Jim Kaskade Resume (multidisciplinary) 091925.pdf

A results-driven, multidisciplinary business leader with over 30 years of executive experience, specializing in enterprise SaaS applications, AI-powered solutions, security, and sophisticated machine learning / deep learning analytics. Over the past 9 years, led two PE-backed companies: recently Conversica, category leader in AI automation for revenue teams, and Janrain (acquired by Akamai), category leader in consumer identity and access management. Prior to that, spent 2 years as an executive at DXC Technology (formerly CSC), managing a billion-dollar P&L and leading large-scale digital transformation initiatives for Fortune 500 enterprises.


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

1. JIM KASKADE
LinkedIn Profile

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


CHIEF EXECUTIVE OFFICER
A results-driven, multidisciplinary business leader with over 30 years of executive experience, specializing in enterprise SaaS
applications, AI-powered solutions, security, and sophisticated machine learning / deep learning analytics. Over the past 9 years,
led two PE-backed companies: recently Conversica, category leader in AI automation for revenue teams, and Janrain (acquired by
Akamai), category leader in consumer identity and access management. Prior to that, spent 2 years as an executive at DXC Technology
(formerly CSC), managing a billion-dollar P&L and leading large-scale digital transformation initiatives for Fortune 500 enterprises.


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 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 $1 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: EIR at Palo Alto Research Center (PARC) - Recruited Yahoo! Cloud CTO and led 10 PARC researchers resulting in
spinning technology out into Quantiply (AI for AML); EIR at Express Ventures - spun technology & team out of UCSD
Supercomputing Center to create StackIQ (Private Cloud Management).

2. PROFESSIONAL EXPERIENCE

Conversica Inc., San Mateo, CA October 2019 to June 2025
The 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.

● Grew from unknown, 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 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% mid-market & enterprise ARR growth, respectively.
Janrain Inc., Portland, OR April 2016 to January 2019
The 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 (previously Computer Sciences Corporation), Falls Church, VA 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.

● 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.

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 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 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, established strategy to target “white-space” through an outsourced data analytics model, and
ramped Fortune 2K sales with a methodical marketing and sales strategy.

PARC, Palo Alto, CA 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).

SIOS Technology, San Mateo, CA January 2010 to June 2011
SVP & GM at an open source software, IT analytics, global Cloud, and disaster recovery solutions company.

StackIQ / Express Ventures, San Diego, CA January 2009 to December 2009
Chairman & CEO at a developer of at-scale on-premise clusters and private Cloud Computing management solutions / Incubated as EIR @ Express.

Eyespot Video Network, San Diego, CA March 2005 to December 2008
Chairman & CEO at digital media SaaS providing broadband & mobile video publishing, syndication, and advertising.

INCEP Technologies, San Diego, CA November 1999 – December 2004
CEO at a developer of first-of-its kind ceramic and organic ball-grid array package for CPUs, GPUs, and ASICs.


EDUCATION

Master of Business Administration in New Product Development, Marketing, and Finance ∙ University of San Diego
BS Electrical Engineering & Computer Science in Distributed Systems, Semiconductor Design ∙ UC Santa Barbara