Southwest Florida business Leaders Community

Pioneers and Legends, is a business leader community based in Naples, Florida that brings together current and past CEO(s), CXO(s), Board Directors, Founders, Investors, and Advisors, who live in Southwest Florida, and are interested in technology, innovation and leadership. The objective is to connect people, and share insights, inspiration, experiences and expertise, through prominent guest speakers and roundtable discussion.

OUR Mission

the power of community

We are a tech community of current and former leaders in Southwest Florida bringing together professionals, enthusiasts, entrepreneurs, and investors interested in technology and innovation. Here's an outline of what this event will entail:

Invitations and Outreach: Outreach consists of invitations to current and former technology and corporate America executives. Executives from companies such as JPMorgan Chase, Oracle, IBM, PTC, EMC, Tivoli, Sybase, ASG, Sun Microsystems, Informatica and Legent will be invited and attending.
Keynote Speakers and Panel Discussions: Invite keynote speakers who are prominent figures in the tech industry to share insights and inspiration. Guest speakers will share their experience and expertise on a wide range of technology and leadership topics.
Startup Showcase: Provide a platform for local startups to showcase their innovations and products. This will involve setting up booths or demo stations where attendees can interact with founders and learn about their venture.
Networking Sessions: A major objective is the networking aspect. Icebreaker activities, and themed discussion groups can help break the ice and foster meaningful interactions.
Workshops and Skill-building Sessions: Offer workshops and skill-building sessions on topics of interest to the tech community.
Community Building Activities: Encourage community building through social activities such as golf, tennis, and fishing. This could include group outings, charity work and collaborative projects aimed at addressing local challenges using technology.

FOUNDERS

Our founders

the power of community

John P. Calamia
Founder

John formed Oak Point Consulting to focus on sales and sales management recruitment. Since then, he has completed hundreds of searches helping companies build sales teams throughout North America. Prior to entering into the executive search field, John Calamia held a number of distinguished sales leadership positions over a span of 20 years. He maintains a residence in Westhampton, New York and Naples, Florida, and is married with two children.

Les Rechan
CO-Founder

Les is a proven global leader with over 40 years of CEO, COO, GM, board and venture capital experience in AI, analytics, cloud and B2B solutions. He has a breadth of transformational experience in large, complex organizations, as well as smaller to mid-size entrepreneurial environments, including Microstrategy, PROS, IBM, Cognos, Solace, Halogen Software, and Siebel Systems. Les has effectively integrated several strategic acquisitions, and prides himself in being a conscious leader, and delivering valued customer, partner, employee and shareowner partnerships.

Randy Seidl
CO-Founder

Randy Seidl is a global technology board director, CEO, CRO, executive recruiter, sales community leader, consultant, advisor, and investor with extensive sales and executive leadership experience. Put simply, Randy helps companies and individuals grow. He is known for his unique ability to scale emerging growth and Fortune 500 technology companies as well as individual’s careers.

our special guest

Special Guest Speaker:

Ginni Rometty

Former Chairman, President, and CEO of

IBM

Date: January 16, 2025

Arthur L. Allen - Our Host
President & Chief Executive Officer, Adaptive Computing Inc.

Arthur Allen is a successful entrepreneur with 40+ years of strategic experience in the software industry. He built and sold his first software company for $18M by the time he was 34 years of age. As the technology industry entered a new period of intensive growth, Arthur Allen launched ASG Software Solutions in 1986. Mr. Allen built ASG into a multinational corporation with more than 90 offices worldwide. As CEO of ASG, he executed 60+ acquisitions over 29 years - growing the company to over $300M in revenue. He has acquired companies across the USA, Europe and Asia ranging in size from $5-150M - including such entities as Mobius, Atempo, CloudFactory, VisionApp, and PS' Soft.

