Team & Partners
It started with T-Mobile’s Strategic Journey Towards Innovation and Growth…
In 2018, T-Mobile embarked on an ambitious journey to explore business models and services beyond its core wireless services. Kevin McCaffrey led this work, reporting directly to the Executive Vice President of Strategy. Recognizing the limitations of conventional innovation methodologies, the enterprise sought an outsider to impact not just the strategy and process, but the way they worked.
Forging a New Path with Expert Collaboration
The quest led Kevin to engage with leading thinkers and strategists in the field. His pursuit of excellence drove him to consult several industry experts, delve into influential works such as “The Amazon Way on IoT,” and ultimately collaborate with John Rossman. Throughout two and a half years, John served as the senior innovation advisor to T-Mobile.
Crafting a Playbook for Transformation
Their collaboration was not just about adopting new technologies or practices; it was a deep dive into the very fabric of organizational change and leadership. Through their combined efforts, they developed a playbook focused on the spefics of “high-potential, high-risk” initiatives. These are “big bets”.
The Legacy of Big Bet Leadership
The insights and methodologies born from this collaboration transcend the specific context of T-Mobile. They represent a blueprint for organizations aspiring to innovate, transform, and lead in an ever-evolving business landscape. This experience and strategic wisdom are now encapsulated in Big Bet Leadership, a playbook for the perilous job that senior leaders have in leading transformations.
Their new book, Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper-Digital Era will release on Feb 27, 2024.
Managing Partner, Founder
Industrial Engineering, Oregon State University
John Rossman is a business strategist, operator, and expert on digital transformation, leadership, and business reinvention. He has consulted with many great brands including Novartis, Fidelity Investments, Microsoft, Walmart, and Nordstrom. He served as senior innovation advisor at T-Mobile and senior technology advisor to the Gates Foundation. He is an operator and builder whose love is diving into business problems and customer needs designing solutions and business opportunities.
Former Amazon Executive Responsible for the launching and scaling the merchant integration team and played a key role in launching and scaling the Amazon marketplace business, which is now over 50% of all units sold at Amazon.com. Also responsible for the enterprise services business with responsibilities for Toys R Us, Target.com, NBA.com and other great brands.
Media Analyst Sought after expert commentary regarding Amazon as interviewed by New York Times, CNBC, Yahoo Finance, Bloomberg, BBC, Geekwire and many others.
Author Author of Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper Digital Era. Releases Feb 27, 2024. Author of Think Like Amazon: 50 1/2 Ideas to Become a Digital Leader. Author of The Amazon Way on IoT: 10 Principles for Every Leader from the World’s Leading Internet of Things Strategies. Author of The Amazon Way: Amazon’s 14 Leadership Principles.
Assignments - Interim chief technology officer for the Gates Foundation - Innovation advisor to T-mobile - Interim CIO for a national retailer
Speaker Keynote speaker on innovation, leadership and digital transformation. John leads workshops on a wide variety of innovation, internet of things, digital strategy, and creating a culture of agility, trial and error, scaling and accountability. His goal is to give audiences tools they can immediately use to operate differently.
Advisor Rossman Partners helps it’s clients compete and win in the digital era. I work with my clients to both define strategy and create change for the organization. Bringing a broad range of expertise and trusted partners to the table, I first listen and understand, and then help create a customized approach for your situation.
University of Chicago, MBA
Kevin McCaffrey is an expert in Strategy Operations (StratOps) and focuses on the design of user-centered approaches to optimizing delivery of the most important strategic decisions that leaders must get right.
Kevin is a strategist with a passion for operations. He designs, and implements world-class approaches for defining trajectory-shaping strategies into reality. He empowers leaders to manage the success of their organizations through high quality, fast decision making in the fields of Big Bets, resource allocation, and metrics-driven operational interventions.
Author Author of Big Bet Leadership: Your Transformation Playbook for Winning in the Hyper Digital Era. Releases Feb 27, 2024. Co-author with John Rossman
Director, Strategy and Operations for Google Ads Established the Operations team within Google Ads, growing the team from 1 FTE to 12 FTEs within the first 6 months. Our team supported the operationalization of Google Ads' long-term strategy while supporting near-term business steering of the $250B+ business. We accomplished this by (1) supporting executive-level resource allocation decsisions, (2) establishing a comprehensive metrics ecosystem, and (3) running core executive decision processes and forums.World" by Intercon, the Internet Tech conference - Member Newsweek Expert Forum, a community for pioneering thinkers and industry leaders
T-Mobile, Growth Agenda Management.
