How to scale business operations with AI

Jordan Mix isn't just running one company with AI - he's running six. As an operating partner at Late Checkout, Jordan oversees a diverse portfolio of businesses, all powered by community and AI automation.

In our latest live workshop, Jordan pulled back the curtain on how Late Checkout uses generative AI to streamline operations across their holdings. From applicant tracking to podcast archives, Jordan demonstrated how they're leveraging AI to work smarter, not harder.

The workshop is a great watch for anyone looking to scale their operations, automate repetitive tasks, or make better use of AI in their daily work.

Here's a quick summary of the session with Jordan:

Experimental mindset is key

Jordan emphasized the importance of an experimental approach when it comes to AI tools:

"We experiment, see what works and implement. This is an experimental phase. You just have to be trying new tools,” he advised. “It's annoying to sign up for a bunch of different tools to use them for two days or never. But those reps and experiments help you figure out what to implement into your system.”

He acknowledged that constantly testing new tools can lead to "AI fatigue", but stressed that those experiments are crucial for knowing what to actually implement long-term. This approach allows Late Checkout to stay at the cutting edge, quickly identifying and implementing the most effective AI tools and strategies.

Automating the hiring process

An impressive workflow Jordan shared was Late Checkout's applicant tracking system. Using a combination of Typeform, Notion, Claude, and ChatGPT, they've created a seamless process for reviewing applicants.

“We have tons of people applying for roles across our various companies. It was becoming hazardous how we were keeping up with applicants. We used Notion as the central database and had automations set up, but the candidate review phase was really clunky. Inconsistent resumes, loom videos to review, and not knowing who or how to prioritise based on the best fit for a role or a potential future role… So we created a system to remove the human from the process without affecting performance.”

Jordan walked us through their workflow of Typeform, Notion, ChatGPT, Claude and Sana and how they all combine to become a powerful applicant reviewing system. The system automatically parses resumes, identifies key information, and provides structured data in Notion. Ultimately this frees up the HR team to focus on high-level decision making.

Automating a business ideas database

On the Startup Ideas podcast, host Greg Isenberg talks about 4-5 new business ideas twice a week with different guests. Jordan and the team thought it’d be a good idea to keep track of all the most viable ideas in a database for 3 reasons:

1. It makes for a cool resource that other people can use.
2. They can add it to Claude Artifacts as knowledge, which is helpful for things like when they want to jam with Claude on sourcing an acquisition or thinking of new business ideas.
3. It’s a really good lead magnet that's driven significant newsletter growth.

During the workshop, Jordan showed us how their tech stack uses automation and AI to watch the YouTube podcast recordings, extract the transcript, and then parse the relevant text into the database in Airtable.

AI-powered sales prospecting

Perhaps the most impressive demo was Late Checkout's custom LinkedIn sales prospecting tool. Built on Airtable, it allows users to:

• Import leads from LinkedIn Sales Navigator
• Automatically enrich data with emails and phone numbers
• Generate personalized outreach messages
• Track outreach stages

As he walked us through how the tool works in real time, Jordan explained:

“What if I told you I could send you 1000s of leads in your target? And also said you could:

• look at their LinkedIn directly
• rate the quality
• get their email and phone number
• and draft an outreach message?

We built exactly this with LinkedIn Sales Navigator and Airtable. We do a ton of content. People like a lot of the content, but they might not follow us or might not book a call so this tool helps us follow up and generate tons of leads.”

This tool bridges the gap between content marketing and direct sales outreach, allowing Late Checkout to more effectively nurture leads into becoming users.

The power of "wrapping the wrappers"

When discussing future ideas, Jordan hit on an interesting concept - "wrapping the wrappers":

"I just thought, is there an opportunity to basically create a simple front-end interface that goes and leverages these models? All this cool AI stuff is quite prohibitive to the mass population. So how do you wrap it up in an interface that is approachable?”

The idea is to create user-friendly interfaces that combine multiple AI models and tools, making advanced AI capabilities accessible to less technical users. It's an intriguing vision for how AI might be democratized in the near future.

If Jordan’s workflows and ideas have piqued your interest, go watch the full workshop recording (available exclusively to our Pro subscribers).

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