Our Mission

the power of community

We are a business community of current and former leaders bringing together professionals, enthusiasts, entrepreneurs, and investors interested in technology and innovation.

Our members are current and former technology and corporate America executives. Executives are from companies such as Oracle, IBM, PTC, Dell, EMC, UKG, Tivoli, Red Hat, ASG, Sun Microsystems, Hewlett-Packard, Microsoft, Gartner, ACI Worldwide, Facebook, Informatica, and BMC.
Fireside chat sessions: Our guests share their experience and expertise on a wide range of technology and leadership topics. Guests spend the evening answering their questions and sharing one-on-one experiences with our members.
Networking Sessions: A major objective is the networking aspect. Icebreaker activities and themed discussion groups can help break the ice and foster meaningful interactions.
Topical Workshop Sessions: Weekly luncheons covering a wide range of topics including AI, Cybersecurity, career and talent assessment, sales leadership, executive leadership, Board level roles and responsibilities.
Community Activities: Encourage community building through local social and economic programs aimed at improving the overall welfare of the community including jobs and advanced skills training. We encourage working with affiliated partners in support of their respective efforts.
Pioneers and Legends was formed in Naples, Florida and is our home base of operations.

FOUNDERS

Our Founders

the power of community

John P. Calamia
Founder

John is Founder and President of Oak Point Consulting. His firm is focused on executive search and career consulting. He has completed hundreds of searches helping companies build GTM teams throughout North America. Prior to entering into executive search, John held several sales leadership positions playing a pivotal role in three initial public offerings including Sybase, Vignette, and Riversoft. He maintains residences in Westhampton, NY 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.

Pioneers - Summer at Chatham Bars Inn

Guest Speaker

Ben Pring

Speaker/Author/Advisor

Former Vice President, Gartner

Date: August 20, 2025

and several surprise guests to be announced

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”.

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.

Jeffrey O. Henley
Vice Chairman, Oracle Corporation

Jeffrey O. Henley is vice chairman of Oracle Corporation. He served as Oracle's chief financial officer and executive vice president from 1991 to 1995. He was chairman of Oracle from 2004 to 2014. He also serves on Oracle's Executive Management Committee.

Prior to joining Oracle in 1991, Henley service as executive vice president and chief financial officer at Pacific Holding Company, a privately held company with diversified interests in manufacturing and real estate, and as executive vice president and chief financial officer at Saga Corporation, a multibillion-dollar food service company.

Mr. Henley is chair for the Institute for Energy Efficiency at UC Santa Barbars. He also serves on the advisory board for the Dean of Engineering at the university.

Jeff has a BA in economics from the University of California at Santa Barbara and an MBA in finance from UCLA.

Linda Jojo
Frmr. Executive Vice President and Chief Customer Officer United Airlines

Linda Jojo served as Executive Vice President and Chief Customer Officer of United Airlines from 2022 to 2024, after serving as Chief Digital Officer and Chief Information Officer from 2014 to 2022. During her tenure, she transformed the use of technology at the airline for both employees and customers, improving the day-of-travel experience with multiple industry-first tools and services. She and her teams created unique customer experiences by combining physical airport design with personalized technology and driving innovation, such as AI-driven customer messaging and call center experiences, as well as sophisticated operations and commercial tools.

Prior to joining United in 2014, Linda held the most senior executive position in technology at Rogers Communications, Canada’s leading wireless, cable, and media company, as well as at Energy Future Holdings Corporation and Flowserve Corporation, both in Dallas, TX. Earlier in her career, she worked for GE in various technology leadership roles.

She currently serves on the board of directors at Exelon Corporation, Hero Digital, and the Federal Reserve Bank of Chicago.

Linda is passionate about preparing young people for STEM careers. She is the immediate past chair of the Board of Trustees of the Adler Planetarium in Chicago and a member of the Board of Trustees at Rensselaer Polytechnic Institute in Troy, NY.

Linda holds a bachelor’s degree in computer science and a master’s degree in industrial engineering from Rensselaer Polytechnic Institute.

Ben Pring
A winner of Gartner’s prestigious annual Thought Leader award, a Bilderberg Meeting participant, a member of the advisory board of the Labor and Work Life program at Harvard Law School. Named as one of the 30 leading management thinkers by Thinkers 50 and one of the 10 leading influencers on the future of work by Onalytica.

Co-author of the best-selling and award-winning books, What to Do When Machines Do Everything - Code Halos: How the Digital Lives of People, Things, and Organizations are Changing the Rules of Business - Monster: Taming the Machines that Rule Our Lives, Jobs, and Future (which was a Financial Times Book of the Month), and Certain Uncertainty: Leading With Agility and Resilience in an Unpredictable World.

Ben’s work has been covered in major publications such as Harvard Business Review, Wall Street Journal, Financial Times, London Times, BBC’s News Night, BBC World Service, PBS’s News Hour, NPR’s On Point, Drucker Report, and MIT Review.

