The Power of
Community
Where relationships are built
and legends share their stories.
Why Join
Pioneers and Legends?
At Pioneers and Legends, everything we do is built on one word: Community.
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In business and in life, your network determines your net worth—not just in capital, but in the depth of your relationships and the lives you touch. We are a membership organization defined by shared values and a collective mission: to leverage our experiences to empower the next generation.
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By bringing together the legends of corporate America to share their stories, we provide our members a rare space to grow, connect, and give back.
Join our efforts to turn individual successes into collective impact.
What Our Membership Includes
Access to an entire season of our member-only in-person and virtual events throughout the year. These include Fireside Chat Sessions with legends, Topical Workshop Sessions, Community Activities, Networking Sessions, and Roundtables covering a wide range of areas of interest to our members. ​
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Ability to bring a plus-one to all events.
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Full Access to the Pioneers and Legends community through our own special internal communications channel, where members can reach out to others for help and guidance on a variety of topics.
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Access to our monthly newsletter featuring career opportunities, activities with local partners, topical discussions on matters of technology, and community give-back programs.
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Regular one-on-one membership support: check-ins tailored to your goals, challenges, and priorities.
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Career guidance, job opportunities, board membership, referrals, and industry insights provided by our members, and access to resources.
Becoming a Member
There are two ways to become a member: via invitation or via interview. Because we care about quality, our founder personally vets every prospective member. To schedule an interview, please use the button below.
The Ways We Connect
Fireside Chats
Our legends share their experience and expertise on a wide range of technology and leadership topics. Guests spend the evening answering questions and sharing one-on-one experiences with our members.
Networking Sessions
Networking is a key objective for us. We host icebreaker activities and themed discussion groups to foster meaningful interactions between members.
Topical Workshops
We host 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
We promote community building through local social and economic programs aimed at improving the overall welfare of the community, including job opportunities and advanced skills training.
We also work with affiliated partners to support their respective efforts.
Why Join Pioneers and Legends
"Pioneers and Legends is a terrific resource that one can only find in Naples - the range of business leaders we saw last year was amazing. And being able to see them in a 'home' setting along with a small crowd of interested people - incredible."
- Cliff Elam, SVP and Head of Sales of Solutions by Text
"Welcome new members! You're going to love these sessions! Excited for the fall to connect with all of you."
- Michele Schauk, Global Sr Director of Success and Support, Timeless Medical Systems
