Jim Kaskade Resume (Artificial Intelligence) 091925.pdf

Visionary technology executive with 30+ years of experience leading AI-native and AI-transformed organizations across enterprise SaaS, data infrastructure, and security. Proven record of turning emerging AI technologies into category-defining products and scaling businesses through GenAI innovation, operational discipline, and GTM excellence. Known for aligning deep technical fluency with business strategy to drive transformative growth and trusted AI adoption across industries. Recent focus includes building and scaling enterprise-grade Generative AI platforms, leading GTM transformations for AI products, and advising startups at the frontier of AI in fintech, regtech, and healthcare.


LEADERSHIP OPERATING MODEL
Culture | Build culturally vibrant teams through radical transparency, fostering trust and high performance
Strategy | Establish clear, customer-obsessed strategies rooted in value creation, competitive advantage, and GTM alignment
Execution | Drive accountability through data discipline, operational rigor, and relentless focus on outcomes


AREAS OF EXPERTISE
Multidisciplinary Leadership | Spanning product, engineering, GTM, finance, and operations
PE-Backed Scaling & M&A | Profitable Growth, Enterprise Value Creation, and Exits
Technology-Enabled Competitive Advantage | AI Agents, CIAM Security, Big Data and Analytics, SaaS
Customer-Centric Strategy | GTM, Revenue Growth, and Market Positioning
Data-Driven Execution | P&L Management, Operational Excellence, and Profitability


SELECTED RESPONSIBILITY PROFILES
DXC Digital Applications | $1B | 12% YoY
DXC Big Data & Analytics | $250M | 51% YoY
Infochimps | $50M | 36x YoY
Conversica | $30M | 30% YoY
Janrain | $22M | 48% YoY

1. JIM KASKADE
LinkedIn Profile

San Francisco, CA 94114 ∙ [phone] Mobile ∙ [email protected] ∙ www.jameskaskade.com


CHIEF AI OFFICER | TRANSFORMATIONAL ENTERPRISE AI LEADERSHIP
Visionary technology executive with 30+ years of experience leading AI-native and AI-transformed organizations across enterprise
SaaS, data infrastructure, and security. Proven record of turning emerging AI technologies into category-defining products and scaling
businesses through GenAI innovation, operational discipline, and GTM excellence. Known for aligning deep technical fluency with
business strategy to drive transformative growth and trusted AI adoption across industries. Recent focus includes building and scaling
enterprise-grade Generative AI platforms, leading GTM transformations for AI products, and advising startups at the frontier of AI in
fintech, regtech, and healthcare.


LEADERSHIP OPERATING MODEL
Culture | Build culturally vibrant teams through radical transparency, fostering trust and high performance
Strategy | Establish clear, customer-obsessed strategies rooted in value creation, competitive advantage, and GTM alignment
Execution | Drive accountability through data discipline, operational rigor, and relentless focus on outcomes


AREAS OF EXPERTISE
Multidisciplinary Leadership | Spanning product, engineering, GTM, finance, and operations
PE-Backed Scaling & M&A | Profitable Growth, Enterprise Value Creation, and Exits
Technology-Enabled Competitive Advantage | AI Agents, CIAM Security, Big Data and Analytics, SaaS
Customer-Centric Strategy | GTM, Revenue Growth, and Market Positioning
Data-Driven Execution | P&L Management, Operational Excellence, and Profitability


SELECTED RESPONSIBILITY PROFILES
DXC Digital Applications | $1B | 12% YoY
DXC Big Data & Analytics | $250M | 51% YoY
Infochimps | $50M | 36x YoY
Conversica | $30M | 30% YoY
Janrain | $22M | 48% YoY


SELECTED AI IMPACT HIGHLIGHTS
● Enterprise Value: Achieved exit value of 7.5x ARR, 3x in Cash on Cash return and 44% in IRR outcome at Janrain; created $2B
additional market capitalization within the largest business unit at DXC/CSC; and achieved 79% IRR with 21x revenue exit at
Infochimps.
● Growth: 40% YoY enterprise and 20% YoY mid-market growth at Conversica ($29M); $5.4M to $17.5M (48% YoY) in mid-
market/enterprise revenue at Janrain in 2.5 years; $0 to $50M in revenue at Infochimps in 2.5 years; drove the highest growth
of business with 51% of YoY revenue growth, from $165M to $250M at DXC/CSC; and delivered revenue growth from -5% to
12% on $1B in six months while exceeding the targeted operating income by nearly 200% (20% OI).
● Sales: From 15% to 80-90% sales productivity at Conversica (4Q24-1Q25), Annual Contract Values (ACV) from $24K (SMB) to
$95K (mid-market) - $180K (enterprise); Grew Janrain enterprise sales win-rates from 4% to 54%, ACV from $18K to $250K,
Total Contract Value (TCV) from $40K to $550K.
● Customer Success: From 67% gross retention / 74% net dollar retention (EoY 2019) to 95% gross retention / 102% net dollar
retention (mid-market & enterprise EoY 2024) at Conversica; GRR from 76% to 90% DRR from 88% to 117% at Janrain.
● Profitability: Burning $1M/mth & EBITDA -18% to 2M FCF-positive and +10% EBITDA at Conversica; Burning 650K/mth to free
cash flow +228K/mth at Janrain; Integrated seven diverse lines of business into a single $1B business unit and improved the
operational profitability from 0% to 20% by managing P&L customer-by-customer.
● Innovation: Forrester Wave Leader @Conversica for Conversation Automation Solutions for B2B. Forrester Wave Leader
@Janrain for Customer Identity And Access Management. IDC declares the “New CSC” after Digital Applications business
turnaround. EIR at Palo Alto Research Center (PARC) - Recruited Yahoo! Cloud CTO and led 10 PARC researchers resulting in
spinning technology out, founding Quantiply (AI for AML); EIR at Express Ventures - spun technology & team out of UCSD
Supercomputing Center to create StackIQ (Private Cloud Management For Large Analytic Clusters).

