In An AI Era, Why Small, In-Person Events Are Driving Big Deals For Executive Women

Forbes

7 hours ago

As AI reshapes business, The DealmakeHers Beach Club shows that nothing replaces the trust built through face-to-face connections — the kind that ultimately close deals.
'Do I like you and do I trust you?'
These two questions should drive every successful business deal, says Stacy Berns, communications veteran and co-founder of The DealmakeHers. Yet in an AI-dominated business environment, answering these questions is more challenging than ever.
The DealmakeHers most recent event was designed with that problem in mind. The community of female founders, executives and investors recently hosted The DealmakeHers Beach Club, a two-day meet-up at Gurney's Montauk Resort that brought together 45 C-suite leaders from brands like Ralph Lauren, Mattel and True Religion. The DealmakeHers partnered with Chase Media Solutions to provide an effective alternative to large industry conferences, offering a highly curated environment where authentic connections could naturally evolve into real business opportunities.
A Shift in the Event Landscape
For executives seeking new opportunities, the choice has been between large-scale industry trade shows or retreats focused on wellness, leadership or skill-building. Both formats serve important purposes, but neither is optimized for dealmaking.
'What I love about The DealmakeHers is that it's unapologetically 'we are here to do some business and make some deals,'' said Rebecca Minkoff, designer, entrepreneur and founder of the Female Founder Collective. 'Once that tone is set, you have the freedom to say, 'hey, I want to work with you.''
That unapologetic focus reflects a broader shift toward highly curated B2B experiences where leaders can be more discerning with their time and travel. True Religion CMO and Head of Digital Growth Kristen D'Arcy traveled from Los Angeles to New York specifically to connect with this small group of like-minded leaders. 'It's not transactional,' she said. 'I don't feel like someone is trying to sell me something every minute. Here I can make true relationships.'
Inside an Intimate Dealmaking Event
The program of The DealmakeHers Beach Club was deliberately structured to maximize attendees' time. Starting late on a Monday gave them time to complete their workday before arriving, a detail that allowed them to be fully present. 'The thing I loved was the time it started,' said Michelle Cordeiro Grant, founder and CEO of intimates brand Lively and popular beverage brand Gorgie. 'I felt like I had already had an impact with my business and team, so I could be present here.'
A guided beach meditation opened the event, empowering participants to clear their minds and set professional intentions before diving into strategic conversations.
Later that evening, a bonfire provided the backdrop for executives to share their dream collaborations and career ambitions. The aim was to create a space where women could voice their biggest professional aspirations, knowing someone in the group could likely help make them real. Some spoke of promotions, others of ideal partnerships or even retirement. 'When it's the right prompt and right environment, people feel safe,' Minkoff said. 'That's when the magic happens.'
Sarah McNamara, CMO of Peter Thomas Roth, left with concrete opportunities in motion. 'Walking away from this, I already have questions I need to answer and people I need to follow up with. There really is potential for making deals.'
The next morning began with a workout led by celebrity trainer Isaac Boots, reinforcing the connection between physical stamina and professional performance. 'Although I've been very successful at work, exercise is the area I have neglected,' said Ralph Lauren SVP of Stores Sharonda Weatherspoon. Looking around the room she added, 'But this is what 'great' looks like. This is what it means to be a professional woman and to make sure you have the stamina to bring all of your really great ideas to fruition.'
A working breakfast followed, featuring business insights from Minkoff, Kroma Wellness founder Lisa Odenweller, skincare expert Pietro Simone and Cordeiro Grant. By noon, guests were back at their desks — having fit two days of high-value connections into a short window.
How Smaller Rooms Build Bigger Bonds
The Beach Club succeeded because it removed the trappings of traditional events. There were no conference rooms, name badges or staged fireside chats. Instead, the focus was on shared experiences that encouraged openness, trust and collaboration.
'At Chase Media Solutions, we know that real business growth starts with trust,' shared Head of Sales & Partnerships Lauren Griewski. 'Partnering with The DealmakeHers gave us the opportunity to be in the same room with a remarkable group of women leaders, not just to network, but to build the kind of authentic relationships that fuel long-term partnerships.'
'This particular community really helps strengthen each other. It's really about building these long-term relationships, which are both personal as well as business,' said Sandra Campos, former CEO of PetMeds.
Rochelle Jacobs, creator of natural skincare brand June Jacobs, echoed that sentiment. 'I feel like everyone here is my friend although some of them I'm just meeting for the first time. We all lift each other up.'
Weatherspoon agreed. 'This was the event I needed and didn't know I needed. It's women helping women and putting them in places where they can meet other phenomenal women to keep that circle growing.'
A New Model for Executive Networking
In today's business environment, time is scarce and trust is invaluable. Inspiration alone is no longer enough; executives are demanding outcomes.
Events like The DealmakeHers Beach Club offer a new model for executive networking. In an era increasingly defined by AI and virtual interactions, these small, highly curated gatherings restore the personal element to business. By creating spaces where leaders can look one another in the eye and answer the questions 'Do I like you?' and 'Do I trust you?', they lay the foundation for authentic relationships that can lead to lucrative partnerships.