Chameleon Collective

•  Assessed on-prem, legacy ERP solution evaluating scalability, cost, and long-term viability.
•  Recommended modernization options, including upgrade, replacement and cloud migration.
•  Created comprehensive Product Requirements Document (PRD) capturing business requirements.
•  Produced architectural diagrams of current system to identify gaps, risks, and opportunities.
•  Partnered with business leaders to align technology roadmap with operational and strategic goals.

Fractional CTO - Durvet

A leading D2C collector platform, focusing on numismatics, high-end collectibles and gold and silver bullion.

• Built a Product Development group, laying out a product roadmap for 2025.
• Managed Technology Group.
• Lead initiatives for implementation of new CCaaS, CDP, Salesforce Sales, Service & Marketing Cloud, rebrand/rebuild of ecommerce site (Govmint.com) and cloud migration from 2 data centers. 
• Spearheaded major value-add and cost-savings in solution licensing, managed services and offshoring.

Interim CPO | CTO- Asset Marketing Services, LLC

An NYC-based digital agency that builds businesses and brands online.

• Lead efforts to create and document, compliance & security procedures.
• Recommend security measures (i.e. managed services, phishing test, PEN testing, etc.).
• Serve as mentor and sounding board to current technology leader.

Fractional CISO | CTO - Digital Pulp

HushConcerts provides innovative silent disco equipment solutions and production for events of all kinds, nationwide.

• Provide a sounding board for CEO in various matters associated with running the company.
• Assist in evaluating current technology and processes.
• Help to define strategies to improve customer conversion and retention.
• Strategize around rationalizing / streamlining processes, hardware and software.
• Assist in reviewing cross-functional dependencies and functions.

Advisor & Mentor to CEO - HUSHConcerts

Our Collective solves challenges across business, brand, product, executive recruiting and technology. We've developed a flat, flexible, efficient model that allows us to support our clients by providing leadership that drives change and accelerates growth, subject matter experts that can execute challenging tasks, and the ability to find and help build top-tier in-house teams through our network.

We believe our approach is the future of work. We've reinvented the traditional company by removing traditional hierarchies, unnecessary costs, and inflexibility. Our approach attracts multi-disciplinary leaders and entrepreneurial free thinkers that self-manage and solve meaningful challenges for our clients. The approach that sparked our company will revolutionize yours.

I specialize in technology consultation and interim leadership in:

•  Startups, PE/VC Advisory and Interim Leadership (CDO | CIO | CTO)
•  Datacenter & Cloud Ops Streamlining
•  Digital Transformation & Innovation
•  Technology Operations
•  Cloud Services (IaaS, PaaS, SaaS)
•  Compliance & Security
•  eCommerce (DTC/B2C)
•  KPIs & Analytics
•  Vendor Selection
•  Product / Project Management

Chameleon Collective, Partner - Fractional / Interim CDO | CIO | CTO

The leading provider of higher education enrollment, student success, and fundraising solutions.

• Reported directly to CEO & BOD.
• Managed all aspects of technology; product engineering, infrastructure, data sciences, data operations, support, call centers, security & compliance.
• Developed technology future-state vision & strategic plans w/concentration on innovation.
• Provided in-depth organizational & staffing reviews - executed reorg, hired key roles.
• Managed 100% remote FTEs, onshore & offshore managed services company & vendor management.
• Initiated & managed key projects; marketing automation, ETL solution, data insights, AI implementation, migration to cloud.
• Conducted comprehensive cloud & data center assessments, vendors & solutions & executed streamlining saving hundreds-of-thousands of dollars.
• Worked with key stakeholders to identify top priority issues limiting the businesses ability to renew existing client & move the needle to promote features, functionality & solutions for new client signings.

Interim CTO | CISO - Ruffalo Noel Levitz

Wealthflix is a streaming service where you can watch informational financial courses focused on trading crypto and real estate from celebrities and leaders in the industry.

ADA Consultant - Wealthflix

Joshua Tree National Park Association

Joshua Tree National Park Association is a nonprofit organization management company, supporting the Joshua Tree National Park.