McKinsey Consulting Engagement Manager
Finance, DePaul University
Manny Bernabe helps companies compete in a data-driven world. He is an expert in AI, machine learning, analytics, and data management technologies. Manny assists clients with AI strategy formation, use case identification, AI pilot management, and employee training.
Most recently, Manny was the Head of AI Product and Lead Data Scientist at Uptake, an AI industrial IoT startup that was listed as #3 on Forbes Most Promising AI Companies in America in 2019.
Prior to Uptake, Manny held the role of Investment Strategist for FlexShares. line of Northern Trust Asset Management. At FlexShares, Manny designed and launched quantitative financial products totaling +$13 billion in assets under management.
Manny earned his B.S. in Finance (Honors) from DePaul University, a Data Science. Specialization from Johns Hopkins University, and has passed all three levels of the Chartered Financial Analyst (CFA) exam series.
Digital and Innovation Advisor
Bainbridge Island, Washington
Mr. Arens was a Managing Director at Alvarez & Marsal. Prior to that, he was Vice President of Merchant Services and Sales with Amazon where he was in charge of the commercialization of Amazon’s overall enterprise services business and responsible for driving enterprise direct sales, channels, alliances, and partnerships.
Former Amazon Executive Vice President of Merchant Services and Sales with Amazon where he was in charge of the commercialization of Amazon’s overall enterprise services business and responsible for driving enterprise direct sales, channels, alliances, and partnerships.
Background Mr. Arens was a Managing Director at managing consulting firm Alvarez & Marsal. Prior to that he was Vice President of Merchant Services and Sales with Amazon where he was in charge of the commercialization of Amazon’s overall enterprise services business and responsible for driving enterprise direct sales, channels, alliances, and partnerships. Mr. Arens was a senior executive at Syncra Systems, a supply chain management company providing B2B internet-based collaborative planning, forecasting, and replenishment solutions. Mr. Arens started his career at IBM and served in various senior level sales management roles during IBM’s historic transformation from a hardware company to a services company. When he left he was responsible for IBM’s overall global B2B market place initiatives.
Consultant to CEOs Mr. Arens’ specialty is creating pragmatic digital strategies based on Amazon’s principles of leadership and customer innovation. Wes collaborates closely with CEO’s to refine their own vision for digital, define their unique market point of view for superior customer value, and build a roadmap to improve business outcomes. He knows the hard questions necessary to challenge and transform the business and can objectively assess internal capabilities and gaps and illuminate blind spots including talent acquisition. In the end Mr. Arens helps organizations build a plan to accelerate the speed and quality of day to day decision making. His approach has helped dozens of companies unlock their own brand of innovation and prioritize the bets necessary to transform and improve results.
Speaker Frequent keynote speaker and leads workshops on a wide variety of innovation, internet of things, digital strategy and creating a culture of agility, trail and error, scaling and accountability. My goal is to give people tools they can immediately use to operate differently (like we would at Amazon). Please contact me to discuss your event (email@example.com)
- Digital Transformation Strategy and Execution
- SaaS Business Positioning, Strategy, and Roadmap
- Senior Innovation Advisor for T-Mobile
- Technology Assessment and Interim CIO
- Gates Foundation Senior Technology Advisor
- AI Natural Language Processing Solution Development
- Technology Due Diligence for PE Investor
- Customer-Centricity Strategy for Global Pharmacy
- Innovation Masterclass -- Think Big but Bet Small
- Board Advisors to Mid-sized and Startup Leaders
- Executive Team Goals and Objectives Definition
Product & Digital Transformation Strategy and Execution
Engaged by public company CEO to establish a customer and employee experience reinvening the experience through mobile access, reducing friction and eliminating operating costs. This strategy and plan has been the backbone of creating scale for this national staffing organization.
Following the digital vision and strategy, we conducted an technology and IT organization assessment, served as interim CIO, hired and transitioned to new technology leadership team. Improved both operational stability and ability to release new features and improved data quality.
B2B SaaS Product Value Proposition, Strategy and Roadmap
Engaged by multiple SaaS technology companies to develop a compelling product mission and value proposition. Engagements typically end with the development of an investor deck, client presentation and comprehensive roadmap. There are several keys to this type of engagement. Working as “one team” with a small and consistent client team gives speed, the advantage of company expertise, but balanced with an independent point-of-view and fresh mindset.
