If you hand AI strategy to a manager, you’ll get automation. Not transformation.
Most founders are approaching AI the same way they approached their CRM rollout, their marketing automation platform, and their new reporting dashboard. They find a smart manager, hand them the tools, and say: “Go find some efficiency.” Wrong move.
Last month at our Sundance retreat, I watched a room full of founders have the same realization at the same time. We had been talking about lead generation. Specifically, why outbound feels so broken for boutique professional services firms. The room was nodding. Everyone had tried some version of the same playbook: buy a list, write a template, blast it out, hope for replies.
When Collective 54 launched, we couldn’t host in-person events. The pandemic made sure of that.
So we built everything virtually. And it worked. But something was missing.
In 2023, we hosted our first in-person gathering for the full membership. We called it the Founders Summit. It’s now in its fourth year, renamed the Member Reunion, and it draws 200 members.
Most of us feel overawed where to place our AI bets. I’ve definitely felt uncertainty making some calls, so I empathize a lot with fellow C54 members being hit from all angles… However, I luckily have a fool-proof methodology that will make us all millions more dollars!!!
Over the last several weeks, I’ve found myself in a familiar place with a number of founders we work with and some as members of this community. The plans are done. The year is underway. Teams are executing.
In today’s crowded marketplace, expertise alone is not enough to stand out. Every competitor has case studies, service offerings, and smart people on staff. What sets the leaders apart from the rest is their ability to translate insight into authority. The firms and executives who become the “go-to” voices in their market are those who consistently share perspective, shape the narrative, and earn the trust of decision-makers at the highest levels.
A room full of members walked into a workshop in Sundance, Utah last month. They weren’t there to learn about AI. They were there to fix their pipelines.
These weren’t founders sitting on the sidelines. They were pioneers. Members of Collective 54 who had already committed to becoming Era 3 AI firms. They didn’t need convincing. They didn’t need a hype session. They wanted help getting started and getting it right.
To drive real results, AI can’t be something you dabble with randomly. It has to attach to re-al friction in your day-to-day work, or it turns into “you tried ChatGPT for a week” and moved on.
We just got back from our first workshop style retreat in Sundance, Utah.
We brought ~30 members together for two days of deep work.
The focus: lead generation and deal management using AI native tools.
After two packed days, one insight kept coming back up.
AI handles the lower value tasks so humans can focus on the higher value work.
In the boutique consulting world, you hire the best minds, wrap them in a methodology, and sell their time as the delivery vehicle for specialized knowledge. At SureStep, we spent 15 years doing exactly that—providing high-level GRC and technical expertise to companies around the world.