2. PROFESSIONAL AI EXPERIENCE

Conversica Inc., San Mateo, CA AI Agents for Revenue October 2019 to June 2025
Transformed into category leader in AI-powered Revenue Digital Agents with $29M in annual recurring revenue, serving sales, marketing, &
customer success.

Chairman & Chief Executive Officer
Led business transformation of a PE-backed AI Automation SaaS provider.

● Repositioned from SMB-centric AI vendor focused on automotive to enterprise-centric category leader (Forrester Wave #1) with diverse
industries (FinServe, Technology, Telecom, Manufacturing, Business Services, Entertainment, Education, Health & Wellness) & F500 customers.
● Transformed GTM model: from SMB inside sales (24K ACV) to field-based MM/ENT sales (95K/180K ACV),
● Resulting in turnaround from -$12M to FCF-positive; with 20% & 40% YoY mid-market & enterprise ARR growth, respectively.
Janrain Inc., Portland, OR AI in CIAM / Security April 2016 to January 2019
Transformed into category leader in customer identity & access management SaaS with total annual recurring revenue of $22M.

Chairman & Chief Executive Officer
Led turnaround and M&A process of a PE-backed digital identity security SaaS provider, resulting in 7.5x revenue exit, >3x cash-on-cash & 44% IRR.

● Grew enterprise revenue with clients >$1B from $5.4M to $17.5M (48% YoY) establishing Janrain as enterprise-centric category leader (Forrester
Wave #1).
● Repositioned GTM from marketing to security-first, improving burn from -$650K to +$228K/month; reducing CAC from $6.32 to $1.10 (t3m);
and boosting LTV:CAC from 1.46 to 6.86.
DXC, Falls Church, VA AI Business Transformation August 2013 to January 2016
One of the largest IT service providers Globally, offering technology-enabled software and programming services.

Vice President and General Manager – Digital Applications, Americas BU
Led $1B revenue P&L and a 7,000-person business unit with a focus on Digital Transformation. Created $2B in marketcap value.

● Established a strategic business unit for managing new digital application modernization solutions for Fortune-500 enterprises, including $200M
in consulting and $800M in application development and management. 0 to 20% OI ($200M); -5% to 12% YoY growth ($1B).

Vice President & General Manager - Big Data & Analytics, IoT BU
Led $250M revenue P&L and 1,000-person business unit delivering Data Infrastructure, Business Intelligence, and AI/ML/DL Advanced Analytics.

● Enhanced the organizational structure for growing a business unit (51% YoY) through effective go to market strategy and business
transformation and invested $30M+ in developing “analytics-as-a-Service” solutions.
● Led the integration of Infochimps into a business unit driving 20%+ revenue ($50M) and 33%+ pipeline; redefined sales go-to-market, and
improved traditional offerings (25% YoY) and next-gen offerings (300% YoY).

Infochimps, Austin, TX AI PaaS August 2012 to August 2013
Led an emerging Big Data Cloud SaaS targeting Enterprise 2K with analytics-as-a-Service offering, building from $0 to $50M.

Chairman & Chief Executive Officer
Accountable for leading “playbook” turnaround, growth, and an M&A process, resulting in 21x revenue exit, >3x cash on cash and 79% IRR.

● Developed a first-of-its-kind Big Data Cloud / AI Platform as a Service, established strategy to target “white-space” through an outsourced data
analytics model, and ramped Fortune 2K sales from $0 to $50M with a methodical marketing and sales strategy.

Quantiply / PARC, Palo Alto, CA AI for KYC & AML October 2011 to August 2012
Executive in Residence at a pioneer in the commercialization of advanced AI and human-machine collaboration, digital workplace, IoT and Machine
Intelligence, Digital Design, Microsystems, and Smart Devices. Resulted in Quantiply spinout (Explainable & Auditable AI for AML).

PRE-CEO CAREER IN AI / ML / DL
• Product Management / Product Marketing: In-Database ML/DL (Teraminer), NCR
• Product Management: Data Mining & BI Product Management (KDW / Clementine / SPSS / SAS), NCR
• Technical Consultant: BI Analytics & Database Professional Services, NCR
• Engineer: ML/DL Engineering, NCR

BOARD & ADVISORY POSITIONS IN AI / ML / DL
• GoSeniors (Founder): AI Agent that helps seniors live fuller, safer, and more independent lives—every single day
• SnippetSentry (Advisor): Mobile communications compliance & governance platform
• Quantiply (Board Member): Fighting financial crime by delivering a suite of fully automated artificial intelligence (AI) powered risk and
compliance software that addresses KYC and AML
• Acceptto (Board Member): AI/ML-driven cybersecurity, challenging the norms of identity access with continuous behavioral
authentication.


EDUCATION: MBA ∙ University of San Diego; BS EECS ∙ UC Santa Barbara