Board Member

Kronos Fusion Energy

Kronus Fusion Energy's mission is to seamlessly intertwine cutting-edge technology with a deep-rooted appreciation for nature, paving the way for a cleaner, more sustainable future. We focus on the development and commercialization of advanced fusion energy technologies, honoring the environment and fostering global peace and long-term economic stability.

Board Advisor & Chief Technology Officer

Greenwood Consulting LLC

Advisor to C-level, business executives, PE and VC firms on strategic technology transformation initiatives. Clients include highly regulated compliance industries (i.e.: Banking, Healthcare, Higher-Ed, FinTech and Insurance), ecommerce, entertainment, retail, logistics and supply, and manufacturing.

•  Orchestrate development of IT vision and strategic plans w/concentration on innovation
•  Provide in-depth organizational and staffing reviews
•  Nearshore & Offshore software development, cloud services & QA
•  Telco assessment, CCaaS recommendations & cost-reduction. 
•  Conduct comprehensive Cloud and Data Center assessments - IaaS / PaaS / SaaS
•  Keynote presenter at major global conferences to CEOs, CIOs and IT professionals

Executive Advisor & Consultant

MGA Entertainment

MGA Entertainment is a global consumer entertainment products company, and the world’s largest privately-held toy company, with over $2.2B+ in annual revenue, MGA has a diversified portfolio of award- winning brands in addition to TV series, feature films, games and music soundtracks.

Reporting directly to the Founder & CEO, responsible for all aspects of the company’s technology, including software development, data science, infrastructure, digital marketing, content production, and driving the firm’s digital initiatives through transformative technology solutions.

• Performed global assessment, set transformation strategy, built digital solutions team, and roadmap for cloud computing platforms.

• Created data science function, driving data collection globally; implemented enterprise-level cloud data warehouse, developed sleeping giant inventory solution highlighting >$70M in lost sales annually, and profit in buying tool monitoring cost thresholds increasing profitability for product design >25%.

• Led implementation of SaaS DAM facilitating automation, security, reduction of duplicative content, AI-based metadata creation, digital publication to partners, one source of the truth and jettisoning 8 repositories, saving >$500k annually.

• Implemented SaaS transportation visibility platform improving supply chain and logistics operations, OTIF delivery and improved inventory management, tracking >90% of shipments over ocean, rail and truck.

• Led D2C P&L from -$950k business to multimillion dollar profits, increasing AOV and ROAS, implementing SEO, driving social, and implementing international sales and loyalty program.

• Implemented AI-based ADA compliance solution for D2C and 49 brand sites, curbing ADA suits, saving >$250k annually. 

• Implementing Salesforce CRM and marketing solutions for EMEA with est. 13.5x ROI or >$25M over 5 years.

• Headed efforts to ‘walk the digital aisles’ (B2B) on Amazon, Target and Walmart, generating >$50M in sales annually.

EVP, Chief Digital Information Officer

Paul Hastings

With 22 offices and $1.8B+ of revenue. Paul Hastings serves a diverse client base including many of the top financial institutions and Fortune 500 companies.

Reporting to the CAO, responsible for global technology, driving digital initiatives and continuous improvement through transformative technology solutions, products and processes, aligning with broader global functions and lines of business. Worked with cross-functional groups to deliver a technology strategy and vision. 

• Drive continuous improvement and delivery of initiatives including transformation to an agile SDLC, processes and tools and change control mechanisms tied directly to client compliance and regulations.

• Lead the Digital Solutions Board, representing technology on product councils, client compliance and risk committees. Strategize and implemented data privacy and cybersecurity measures using data protection by design. 

• Designed and developed matter management and client-facing dashboard solutions on the Salesforce platform – a first for an Am Law 100 firm - providing a transformative digital platform with a focus on automation, analytics, mobility, reliability, security and scalability. Increased user engagement from 60 users to 1k+.

• Developed an award-winning tool to collate and analyze historic LevFin deal data in order to provide clients with comparative market information ahead of a deal.