Interviewing customers, ecosystem players and partners to gain industry and “job-to-be-done” insights is important to bring new insights to the existing strategy. We typically leverage parts of the Amazon “working backwards” approach and write different and alternative versions of future press releases, FAQs, narratives and low fidelity prototypes to stretch the existing thinking. We often leverage “category definition” approaches to frame, name and claim a new category which we can dominate.
Senior Innovation Advisor for T-Mobile
Retained by T-Mobile corporate strategy team as advisor in building a enterprise innovation program. Developed framework, processes and governance for end-to-end innovation program. Developed scanning and strategic themes, conducted due diligence, collaborated on key concept envisioning, established resource management processes.
Resulted in scaling second and third horizon investments in emerging markets and established ongoing innovation program.
Technology Assessment and Interim CIO
We have conducted multiple cloud transition plans, IT and engineering process and organization reviews, and served as interim leadership. Developed API business model strategy and current-state assessment of the power and gap of current offering.
Provide full-cycle software architecture services, including designing, developing, reviewing, tuning, and improving complex software frameworks. Whether you’re working with new software or an outdated legacy system, we can help you optimize it. Our proven methodology has helped clients achieve over 25% faster time-to-market and superior scalability with their applications.
Gates Foundation Senior Technology Advisor
I served as the Senior Technology Advisor to the US Program of the Gates Foundation and led dozens of teams and projects on behalf of the Foundation.
These projects included laying the groundwork for a longitudinal student-data standard and building momentum and an ecosystem for its adoption and use; led the technical architecture and teams in a massive investment from the Gates Foundation into a national marketplace of apps and data to enable teaching innovation through a company named InBloom; assisted several states in successful applications in the Race To The Top federal funding program.
AI Natural Language Processing Solution Development
Envisioned, designed, engineered and launched an API to innovate business email. Conducted market and user research to reinvent business email. Developed data labeling application, designed and coded NLP model and API, developed prototype of UI and user experience.
Resulted in API being acquired by startup as the core engine for innovative CRM application targeting business professionals.
Technology Due Diligence for Private Equity & Investors
Conducted due diligence for PE investment into Amazon ecosystem technology provider. Based on a deep understanding of the Amazon marketplace ecosystem, we were engaged by a large PE firm evaluating a majority investment into a technology company. Due diligence evaluated user satisfaction, technical risks, competitive landscape and identified “unfair advantages” target company represented.
The engagement resulted in a successful investment.
Customer-Centricity Strategy for Global Pharmacy
Building on multiple keynote speeches and workshops with worldwide leadership team, was retained by divisional president to assist in develop a strategic change program on customer centricity. The goal was to breakdown organization structure and bureaucracy to create insights, programs and investments to serve patients and providers through an effortless experience
Resulted in an influence-oriented strategy equipped with principles, toolkits, comprehensive communication plan and center of excellence to infuse customer-centricity overcoming current product-centric mindset
Masterclass on Innovation and IoT — Think Big but Bet Small
Delivered multi-day masterclass training session for senior leadership. The class address leadership, visioning, prototyping, leveraging Amazon’s “working backwards” techniques to help participants begin the development of a rigorous digital plan. Included technology sessions from AWS and industry examples from companies like Decisiv and Modjoul.
This class can be customized for the needs of the participants
Board Advisors to Mid-sized and Startup Leaders
Serve as board-advisors to a variety of mid-sized and startup companies. This includes
- SupplyClinic — A marketplace for trusted dental supplies
- Decisiv — A SaaS platform connecting truck OEMs, dealers & fleet operators to improve the service experience and optimize operating uptime
- Modjoul — An internet-of-things wearable device and data platform transforming blue-collar worker safety
- An Amazon marketplace-first brand incubation platform
- VxtraHealth — A health insurance provider developing and managing health plans without the hassles for self-insured, middle-market employers
Executive Team Goals and Objectives Definition
Engaged to help the executive team define and prioritize their goals, and then to execute better across them. We leveraged the OKR (Objective, Key Results) methodology to quickly define both annual goals and then create quarterly plans and “key results” tied to these. This approach helped the executive team come to better understand the assumptions, risks and dependencies to their plans, to say “no” to non-prioritized distractions, and communicate across the organization in a consistent manner. Allowed the executive team to collaborate more effectively, ask better questions and debate trade-offs while keeping accountability clear.
Achieving growth has been a key focus in these assignments and the early value we delivered was by helping to define strategic growth versus growth which did not provide enhanced value. These assignments often have an executive coaching element in helping individuals with aspects they may be new to or are struggling with. We conducted OKR training and often implemented an “executive” book club as part of these engagements to create the lasting changes required.