Dr. Sameer Shende
PhD Senior Advisor and Partner

Dr. Sameer Shende serves as a Research Professor and the Director of the Performance Research Laboratory at the University of Oregon and has a joint appointment in the CELS/MCS directorate at the Argonne National Laboratory. Additionally, he plays an active role as a member of the Office of Science's Advanced Scientific Computing Advisory Committee (ASCAC) at the U.S. Department of Energy.
Within the DOE's U.S. Exascale Computing Project, Dr. Shende served as the lead for the Programming Models and Runtime (PMR) area of the Software Development Kit (SDK). This initiative developed the Extreme-Scale Scientific Software Stack (E4S), a first-class entity in the HPC ecosystem, enabling new conversations with users, facilities, vendors, other US agencies, and international partners.
Furthermore, Dr. Shende serves as the President of ParaTools, Inc. and ParaTooIs, SAS, a consulting firm specializing in parallel and distributed computing, performance evaluation, algorithms, and software development.
His research interests span high performance systems, scientific software, and advanced operating systems, resulting in a publication record of over 170 research papers and engagements as a speaker at events worldwide.

John Calamia
President, Oak Point Consulting

John formed Calamia and Associates in 2001, which was his initial introduction to executive search. After five successful years building a recruitment business, he became a Partner in Leadership Group Executive Search. In 2006, John formed Oak Point Consulting to focus on sales and sales management recruitment. Since then, he has completed hundreds of searches helping companies build sales teams throughout North America. During this period, he has built a formative client portfolio of over 100 technology companies.Prior to entering the executive search field, John Calamia held a number of distinguished sales leadership positions over a span of 20 years. His notable achievements include:

Joined Cullinet Software, the first software company ever to be listed on the NYSE, where he managed the New York area sales operation.
Led Sybase's historical growth in financial services for seven years, resulting in their dominance in the field of financial services.
Recruited to be the first sales manager for the startup Vignette, which in 1998 went public in a record-breaking IPO
Ran North American sales in the financial services sector for Tivoli, a major division of IBM.
Held the title of Vice President of Sales for Riversoft which under his sales leadership went public in 2000 on the London Stock Exchange.

John J. Cullinane
Founder, Cullinet Software

Founder of Cullinet Software, Inc., one of the first computer companies formed to specialize in computer software products. In 1982, 1984, and 1985, Mr. Cullinane was named as The Wall Street Transcript's CEO of the year in the computer software products industry. He was inducted into The Babson College Academy of Distinguished Entrepreneurs and was honored in 1985 at the Fifty-Seventh Annual Awards Dinner for The National Conference of Christians and Jews. Most recently he was inducted into INFOMART'S 1987 Information Processing Hall of Fame. Mr. Cullinane is a graduate of Northeastern University and a member of its Board of Trustees and is a recipient of The Northeastern University Outstanding Alumni Award for Business and Industry. He is a member of the board of several business organizations and is Chairman of the Board of Directors of The John F. Kennedy Library Foundation. “The only true lasting satisfaction in life comes from helping others”.

Randy Seidl
Chief Executive Officer
SALES COMMUNITY, Revenue Acceleration, and Top Talent Recruiting

Randy Seidl is a board director, CEO, CRO, executive recruiter, sales community leader, consultant, advisor, and investor with extensive technology sales, channel, and executive leadership experience. Put simply, Randy helps companies and individuals grow. He is known for his unique ability to scale emerging growth and Fortune 500 technology companies as well as individual careers. He has served as Co-Founder, Board Chairman, Board Director, Chief Executive Officer, SVP/General Manager, and other roles. Uniquely, he has worked in start-ups/smaller companies and industry-leading organizations such as Hewlett Packard, Sun Microsystems, StorageTek, and EMC Corporation. He has a record of consistently increasing company value through his strategic leadership, go-to-market expertise, people skills, and his extensive executive relationship network. All of this experience has involved working with and leveraging the channel and channel partners.