• Orchestrated a rebuild of the firm’s website, from UEX to integrated data feeds and a headless CMS, moving from on-prem to AWS, resulting in savings in excess of $450k annually and a 99.9% uptime. 

• Working with InfoSec and the OGC, created search solution architecture for CCPA, GDPR, and PII. Developed data warehouse, orchestrating data-mapping activities in preparation for governance models.

• Delivered a cloud-based pitch and proposal solution to aggregate relevant experience, allowing the firm to compete for new and expanded business opportunities with current and potential clients.

Chief Digital & Innovation Officer

Hyperloop Transportation Technologies, Inc.

An innovative transportation and technology company focused on realizing the Hyperloop, leveraging technology, crowd collaboration and a passionate community of global experts to bring disruptive innovation to the transportation industry. 

• Responsible for digital initiatives including orchestration and development of IT vision and strategic plans and product roadmaps.

• Managed teams of technologists and QA engineers working remotely and globally.

• Supervised technology implementation through recommendation, deployment, and effectiveness assessment.

• Architect application UEX and data pipelines for web/mobile applications.

Chief Digital Officer (CDO)

Live Nation Entertainment

World’s leading live entertainment, and ecommerce company: Ticketmaster.com (TM), Live Nation (LN) Concerts, Artist Nation (AN) and LN Network (LNN). TM is a global ticketing leader, and top 5 ecommerce site, with combined revenue of $22B+, over 26MM monthly unique visitors, and a database of 120MM+ fans. LN produces 28,000 events annually for more than 2,300 artists. AN is the world’s top artist management company, representing 200+ artists. These businesses enable 800 advertisers to tap into 250 million consumers annually through LNN’s digital platforms. LN signed superstars Jay Z, Madonna, Nickelback, Shakira and U2 to 360-deals, managing releases, promotion, merchandising, tours, and sponsorship.

• Reporting directly to the CIO, provide executive leadership for cross-functional, global IT teams. Responsible for Development, Business Analytics, Infrastructure, ERP, Vendor Management, PMO, QA, SCM and build support for LNE and Ticketmaster systems; including artist management sites, and concert event booking apps, MusicToday (fan sites & merchandising), and VIP program sites, HR systems, internal ticketing resolution, enterprise systems, LN Merchandising, House of Blues, POS (F&B & merchandising), and digital signage (OTT) for LNE O&O venues. 

• Developed platform supporting LNE BUs, with combined annual revenue of $195MM+ facilitating rapid deployment of microsites; VIP ticketing sites, NA box office fulfillment, HouseofBlues.com, Global Touring, LNE O&O clubs, theaters, and amphitheater sites, meeting PCI requirements, fully integrated with TM event feeds, and payment systems. Developed on cloud PAAS, resulting in millions of dollars in savings on infrastructure, and staff.

• Support global enterprise apps and tools with 350 offices worldwide, and over 14,000 employees, e.g. Appetize, AWS, Azure, Box, Cisco, Confluence, Infra, Jira, Micros, O365, Okta, Slack, Sharepoint, SAP B-1, Successfactors, Yammer, Workday

SVP of Global Technology 

Reporting to the SVP of IT Systems, provided executive leadership for teams consisting of Development, PMO, QA, POS, and SCM for Live Nation and Ticketmaster business systems; including: 
 
•  Directed development, maintenance, and infrastructure for a collection of sites for LNE's O&O Clubs and Theaters, Premium Seat Sales, VIP ticketing sites, HouseofBlues.com, and artist and concert event booking system.  
 
•  Managed internal ticketing resolution systems, and SDLC tools (Atlasssian, Jira, Confluence, Infra). 
 
•  Directed, and maintained Business Enterprise systems (MS Sharepoint, Okta, Box, Salesforce, Successfactors).  
 
•  Responsible for House of Blues systems (labor, kitchen management, catering, scheduling, Crunchtime). 
 
•  Provided business objects (BO), analytics, reporting (event reporting, B2B reporting, settlements). 
 
