AI Investable Tools and Future-Proof Strategies with Andrew Johnston of Superhuman (Part 2)

Ryan speaks with Andrew Johnston the head of sales at Superhuman for a second time, to explore the landscape of AI tools. Andrew shares his unique perspective on what makes an investable AI company, the importance of seamless integration and workflow, and the future of AI.

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  • AI agents and chatbots are limited in their effectiveness unless they are built with seamless integration and have their own unique value as part of the chain within AI.
  • Successful AI tools have integrated in a smart way, with 75% of their own built IP or workflow and 25% leveraging LLMs or fine-tuned data.
  • Security is a huge concern in the AI space, and tools like Liminal AI are addressing this by enabling secure use of LLMs within highly regulated institutions.
  • RevOps teams can benefit from AI tools like Cinch, which enable sales leaders to build dashboards, reports, and alerts using natural language and prompting.
  • AI research tools like Agent Herbie bring resources directly to the user’s email, making market analysis more accessible for sales reps and marketers.
  • Microsoft is going deep on AI integration across their entire stack, including a proactive team copilot and AI capabilities built into PCs.
  • When investing in AI companies, distribution and go-to-market strategy are key differentiators, along with good UI/UX design and core software fundamentals.
  • The simplest AI use cases that save 10-30 minutes of time and deliver clear outcomes are often the most powerful and effective tools for CEOs and CROs.


“What I try to look for is for companies that have integrated in a smart way, but have built a unique IP or workflow so that it’s more like 75 per cent of what they’ve built.”

“I think what’s important is two things. One is. If you’re going to invest in a tool or you’re going to find a tool that you use, like, does it get you to an outcome or is it just a chatbot?”

“Distribution is key. You know, who’s your market, who you’re going after, why is the product sticky? I think that’s really, really important to think through.”


Ryan Staley

Founder and CEO

Whale Boss 

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: