs, and executive presentations. Defines the One Metric That Matters, baseline, target outcomes, acceptance criteria, and value-realization approach. Protects solution and commercial integrity through proposal development and negotiation.

Cross-Functional Direction

Assembles and leads cross-practice pursuit teams — architects, delivery leaders, SMEs, proposal resources, partners, and control functions. Obtains Practice and Delivery approval before client commitments, and leads the formal transition to Delivery with an accepted solution, commitments, risks, and measurement plan.

Responsible & Operational AI

Ensures AI solutions address data, security, privacy, intellectual property, responsible AI, human oversight, evaluation, observability, and operational risks. Maintains opportunity quality and traceability in Connected/Salesforce — Value Framework, Solutioning Checklist, approvals, risks, decisions, and supporting evidence.

Executive-level purpose: Build a repeatable, governed, and commercially effective solutioning capability that converts AI demand into qualified opportunities, differentiated solutions, executable engagements, measurable customer outcomes, and scalable revenue for the AI Shared Practice.

Practice Deliverables

(6 artifacts · downloadable)
DOCX

Solution Executive Solutioning Process

Deal capture, decision gates, controls, and transition standard. Proposed operating model aligned to the existing TGS Solutioning lifecycle — preserving controls that work while adding AI-specific evidence and risk disciplines.

Sep 2026 View
DOCX

Solution Intake & Routing Operating Model

A scalable, auditable operating system for qualifying, routing, solutioning, and measuring enterprise AI opportunities. Establishes whether an opportunity is truly AI-led, which practice is accountable, who must participate, and what evidence is required.

Sep 2026 View
HTML

AI Shared Practice Report

Executive report on the AI Shared Practice operating model, governance framework, and portfolio analytics — designed for leadership review and pilot rollout.

Sep 2026 View
DOCX

Claude Enterprise Solutions Seller Playbook

How to identify, position, qualify, and expand enterprise transformation opportunities using Claude with AWS, Microsoft Azure, Google Cloud, and Red Hat. The core equation: Business Problem × Claude Intelligence × Customer Platform × TGS Delivery = Measurable Enterprise Outcome.

Aug 2026 View
DOCX

Seller Playbook v2 — Anthropic-Aligned

Anthropic-aligned edition mapping TGS solution plays to the official 13-service Anthropic Claude taxonomy across the full lifecycle: Assess & Plan → Prove & Build → Activate & Adopt → Operate & Optimize. Includes seller signals, land-and-expand pathways, and discovery guidance.

Aug 2026 View
DOCX

TGS + Google Cloud + Anthropic Strategic Brief

Strategic go-to-market brief for building the AI-Native Enterprise through application modernization, agentic engineering, and industry solutions. Combines the established Google Cloud relationship, the expanded Anthropic partnership, and full-stack modernization into a repeatable enterprise AI proposition.

Aug 2026 View
Core Capabilities

Where Strategy Meets Modernization

Application Modernization

Legacy assessment, cloud migration, platform modernization, technical debt reduction, scalable architecture.

Business Technology Strategy

Aligning enterprise technology investments with business outcomes, growth priorities, and operational transformation.

AI & Intelligent Automation

Using AI, automation, and data-driven workflows to improve productivity, customer experience, and business performance.

Cloud & Platform Strategy

Cloud-native modernization, OpenShift, Kubernetes, AWS, Azure, GCP, hybrid cloud, and platform operating models.

Agile, DevOps & Delivery Acceleration

Improving execution speed, quality, collaboration, release cycles, and engineering culture.

Enterprise Integration

API strategy, microservices, system connectivity, legacy integration, and digital ecosystem modernization.

Executive Solutioning

Discovery, stakeholder alignment, SOW creation, pricing, roadmap development, and value-based consulting.

Skills Matrix

Technical Depth, Quantified

Proficiency levels across the six pillars that define Jory's expertise — for quick keyword matching and capability assessment.

Cloud Platforms

Expert
95%
AWSMicrosoft AzureGoogle Cloud (GCP)Red Hat OpenShiftIBM Cloud

AI & Data

Advanced
88%
AI Strategy & AdoptionGCP Google AIMS Co-PilotClaudeChatGPTGrokAzure OpenAIIBM WatsonSnowflakeDatabricksData Science

App Modernization

Expert
95%
Legacy → Cloud-NativeMicroservicesKubernetesContainerizationMainframe / COBOL

Integration

Advanced
90%
MuleSoftBoomiJitterbitAPI-Led ArchitectureIBM MQKafka

Pre-Sales & Solutioning

Expert
97%
DiscoverySOW / PricingExecutive PresentationsDeal ClosureBusiness Case Development

Leadership

Expert
93%
Team Building (15+ SEs)C-Suite AdvisoryP&L ManagementMentoring (500+)Change Management
Executive Differentiator

Business Fluency + Technical Depth

Jory operates at the intersection of executive strategy, technical modernization, and practical delivery. He understands how to communicate with business leaders, architects, delivery teams, and clients — translating complex technology challenges into clear business decisions and measurable outcomes.