Larry Feinsmith
Managing Director and Head, Global Technology Strategy, Innovation & Partnerships

Larry Feinsmith is a senior member of the JPMorgan Chase Global Technology Operating Committee and Global Head of Technology Strategy, Innovation & Partnerships. He and his team drive innovation and enable JPMorgan Chase's technology strategy through close partnership and connectivity across the established and emerging technology ecosystem. The group is responsible for ensuring that JPMC is meaningfully engaged with new technologies across Cloud & Modern Engineering, Data & Analytics, Digital & Fintech, and Cybersecurity and to deliver strategic value and the next generation of technology solutions Larrys team is also responsible for innovation enablement programs such as hackathons and protecting the firm's intellectual property. Lastly, Larry is part of the JPMC Strategic Investment Committee to determine best in class technology investments.
Prior to joining JPMC in 2008, Larry spent twenty-five years as an executive leader in both the Technology and Financial Services industries. Larry was a senior member of Morgan Stanleys Chief Technology Officer Team from 2002-2008. While at Morgan Stanley, his focus on strategy development was in the software sector including core infrastructure, application infrastructure, information management, collaboration & enterprise / corporate applications and SaaS.
Prior to Morgan Stanley, Larry spent thirteen years working in senior management positions for software companies including Sybase, CrossWorIds Software (acquired by IBM) and Vitria Technology. Larry spent the first five years of his career doing database design and application development consulting with many Wall Street firms including J.P. Morgan.

Bill Seibel

Bill is the Founder/CEO of Gumball, an advisory firm that has helped more than 80 CEOs rapidly scale their company. He has been an important mentor to the people that have worked for him and is proud that more than 150 of them have become CEO’s. Bill recently published his best-seller “Press Go! Lessons Earned by a Serial Entrepreneur” to share both the business and life lessons that he’s earned throughout his career.
Bill earned a BS Engineering from Penn State, an MBA from Carnegie-Mellon, and, after graduation, joined Air Products – a F100 company. In his 12 years there, Bill held executive positions in Supply Chain and Information Technology. Longing to have a greater impact on the business, he left to find that opportunity in the world of startups. Seibel has played a role in 14 startups – 5 as Founder/CEO, 5 as CEO and another 4 as an Operating Executive. They include Cambridge Technology Partners (which he will discuss today); ZEFER ($136M revenue in its first 15 months in business—setting the record as the fastest growing professional services firm ever; named Red Herring’s Top Company to Watch and Gartner’s Magic Quadrant Leader); Demantra (Awarded Top Business Turnaround; acquired by Oracle); and Mobiquity (Fastest Growing Company in New England, One of the Top Mobile Firms in the World (Forrester), One of the Five Coolest Tech Vendors on the Planet (Gartner), and Company of the Year; acquired by Hexaware.
Bill has been recognized as Tech Luminary, Technology CEO of the Year, Penn State Outstanding Alumni, Bishop Canevin Ring of Honor, CEO/Founder of New England’s Top Small Business, a finalist for New England’s Entrepreneur of the Year, featured in Forbes - Mobiquity's Founder And CEO Bill Seibel Is Unstoppable, recognized in 2021 by Governor Charlie Baker for his “many entrepreneurial contributions to the Commonwealth.

Jim Routh

Jim Routh is currently on the Boards of Supply Wisdom, Savvy Security, Accountable Digital Identity Association, and the Global Resiliency Federation. He is the former Board Chair for the Health Information Sharing & Analysis Center (H-ISAC) where he served for five years and former Board member for the Financial Services Information Sharing & Analysis Center (FSISAC). Jim is the Chief Trust Officer for Saviynt. Jim is a former CSO/CISO for American Express, DTCC, KPMG, Aetna, CVS and MassMutual. Jim brings to the boards and senior executives a vast business and technology background and is considered a digital and cyber security industry expert and thought leader. Jim is currently an advisor for Wiz, Transmit Security, Netskope, Armis, Security Scorecard, Devo, Gurucul, Data Theorem, CalypsoAI, CodeZero, Picnic, and Legit Security. He serves in an advisory capacity and investor for cyber specific venture funds including Syn Ventures, CyberStarts, Security Leadership Capital, Ballistic Ventures and Rain Capital. Jim is an ICIT Fellow and an Adjunct Faculty member where he teaches cybersecurity for the NYU Tandon School of Engineering. Jim also mentors over 70 cybersecurity leaders and potential leaders.