•  Responsible for development, maintenance, and support of POS, and Digital Signage systems for HOB, venues and amphitheaters (NCR Quest, Appetize, Micros 9700/Simphony, ConcertVision, and Cisco Stadiumvision).

VP of Business Systems

Reporting directly to the CTO, served as a member of the executive management team, participating in forecasting next generation needs, providing QA, SCM and build support for web-based concert promotion and ticketing sites; including Livenation.com, House of Blues (HOB.com) and MusicToday. Responsible for BO reporting, promotional sites and programs, applications, APIs and robust ticketing platform (CTS Eventim). 

•  Built world class QA and Release Management group, overseeing daily operations for team comprised of supervisors and analysts spread across multiple global locations, developing and establishing policies, processes, and systems that fostered smooth workflow, and consistency.

•  Served on team that re-designed core LN web site, resulting in sales of 6.9mm tickets (141% of target) in 2009 and attracted 5mm unique visitors each month. Visits from natural search increased 46% year-over-year and homepage bounce rates decreased by 50% year-over-year. Awarded “Top 5 online music portal” (Nielsen Net View).

•  Played key role in launching in-house ticketing and e-commerce platform. Platform sold 9.8mm tickets total and generated over $500mm in revenue overall in 2009; 2nd largest primary ticketing system for concerts in North America, used by over 300 internal employees and projected to sell over 10mm tickets in 2009.

•  Responsible for developing and maintaining department budget and capital expenditures, while constantly assessing operations to optimize utilization of resources, reduce costs, and enhance quality.

•  Instrumental in Live Nation, Ticketmaster merger activities, vetting, analyzing, and identifying systems, and talent to assist smoothly integrating people, tools, and processes into newly formed Live Nation Entertainment company.

VP of Quality Assurance & Release Management

Temecula International Film & Music Festival

Filmmakers and Musicians from across the globe come to Temecula every September since 1995 to participate and enjoy in the celebration of the two most influential, most enduring, most entertaining art forms, and commerce of film, and music.

A former musician, with an extensive entertainment background, Jon was asked to be the Executive Director of Music for the 18th Temecula International Film & Music Festival. Prior years the festival featured a single night, and a handful of local talent. Jon vetted thousands of international bands to 12. Bands traveled from as far away as Canada, Michigan, and Paris, France. Additionally, he designated children’s bands for openers, including Fender Guitar Center’s Kids-Rock-Free Band, and David Reuther’s (2013 Grammy Nominee) Kids Vocal Studio Band, and split the music festival into two nights. Jon put together 2 headliners, including Randy Scott, Guitar Center’s King of the Blues winner, and an all-star band, members of; Pink Floyd, Steve Miller Band, Rod Stewart, Van Morrison, Keb Mo, and Elton John. Jon called upon Alan Parsons (The Beatles, Pink Floyd, Alan Parson’s Project) to perform, and charged admission for the first time. Lifetime Achievement Awards were given to Alan Parsons, and Arturo Sandoval. 

Jon produced the festival, created the art for posters, opened his home to board musicians, and provide a place for the all-star band to rehearse, and raised funds of over $10,000 to supplement festival activities. 

The festival has typical attendance of between 15-18 thousand, is a non-profit, and partnered with Deaf West Theater (where a portion of the proceeds go), an organization who’s mission is to directly improve and enrich the cultural lives of the 1.2 million deaf and hard-of-hearing individuals who live in the Los Angeles area, providing exposure and access to professional theater, facilitating production of subtitled films for the deaf. Deaf West Theater is a 501(c)(3) non profit organization.

Executive Director

Sony Corporation of America

With over 160,000 employees worldwide Sony is a leading manufacturer of audio, video, communications, entertainment, and IT products for the consumer and professional markets.

Reporting to the GM, developed and maintained promotional efforts and release management of ecosystem for music, mobile, eBooks and video content, while acting as liaison between cross-functional divisions and content providers - integrating efforts of SCA, SEL, SOE and PlayStation divisions. Built group’s first QA and UEX department.

