Collaborative Gain
20 Years - Leaders Helping Leaders

Leaders
helping
Leaders.

With AI and everything else

Since the dawn of the web and through the age of AI, we’ve brought you the team. We’ve curated a community where leaders help each other evolve, innovate, and build modern organizations.

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Explore Councils

20+yr

Helping leaders

7+yr

Avg. member tenure

92/93

NPS — Moderator / Trust

Members lead at companies including

  • Amazon
  • Microsoft
  • Adobe
  • Intrinsic
  • Square
  • JP Morgan Chase
  • Capital One
  • Peloton
  • Klaviyo
  • Fidelity Investments
  • Warner Bros
  • Ontra
  • Estee Lauder
  • Wells Fargo
  • Target 
  • Pepsi 
  • Google
What’s included

Three layers of support.
One trusted community.

Your team: a council of peers, an executive coach, and the broader CG community. ​

The Core Layer

Your Council

  • 10–15 peers. Non-competing leaders across different industries, company sizes, and stages. Diversity of context is intentional and magic.
  • Virtual meetings throughout the year to build trust and work through what’s live.
  • In-person retreats with an agenda crafted from 1:1 interviews with every member.
  • Led by a professional moderator with deep industry experience.
Year-Round

Your Community

  • Peer Coaching Calls: a structured call for your stickiest question with the right peers across Collaborative Gain.
  • CG Life: Throughout the year, members gather for casual dinners, happy hours, small-group meetups, occasional regional or travel-based gatherings.
  • Roundtables: ongoing, small-group conversations around shared topics or identities. These combine tactical support, advice, and connection.
1:1 Thought Partner

Your Coach

  • 1:1 coach assigned to every member, accountability partner, sounding board, thinking space.
  • Knows the community intimately and plugs you into the right peers, calls, and councils.
  • Ensures you actually get the value of the membership, not just access to it.
In their own words

Hear from members who’ve lived it.

Members telling the story, in their own words, of why they keep coming back.

CG is the best source of guidance and counsel I have received as a leader. When I am stuck with a professional or personal problem, the Collaborative Gain community of smart peers and career coaches have provided insights and potential solutions, from relevant experience, that have helped me navigate my professional journey. This is a wonderful community of amazing leaders.

Andy Cerio, Managing Director — Global Engineering Experiences
J.P.Morgan Chase & Co.

I wish I would have found Collaborative Gain 10 years ago. It would have accelerated all of the peer learning I was trying to do ad-hoc at conferences.

Jen Loy, Director, Product Design
CDW

I have been a Product executive for years and only recently learned about Collaborative Gain. I have found immense value in the forum’s connections and insights. CG prioritizes talented leaders and emphasizes human connection. It is rare to find the authenticity and vulnerability I’ve experienced so far.

Joel Haugen, Chief Product Officer
DaVita Kidney Care

Read more from our members →

Member stories

Real challenges. Real peers. Real results.

Read More
,

Almost Saying No to the Right AI Role

Ready to walk away → a better-negotiated AI role he chose with clarity

Read More
,

Getting AI Costs Under Control

Runaway AI spend → a plannable per-employee cost model

Read More
,

Rethinking a Product Career in the Age of AI

Uncertain future for product → three clear paths forward

Read more member stories
Our mission

Building your career is a team sport.

The best leaders don’t operate in isolation. They surround themselves with trusted peers, people who’ve sat in the same seat, made the same calls, and are willing to be vulnerable about what they’ve learned.

Collaborative Gain creates the small, curated, confidential environments where leaders pressure-test decisions, share what’s actually working, and grow together, season after season, promotion after promotion. Because building a career, and building the company behind it, is a team sport.

More about us →

01
Careers are built with others

Nobody gets to the top of their craft alone. The leaders we admire most have trusted peers behind them — sounding boards, sparring partners, honest friends.

02
Trust is the whole product

Small, curated cohorts. No vendors, no consultants and no ego . The room only works when people can say the thing they can’t say anywhere else.

03
Whole humans, not just operators

We care about the leader behind the title and the life behind the leader.

04
Wisdom compounds

Members stay for years, sometimes decades. Relationships deepen, patterns emerge, and the community grows richer.

What’s happening

The rhythm of the year.

In-Person Council Meetings
Fall 2026
Philadelphia, PA

Mon Oct 26 – Wed Oct 28

Spring 2027
Scottsdale, AZ

Mon, Apr 12 – Wed, Apr 14

Virtual Meetups
  • Monthly Virtual Council Calls
  • Topic-Based Roundtables
  • Peer Coaching Calls
  • Ad hoc Coaching

Join the Councils yourself.

Or level up your team. ​

Tell us who you are and what your goals are, for yourself or your organization. If there’s a way we can support you, we’ll explore it together.

Let’s talk

Completely confidential. Expect a personal response within five business days.

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