Jim Kaskade CV Resume multidisciplinary business leader 082825
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A results-driven business leader with over 30 years of executive experience, specializing in enterprise applications, AI-powered solutions, and SaaS/cloud computing. Over the past 9 years, led two PE-backed companies—Janrain (acquired by Akamai) and Conversica—resulting in category leadership and profitable growth. Prior to that, spent 2 years as an executive at DXC Technology (formerly CSC), managing billion-dollar P&Ls, leading large-scale digital transformation and advanced analytics initiatives for Fortune 500 enterprises.
Jim Kaskade CV Resume multidisciplinary business leader 082825
- 1. JIM KASKADE LinkedIn Profile San Francisco, CA 94114 ∙ (619) 985-6271 Mobile ∙ jim.kaskade@gmail.com ∙ 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: Janrain (acquired by Akamai), category leader in consumer identity and access management, and Conversica, category leader in AI automation for revenue teams. 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 IMPACT HIGHLIGHTS ● Enterprise Value: Achieved 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: 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