We started Big Sister AI as the opposite of “Big Brother.” Our goal was never control, it was to empower salespeople with tools they actually enjoy using. Most CRMs only tell you what happened; we wanted to explain why.
Through our concept of Sales Astrology, we analyse every sales interaction to uncover what drives performance, helping teams work smarter, close more deals, and boost their earnings.
When we joined Connectd, we were rebuilding both our team and product to take Big Sister AI to the next level. We needed experienced mentors and advisors who could guide us through scaling our technology and preparing for enterprise clients.
Through the platform, we quickly connected with the right people - experts who understood our challenges and could help shape version two of the product. It made the whole process faster, smoother, and far more effective than traditional networking.
Through Connectd, we brought on three key advisors, each focused on a specific part of our growth. Eric Callahan supports our cloud and product architecture, helping us strengthen the foundation to scale. Benjamin Schroeder leads on AI development, refining how we apply intelligence across the platform. And Ian Rotondi-Gray advises on go-to-market strategy, helping us sharpen our sales approach and prepare for seed funding.
Each advisor brings deep, hands-on expertise, and together they’ve helped us shape version two of Big Sister AI, a stronger, smarter product ready for the next stage of growth.
It’s absolutely foundational. Having advisors who’ve done it before means we can move faster, avoid mistakes, and make better decisions from the start. These people aren’t just mentors giving advice, they’re committed partners who understand our product deeply and take responsibility for the outcomes.
At our stage, it’s impossible to hire full-time executives with enterprise-level experience, but through Connectd, we’ve gained access to that calibre of expertise on a fractional basis.
It’s made a huge difference in how we build, scale, and think about the business.
We always start with our goals. Before choosing anyone, we define what success looks like for that role and the key results we want to achieve. From there, we look for people who understand those challenges, whether or not they come from our industry.
For example, our architecture advisor, Eric, doesn’t come from sales but has a background in data and sports analytics, which gave him a unique perspective on how to measure and improve performance. That mix of skills and curiosity is what matters most. It’s about finding people who care about the problem and want to help solve it.
I’d share two main pieces of advice. First, be specific. Don’t look for a general “marketing” or “sales” advisor, define exactly what you want to achieve and set clear goals or OKRs before bringing someone in. It makes conversations more focused and helps you find the right match for your needs.
Second, make time for the process. Finding the right fractional talent takes work - you’ll have multiple calls and need to prepare before each one. It’s not a quick hire, but it’s worth it. Investing that time upfront ensures you bring on people who truly add value and help you reach your next stage of growth.
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