Can speak business and technology fluently
Understands modernization from discovery to delivery
Strong executive presence and client credibility
Experienced in complex enterprise environments
Outcome-focused, not tool-focused
Comfortable leading through ambiguity
Brings both strategy and execution discipline
Personal Foundation

Built Through Resilience. Focused on Impact.

Behind the executive profile is a story of resilience, accountability, and relentless growth. Jory's leadership is shaped by real life, hard-earned perspective, and a deep belief that transformation is personal before it becomes organizational.

That perspective shows up in how he leads teams, builds trust, navigates pressure, and helps organizations move forward when the path is complex.

"The best leaders are not built in comfort. They are built through pressure, purpose, and the decision to keep moving forward."
For Recruiters

Is Jory the Right Fit for Your Role?

Everything a recruiter or hiring manager needs to quickly assess alignment — role targets, ideal company profile, compensation expectations, and cultural fit signals.

Target Roles

  • Senior Director / VP of AI Transformation
  • VP of AI Solutions & Strategy
  • Head of AI Shared Services / AI Practice
  • VP of Application Modernization
  • Director of Enterprise Architecture
  • VP of Pre-Sales / Solutions Engineering
  • Associate Partner / Technology Consulting Leader
  • VP of Client Technology Strategy

Strong Match If Your Role…

  • Requires executive stakeholder alignment and board-level communication
  • Needs someone who bridges business strategy with technical execution
  • AI strategy, shared services, or practice-building mandate
  • Application modernization, cloud transformation, or AI governance focus
  • Hybrid or remote-friendly leadership culture
  • Values outcome-oriented delivery, not just process compliance
  • Collaborative decision-making with autonomous execution authority

Not the Right Fit If…

  • Pure individual contributor or staff augmentation roles
  • Heavily bureaucratic environments with low tolerance for initiative
  • Roles requiring deep detail work (precise, repetitive, compliance-only)
  • No path to executive authority or expanded responsibility

Location & Logistics

Based in: Dallas / McKinney, TX (DFW)

Work model: Hybrid or remote preferred. Open to travel for client-facing executive roles.

Relocation: Open to discussing for the right VP/Director opportunity.

Authorization: US Citizen — no sponsorship needed.

Ideal Company Profile

  • Enterprise software, cloud services, or technology consulting firm
  • Global IT services company (systems integrator, Big 4 tech, boutique)
  • Technology vendor seeking a client-facing executive leader
  • Enterprise or Fortune 500 internal IT leadership

Awards & Recognition

  • President's Club — 2005, 2007, 2008, 2009, 2014, 2016, 2018
  • SE/SC of the Quarter — 8 times
  • 312% of Quota (2014)
  • Air Force Achievement Medal
  • IBM Extreme Blue Tech Leadership
  • IBM Global Sales School Graduate

Ready to have a conversation?

Reach out directly — Jory responds promptly to serious opportunities.

AI-Powered Tool

Role Fit Matcher

Paste a job description and get an instant AI-powered fit analysis — see how Jory's capabilities align with your role before you reach out.

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Trained & Certified By

Institutions and platforms behind Jory's 40+ certifications

Red Hat
IBM
Google
Harvard
MIT
Oracle
Pega
TEKsystems
AWS
Microsoft
Coursera
Vanderbilt
Thought Leadership

Ideas That Move Enterprises Forward

Why Application Modernization Fails Without Business Alignment

Coming Soon

The Executive Case for Reducing Technical Debt

Coming Soon

AI Is Not a Feature — It Is a Business Model Shift

Coming Soon

Legacy Systems Are Not the Problem. Unclear Strategy Is.

Coming Soon

From Cloud Migration to Business Transformation

Coming Soon

What Modernization Leaders Need From Their Consulting Partners

Coming Soon
Beyond the Executive

One Mind. Many Dimensions.

Strategy and modernization are the headline. The full story is broader — engineer, scientist, artist, musician, writer, and lifelong learner. Curiosity doesn't have a job description.

Published AuthorEnterprise Software ConsultantExecutiveBusinessmanDistinguished Solutions ArchitectThought LeaderSpeakerEntrepreneurDadEngineer — Electronic, Computer, Mechanical, Hydraulic & Fluid DynamicsApplied ScientistQuantum Computing NerdVenture CapitalistCar Guy
Comedy WriterDrummerSketch ArtistPainterSculptorHonor Roll StudentFrequent NapperWord Maker-UpperThin Cheese Slicer
Let's Connect

Ready to Modernize What Matters?

For organizations looking to modernize platforms, align strategy with execution, accelerate delivery, and create measurable business outcomes, Jory brings the leadership, experience, and perspective to help move the work forward.

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