• Oversaw developers and ops staff. Responsible for content VOD/OTT, publisher relationships, contracts and operations; content reception, encoding, cleaning and formatting of content / metadata, packaging w/DRM and publishing.  
• Developed robust content-ops to capture and preserve mobile, music, eBook and video content assets across multiple formats and territories. Procured, cleaned and packaged 7M+ music tracks for US and Canada, 20k eBooks, 12k+ videos for PlayStation, and 25 streaming radio stations for SPRINT mobile initiative. 
• Developed a process and workflow for video and metadata, and created requirements and encoding specifications for PlayStation, to deliver content to PSP, PS3 and PC.
• Directed production and usability for promotional production in support of business development and marketing, directing campaign management, editorial and execution for 3rd party promotions; Albertsons, Best Buy, Coca-Cola, Coors, Ford, Intel, Kellogg’s, Reebok, McDonalds and Subway. 
• Produced exclusive, real-time downloads of broadcast performances; e.g. ABC's Jimmy Kimmel, and MTV's Katrina AID.
• Configured and validated data feeds and reports for label aggregators, ASCAP, BMI and CMRRA for appropriate royalty payouts, as applicable for downloads, live performance sales and radio.

Sr. Director of Content Operations & Promotions

Winner: Los Angeles Business Journal’s Enterprise CIO of the Year Award (500+ Employees)

An award-winning technology executive with 20+ years’ experience in IT, product and development of web, mobile and software applications. A prolific inventor, consistently generating new ideas and processes. Especially adept at analyzing and addressing problems that arise during new product design and development and in creating new time and money conserving processes. A dependable, thorough, and well-organized planner, who thrives in an environment that fully utilizes technical and creative skills. 

I've worked on a vast expanse of products and titles in consumer electronics, entertainment, graphics, gaming, legal, retail, manufacturing and office products with companies, and individuals such as: 7th Level, Alan Parsons, Bandai, Bob Ezrin, Disney, Gateway, House of Blues, Howie Mandel, Hyperloop Transportation Technologies. IBM, Intel, Live Nation Entertainment, MGA Entertainment, Micrografx, Monty Python, MusicToday, Paul Hastings LLP, Pink Floyd, Quincy Jones, Sony, Ticketmaster and Warner Bros. 

Specialties: digital transformation, innovation, data analytics, solution and service development, data privacy and compliance, cloud-computing, content operations, call/contact center, infrastructure, project/product management of software and hardware products, SDLC, UEX, human factors, IP generation and team creation.

• Business Development
• eCommerce / Retail
• CCaaS
• Compliance
• Content Operations
• CRM / ERP / PLM
• Digital Transformation
• IaaS / PaaS / SaaS
• IP
• Legal
• PPM
• Project Management / Producer
• Process Improvement
• R&D
• QA
• SDLC
• System Integration
• Team Building 
• UEX

Most companies rushed to use Gen AI in 2024–2025. Far fewer learned how to experiment with it systematically. The real unlock isn’t another pilot or proof of concept - it’s building an organizational experimentation muscle. 

Gen AI value comes less from the model of the week and more from how rigorously your organization learns.

► Treating Gen AI like a general-purpose technology with a productivity J-curve initial dip before durable gains.
 
► Designing disciplined experiments around real customer and operator pain points, not just “cool demos.” 

► Partnering across business, ops, data, and academia to test, refine, and scale what actually works. 

Do you have a clear experiment portfolio for Gen AI tied to specific business KPIs, or just a collection of disconnected pilots? Who actually owns the experimentation agenda in your org today - IT, data, product, ops, no one?

#ai #agenticai #digital #digitaltransformation #experimentation #generativeai #hbr #innovation #technology

Jon Michel Greenwood

Fractional / Interim CDO | CIO | CPO | CTO - Driving Digital Transformation & Innovation through Leadership & Technology Assessments

Open article: A Systematic Approach to Experimenting with Gen AI by hbr.org

A Systematic Approach to Experimenting with Gen AI

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