Lawrence Lepard

Is the founder of Equity Management Associates LLC, which was founded in 2006.
He is currently an Independent Non-Executive Director at Amarillo Gold Corp., an Independent Director at Rise Gold Corp., a Director at Cabral Gold, Inc., an Independent Director at Lavras Gold Corp., and a Limited Partner at Johns Creek Partners LLC.
Mr. Lepard's former jobs include being a Director at Axel Springer Norway AS, a Partner at Summit Partners LP from 1984 to 1991, an Investment Associate at Continental Illinois Venture Corp., a Financial Analyst at Citigroup Global Markets, Inc. (Broker), a Principal at The Cue Ball Group LLC, and a Managing General Partner at Geocapital Partners LLC from 1992 to 2005.
He also worked as a Financial Analyst at Smith Barney Harris Upham & Co., Inc. Mr. Lepard received his undergraduate degree from Colgate University in 1979 and his MBA from Harvard Business School.

Aron J. Ain
Executive chair of the UKG Board of Directors

Aron J. Ain serves as executive chair of the UKG Board of Directors as well as operating partner at Hellman & Friedman (H&F). Aron firmly believes that great businesses are powered by great people, anything is possible when people are inspired at work and in life, and great management is the single-largest business component that adds to shareholder value and company performance.
Before transitioning into both the UKG executive chair and H&F roles in 2022, Aron served as longtime CEO of UKG. Aron joined Kronos Incorporated in 1979 and held a role in nearly every functional department over the years, working his way up to become CEO in 2005. In 2020, as founding UKG CEO, Aron helped lead the merger between Kronos and Ultimate Software to become UKG amid the COVID-19 pandemic. The following year, UKG made history by becoming the first newly merged entity to land on the Fortune 100 Best Companies to Work For® list, debuting at #6.
Aron is a multiple-time honoree on Glassdoor’s Top CEOs list and is regarded as a pioneer in workforce management and human capital management. In 2018, Aron released his debut book, “WorkInspired: How to Build an Organization Where Everyone Loves to Work” (McGraw-Hill Education), which chronicles how he and the company’s leadership team used employee engagement as a business strategy to impart leadership lessons onto senior leaders, HR professionals, and people managers.

Virginia M. (Ginni) Rometty
Former Chairman, President, and CEO of IBM, Co-Chair at OneTen, and author of Good Power.

Ginni is a leader, innovator, and convener who believes that how we work and lead is as important as what we achieve. As the ninth Chairman, President, and CEO of IBM, Ginni transformed the 100-year-old company, reinventing 50 percent of its portfolio, building a $25 billion hybrid cloud business, and establishing IBM’s leadership in AI and quantum computing. She drove record results in diversity and inclusion and supported the explosive growth of an innovative high school program, P-TECH, to prepare the workforce of the future in more than twenty-eight countries. Through her work with the Business Roundtable, she helped redefine the purpose of the corporation.

Today, she is a champion of SkillsFirst learning, hiring, and advancement—a movement to connect more people without college degrees with good jobs. In 2020, she co-founded OneTen, a coalition of companies and educators committed to upskilling, hiring, and promoting one million Black Americans without four-year degrees by 2030 into family-sustaining jobs and careers.

She is the author of the bestselling book Good Power: Leading Positive Change in Our Lives, Work, and World (Harvard Business Review Press), a moving combination of memoir, leadership lessons, and big ideas. The book shares milestones from her life and career while redefining power as a way to drive meaningful change in positive ways for ourselves, our organizations, and for the many, not just the few—a concept she calls “good power.”