Ben is a resident of Cape Cod, Massachusetts. For additional information please visit www.benpring.com

Screenshot_2-7-2025_92325_www.benpring.com.jpeg

Pioneers and Legends
April Event
April 8th, 2025

Hosted by: Eric Sigurdson, CIO Practice Leader, Russell Reynolds, John P. Calamia, Founder, Pioneers and Legends, President, Oak Point, Randy Seidl, Founder, Sales Community, Co-Founder, Pioneers and Legends, Les Rechan, Executive Chairman, Lorica Cybersecurity, Board Member, Microstrategy, Co-Founder, Pioneers and Legends.

Attendees: (partial list) Jim Bowman, Frmr. Chairman, Velosio, Maureen Osborne, Frmr. Corporate VP, Microsoft, Michael George, CEO, Syncro, Adam Sewall, CEO, Waterleaf , Jeff Rodek, Frmr. Chairman, Hyperion, Bill Berutti, Chairman, Presidio, Bill Seibel, Frmr. CEO Mobiquity, 5x CEO, Aron Ain, Frmr. Chairman, CEO, UKG Technologies, Fima Katz, CEO, EltegraAI, Scott Sunday, Chief Customer Officer, BigID, Steve Shauck, Chief Revenue Officer, Analytics8, Naomi Kent, CEO, The Boardroom Company, Inna Kuznetsova, CEO, Toolsgroup

Guest Speaker:
Linda Jojo, Executive Vice President and Chief Customer Officer, United Airlines

Pioneers and Legends
February Event
February 18, 2025

Hosted by: John P. Calamia, Founder, Pioneers and Legends, President, Oak Point, 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:
Jeffrey Henley, Vice Chairman, Oracle Corporation

February Attendees (Partial List)

Jeff Delaney, Vice President of Engineering, Black Duck

Andy Kofoid, President, Databricks

Buel Duncan, Frmr. VP, Marketing IBM

Adam Sewall, CEO, Cyberleaf,

Jeff Rodek, Frmr CEO, Chairman , Hyperion

Dan Dufault, Frmr. Senior Vice President, Info

Chris Riley, Frmr. President, Datarobot

Bill Berutti, Frmr. President, BMC, SVP, PTC

Dave Micalizzi, Frmr. Vice President Client Services, Mobiquity

Ed Lando, Frmr Head of Talent, Veeam

Ed McLaughlin, Chief Technology Officer, Ansira

Frank Palumbo, Frmr, Senior Vice President, Cisco

Mark Atherton, Head of Financial Applications, Oracle

Jim Bowman, Frmr Chief Executive Officer, SBS Group

Tom Reinsel, Frmr. Director of Sales, Okta

Jonathan Elmer, CISO, Meditology Services

Lawrence Lepard, Managing Partner, Equity Management

Dave Carlquist, Frmr. Vice President, Global Strategy, IBM

Randal Narike, Executive Vice President, Enterprise Holdings

Tom Weaver, Frmr. Executive Vice President, Computer Aid

Dave Samuels, DrFirst - Chief Financial Officer

Eric Sigurdson, Managing Partner, Russell Reynolds

Joel Glasky, Head of Capital Markets, Financ

Aron Ain, Vice Chairman, UKG, Former CEO, Kronos/UKG

Rita Patel Jackson, SVP Product Marketing, Open Text

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

Tom Driscoll, Investor, Advisor, Board Member

Rick Scurfield, Chief Revenue Officer, VAST Data

Toby Paul, Board Member, Director, Strategy, Procore

Jim Routh, Chief Trust Officer, Saviynt, 5x CISO

Inna Kuznetsova, Chief Executive Officer, Toolsgroup

Bill Seibel, Strategic Advisor, PlateRate, Serial Entrepreneur

Pioneers and Legends
January Event
January 16, 2025

Guest Speaker:
Ginni Rometty, Former Chairman, President and CEO of IBM

January Attendees (Partial List)

David Hunt, CEO, Ensemble LLC

Andrea Gasior, Sales Advisory Board Member

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

Joel Glasky, Head of Capital Markets, Financo

Debbie Peterson - Vice President, CallMinor

Steve Biondi - Lenovo, Head of Channels and Alliances

Aron Ain, Vice Chairman, UKG, Former CEO

Satish Khatu, Public Board Member, Former General Manager IBM

Adrian Karaboutis, Corporate Board Member

Steve Shauck, Chief Revenue Officer, Analytics8

Kark Soderlund, Senior Vice President, Zscaler

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

Tom Driscoll, Investor, Advisor, Board Member

Rick Scurfield, Chief Revenue Officer, VAST Data

Cristina Roa Marks, Vice President, SessionGuardian

Toby Paul, Board Member, Director, Strategy, Procore

Glenn Turner, CEO, Founder, Romeo Bravo Software

Craig Tobin, CEO, Ascent Business Partners

Jim Routh, Chief Trust Officer, Saviynt

Inna Kuznetsova, Chief Executive Officer, Toolsgroup

Edison Peres, Board Member, NWN Carousel

Bill Seibel, Strategic Advisor, PlateRate

Paul Fiumano, Chief Executive Officer, Intelligent Net Yield

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