How to automate competitor monitoring with AI
Every Monday at 7am: four competitors, five sources each, one line per change in Slack with a link and why it matters. On a quiet week it says “no changes”.
Four competitors swept every Monday, diffed against a dated baseline, posted as one line per change. That is the standing watch these four prompts build.
The manual version is a bookmarks folder opened in a panic before board meetings. The sources are public and the loop repeats identically, so it belongs on a schedule. This runs in Strawberry, where routines do browser work on a cadence and a companion carries the memory between runs.
| Manual check-ins | A Strawberry routine | |
|---|---|---|
| When it happens | Before board meetings, in a panic | Every Monday at 7am, unattended |
| Coverage | Whatever tabs you remember | Same five sources per competitor, every run |
| Change detection | “Didn’t this page look different?” | Diffed against a dated baseline |
| Where it lands | Someone’s memory | Notion pages plus a one-line-per-change Slack digest |
| Cost of a quiet week | An hour to confirm nothing happened | One line: “no changes” |
What counts as a change?
Monitoring does not fail by missing things.
It fails as a noisy digest nobody reads by week three. So tell your companion what matters, once, in a message it remembers.
Prompt: “You’re going to track four competitors for me: Acme, Northwind, Coyote, and Initech. I care about exactly five things: pricing or packaging changes, new product announcements or changelog entries, senior hires and any open GTM roles, new case studies or named customers, and G2 review themes. Everything else is noise. Don’t report it.”
Take the baseline snapshot
A watch needs a before.
Have the companion sweep everything once and file it where your team can see it, in Notion or a doc.
Prompt: “For each of the four, go through their pricing page, changelog or release notes, blog, careers page, and their G2 reviews from the last 90 days. Build a baseline page per competitor in my Notion under ‘Competitive’, with a screenshot of each pricing page and the date. Note anything that contradicts our positioning doc. It’s the tab I have open.”
That last line is worth copying. A companion reads the tabs you already have open, so “compare it to this” is a sentence rather than an upload.
Put the sweep on a schedule
Now the part a person never sustains.
A routine re-runs the sweep and reports only what moved against the baseline.
Prompt: “Every Monday at 7am, re-check all of those sources. Compare against the baseline pages and update them. Then post a digest in the #competitive Slack channel: one line per change, with a link and why it matters, grouped by competitor. If nothing changed, say ‘no changes’ in one line. Don’t pad it.”
“Don’t pad it” is doing real work in that prompt. A one-line “no changes” is what keeps the channel trusted.
When should a deep dive kick in?
Most weeks the digest is enough. When a competitor rebuilds their pricing, you want depth the same afternoon.
Prompt: “Northwind just rebuilt their pricing page. Do a full teardown: what changed tier by tier, what they’re clearly optimizing for, which of our deals it affects, and what our reps should say when it comes up. Check the last 30 days of their reviews for early customer reaction. Give it to me as one page I can forward.”
That is ordinary research work for a companion: many tabs read in parallel, written up with a point of view.
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