Ginni serves on multiple boards, including JPMorgan Chase and Memorial Sloan Kettering Cancer Center, and was named Fortune’s #1 Most Powerful Woman three years in a row. She has been honored with the designation of Officier in the French Légion d’Honneur and is a member of the National Academy of Engineering.

Her bestselling book, Good Power: Creating Positive Change in Our Lives, Work, and World, offers leadership lessons through the lens of her life and career.

Pioneers and Legends
sEASON TWO KICKOFF
DECEMBER 9, 2024

Hosted by: John Calamia, Founder, President, Oak Point Consulting Randy Seidl, Founder, Sales Community, Co-Founder, Pioneers and Legends, Les Rechan, Executive Chairman, Lorica Cybersecurity, Board Member, Microstrategy, Co-Founder, Pioneers and Legends

Guest Speaker:
Aron J. Ain, Executive Chairman of UKG and Former CEO of UKG

Season Two Kick-off Attendees: (partial list)

Alex Pinchev, Managing Partner, Capri Ventures, Board Member

Eric Sigurdson, Executive, Russell Reynolds

Jeff Delaney, Vice President of Engineering, Black Duck

Gary Glouner, Venture Advisor, GBD Ventures

Les Rechan - Four-time tech CXO, IBM, Oracle, Board Member

Mark Logan - Chief Executive Officer, One Identity

John Spiliotis, GTM Advisor/Board Member NetSPI

Debbie Peterson - Vice President, CallMinor

Steve Biondi - Lenovo, Head of Channels and Alliances

Mike Sullivan, President, Global Field Operations, Phosphorus Cyber

Satish Khatu, Public Board Member, Former General Manager IBM

Michael Trusner, Senior Sales Executive, UKG

Steve Shauck, Chief Revenue Officer, Analytics8

Scott Sunday - Chief Customer Officer, BigID

Marcus Peperzak, Chairman/Co-Founder at Aurora Organic Diary

Tatiana Piloto, SaaS Executive, Board Member, Country Mgr., Advisor

Rita Patel Jackson, SVP Product Marketing, Open Text

Steve Gregorio - High tech CFO, Board Member, Advisor

Victor Sachs, SVP, First Advantage, Former VP, Salesforce, HP

Josh Cohen - Former Head of Sales, Iterative

Nicole Lieberman, Senior Vice President, W3LL

Mayer Levitt, President, Jodena Consulting

Toby Paul, Board Member, Director, Strategy, Procore

Fred Luconi, Founder, Index Systems, Board Member, Artist

Melissa Sloan, Vice President, Bank of America, Chief Strategy Officer

Frank Palumbo, Former CRO, AMD Pensando, SVP Cisco

Pioneers and Legends
Season ONE Finale
April 18, 2024

Hosted by: Randy Seidl, President, Sales Community

Event Speakers - Founder - John Calamia, President, Oak Point Consulting and Les Rechan, Co-Founder, Five-time CXO and Board Member

Legendary Guest Speakers:

Bill Seibel

Five-time CEO, Founder, Serial Entrepreneur

James Routh

Five-time, CSO/CISO, cybersecurity industry expert and though leader

Larry Lepard

Leading industry expert on Cryptocurrency and alternative asset management.

Attendees:

Jim Bowman, Co-Founder, Velosio, Ed Lando, SVP, Lando and Associates, Rick Snyder, Board Member, Cisco, Alex Pinchev, Founder, Capri Ventures, Art Allen, CEO, Adaptive Computing, Andrea Gasior, Vice President, Dell Technologies, George Marks, CEO, Session Guardian, Eric Sigurdson, Partner, Russell Reynolds, Nicole Geller, Martek Global Services,Scott Kelly, VP, Product Management, Chronosphere, Barbara Steinberg, CEO, E-Fraud Services, George Stasiw, President, Q-Point Services, Jim Murphy, RVP, Nexthink, Dave Carlquist, Executive Coach, Chris Riley, CEO, Winning Edge LLC