This month was a hands-on look at automations — what they are, which tools to start with, and a stack of real, copy-it-today examples for reclaiming hours every week. We closed with a timely legal note on AI and privacy from one of our working-group attorneys.

Welcome & housekeeping

Sarah Gudeman (BranchPattern, Omaha) opened with a reminder of how this community started — "by accident" — and how fast it's grown, fueled by smart people and a field that won't sit still. Ivy ran housekeeping: monthly recaps now live on the refreshed website, registration for next month is open, and a member poll is live so the group can help steer where we go next. As always, we're here to facilitate and act as a resource — member feedback drives the agenda.

This month's speaker: Kaitlyn Study

Kaitlyn owns South Street & Co., a digital marketing agency for home services and attorneys that she founded in 2015, and now also runs a company focused on helping businesses automate with AI. Fully self-taught, her origin story will sound familiar to anyone who's tried to "clone themselves": after her in-person right hand left for a dream job, a friend pointed her to Zapier — and she dove into automation out of pure necessity.

What an automation actually is

At its simplest: if this happens, then these things happen. The first step is a trigger; everything after is a series of actions. Kaitlyn's analogy is a grilled cheese — two programs that don't normally talk to each other are the bread, and a tool like Zapier, Make, or n8n is the cheese that lets them speak into one tidy sandwich.

The toolbox — and when to reach for each

• Zapier — the best place to start: the most connections to well-known apps, very user-friendly, with ready lists of triggers and actions. Check zapier.com/apps to see whether your tools integrate. Monthly plans cap how many tasks you can run.
• Make.com — comparable and also beginner-friendly; slightly fewer connections to well-known apps.
• n8n — developer-level and far more powerful, "the Wild West." With a coder on your team you can build almost anything, run unlimited automations, and self-host. More complex, but a game-changer for multi-step work.
• HighLevel — an all-in-one CRM (similar to HubSpot) with deep built-in automations and landing pages. A solid first CRM. (Kaitlyn cited roughly $99/mo — verify current pricing.)

Many tools you already use — project management like Asana or monday.com, plus industry-specific software — now build in automations and AI too.

The hidden cost of manual work

In a single month, Kaitlyn's team automated nearly 9,000 tasks in Zapier. Her back-of-napkin math: roughly ~8,890 tasks, about ~12 days of time saved (at 2 minutes per task), and around ~$17,000 of value (at her $175/hour rate) — in one month.

These are Kaitlyn's own estimates for her agency, shared to illustrate the upside. Your numbers will differ.

Think of it as building a digital assistant

The framing that matters: automation isn't about replacing people — it's about enhancing the team you have so they can focus on higher-level work. Before you hire, ask what you'd hand a virtual assistant. Most of it doesn't require judgment, just a repeatable process. Kaitlyn groups these into "assistants" you can build:

• Research assistant — research companies and prospects before a meeting (tech stack, social presence, employee count, website opportunities). She even has one that summarizes new podcast episodes into a 60-second voice rundown with a link back to the full episode.
• Admin assistant — capture meeting notes via a notetaker like Fireflies or Otter, turn them into follow-up emails, auto-assign action items in your PM tool or Slack, update client records, and send reminders to cut no-shows.
• Operations coordinator — move data between systems. Her very first automation simply pushed new WordPress posts to a social scheduler; now AI summarizes the post, pulls one action item, and drops a draft for her to review — "90% of the way there."

Four automations you can copy today

Hard-won tip: to connect ChatGPT, Claude, or Gemini to an automation platform, you must use the model's API — the consumer app (your logged-in chat, custom GPTs, prior conversations) does not link to Zapier/Make/n8n. That means a separate API account with its own billing, on top of your paid subscription. Kaitlyn lost ~8 hours learning this the hard way. Also note: Zapier's built-in "AI by Zapier" is great for one small thing, but not for long-form generation — use a full model's API for that.

How to find your own first automation

Kaitlyn's filter for spotting candidates — every copy-and-paste is a clue:

• Is it repetitive? Anything you or the team do over and over, often just out of habit. If you time-track — her agency uses Toggl (Harvest is another option) — review your timesheet to spot it.
• Is it rules-based? The logic doesn't change. This is the key one — e.g., a consistent calendar naming convention is what lets an automation file things correctly.
• Is it time-sensitive? Things due on a cadence (every Friday at noon) where a Slack/Teams/email nudge buys back brain space.

A few crowd-sourced starting points from the chat: follow-up emails, expense reports (Ivy's current mission), event/association email alerts, employee connection notes, and account research before meetings (a tool like BuiltWith can pull a site's tech stack and company details — though very small companies may return little). And don't start from zero: brainstorm and even draft the build with ChatGPT or Claude, or use Zapier's own AI builder.

Pro tip — ringless voicemail: through HighLevel you can drop a pre-recorded MP3 straight into a prospect's voicemail (no call). Keep it generic — no "Hi [name]" — but reference the specific meeting they missed. A simple, surprisingly effective re-engagement play.

Legal note: be careful what you put into free AI

Jodi, an attorney in our working group, closed with a privacy caution worth repeating. Her summary: if you're involved in a dispute and you type the details into a free AI tool — asking "how much trouble am I in?" or "do I need a lawyer?" — that history may be discoverable, much like a search history. The headline takeaway: with free AI tools, treat your inputs as if there's no expectation of privacy.

Important caveats she stressed: this is not settled law. Open questions remain about personal paid subscriptions versus enterprise systems, and about whether things like AI "memory"/skills could become discoverable. Expect a few years before it's clarified. The practical guardrails the group endorsed: pay for your tools, turn on the strongest privacy settings, hand AI only the selective files it needs (not your entire drive), redact sensitive data, prompt it to fact-check and not fabricate, and assume anything you input could surface elsewhere.

This reflects Jodi's summary to the group and the working group's discussion, not formal legal advice. The area is evolving — recent rulings have addressed the discoverability of AI chat logs (see, e.g., coverage via the National Law Review). Verify current law with your own counsel.

Resources

The full, categorized automation library Kaitlyn's team runs is on the site as the Automation Playbook — every idea paired with a plain-English build blueprint. You can also browse the CRE Prompt Library and help shape future sessions through the member survey.

Recurring logistics: 3rd Friday of every month, 10:00 AM ET. Email Ivy at imarguerite@eyeqmonitoring.com · Register · Join the meeting.