20+ Years Experience
We’re more than just advisors—we’re experienced professionals who’ve survived and thrived through the impact of technology over the last 20 years.
Managing Partners
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Steve Mast | Strategy
Steve has over 25+ years of building and selling technology businesses and has thrived on helping organizations transform their business models to meet today’s modern demands. Steve has served as President, Chief Innovation Officer and Chief Product Officer at various digital marketing, research and technology firms. His focus is on creating environments where clients and teams can play, learn, and grow together. Steve’s philosophy is simple—success is measured by actions, not words.
Laura Craig | Research
Laura Craig is a dynamic strategic director with a 25+ year rich background in product innovation, strategy, and customer insight. She has over 20 years of experience, including roles as SVP Product Innovation at Sago, VP at Ipsos, and owner of a boutique research agency. After identifying a client need to scale qualitative interviews, Laura co-founded CRIS, a groundbreaking AI-enabled virtual moderator. Laura excels in harnessing technology to enable agile decision making and creating environments where clients and teams can thrive.
Ross McLean | Education
Ross is a 25+ year seasoned professional in brand strategy, consumer insight, and creative technology application with a focus on generative AI. Ross has studied AI Leadership & Strategy, Advanced Prompt Engineering and AI-related Change Management at Vanderbilt University and DeepLearning.AI. Prior to his AI- Deep Dive, Ross founded the Over the Shoulder Smartphone Ethnography platform and was EVP and Director of Strategic Planning at Foote Cone & Belding Chicago, leading strategy for brands like Kraft Mac & Cheese and Coors Light. Ross played a pivotal role in FCB’s transformation from traditional to digital.
Randall Matheson | Innovation
Randall Matheson is an innovation strategist with a 25+ year proven track record of turning ideas into digital products. He specializes in working with Generative AI for content creation and using cutting-edge AI tools to create and interact with virtual audiences. Recently, Randy completed AI programs from IBM, Vanderbilt, and DeepLearning,.AI underscoring his commitment to staying ahead in innovation.
Suzanne Costa | Head of Twenty44 UK
Heidi Dickert | Associate
Heidi Dickert helps business leaders uncover practical AI workflows that enhance efficiency, unlock deeper insights, and create new value. As a consultant for Twenty44, she guides companies in turning the pressure and noise around AI into a clear plan of action.
Her perspective is shaped by years of working within a variety of industries, including Finance, CPG, Healthcare, and Technology. This background gives her a firsthand understanding of the unique workflows and business challenges different sectors face.
Heidi’s approach is grounded in her deep specialization in market research. This experience, honed on both the client and supplier side, gives her a distinct ability to start with the core business questions for any new initiative. It ensures that the adoption of AI is not just about technology, but defining the most impactful business use cases to achieve measurable results.
She helps leaders identify the right opportunities to use AI for the biggest impact and move their organizations from AI-curiosity to genuine capability. Her focus is not about replacing human expertise, but amplifying it.