Start here · Week one
Start here: your first week with AI for sales
You don't need a budget or a plan. You need one real task from your week and one free AI chat tool (ChatGPT, Claude, Gemini, or Grok can run these plays; our own runs so far were in one tool, so results in yours may differ; free tiers have usage limits that change).
Do these three things first
- Use fake or public info while you learn. Don't paste customer data into a free AI tool until you've read your company's policy and the tool's privacy settings.
- Read the draft out loud before you send it. If it doesn't sound like you, rewrite it.
- Pick one play per day. Not all three at once. Keep notes: how long it took, what you changed. That's your own measure of whether it helps.
Your path
Pick your role
SDR / BDR: week-1 path
- Day 1: Make a 10-minute account research brief from a company's own website text — Paste a company's own website text into an AI chat tool and get a short brief. Check it against the page.
- Day 2: Write 5 different cold-email angles under 75 words for one persona — Have the AI draft five angles, then you pick one and rewrite it in your voice.
- Day 3: Draft a LinkedIn connect note plus two follow-up messages, with no fake flattery — The AI drafts, you copy it over and send it by hand.
Account Executive: week-1 path
Account Manager / CSM: week-1 path
Renewal-specific plays are coming; these three apply today.
- Day 1: Shorten and fix a weak email, with a list of what changed and what to double-check
- Day 2: Build a 5-minute pre-call brief: goal, hypotheses, questions, and unknowns — Use your customer's account notes.
- Day 3: Write a 3-touch follow-up sequence for a lead that went quiet, each touch a different angle
Sales Manager: week-1 path
Coaching and forecast plays are coming.
- Day 1: Diagnose a stalled deal and get a ranked 14-day action plan — Give the AI your deal notes and get a ranked action plan to bring to your next one-on-one.
- Day 2: Turn your top 5 objections into a spoken reply, an email reply, and a question back — Feed the AI your team's real objections and build one shared cheat sheet, edited by your reps.
- Day 3: Build a discovery question bank for one persona, with cost-of-inaction probes — Have the AI build a question bank, then compare it to what your reps actually ask.
Owner who sells: week-1 path
- Day 1: Write quote follow-ups for day 1, day 3, and day 7, each ready for you to approve — Paste in the facts of an open quote and get day 1, 3, and 7 drafts. Start with the quotes sitting unanswered right now.
- Day 2: Write a 3-touch follow-up sequence for a lead that went quiet, each touch a different angle
- Day 3: Shorten and fix a weak email, with a list of what changed and what to double-check
How we label plays
Selling With SI is mainly a site of ideas and examples for salespeople to try. Every play is checked for safety and quality before it goes up, and every play carries one label that says how much evidence is behind it. A label is not a promise of results.
- Used in real prospecting
The author has used a version of the play in real prospecting. What happened is self-reported: we show it as the author's own account, not as a measurement. Where the author's version differed from the play on the page, the play page says so.
- Tried in an AI tool
We ran the play ourselves, with fictional inputs, in the AI tool and the number of runs the badge and the play page state. Runs in one tool say little about other tools, and results vary by tool, model, and input.
- Idea: not tried yet
We have not run it. It is an idea worth trying, with steps and a prompt, and nothing on the page shows that it works.
- We don't say "tested" loosely. We use that word only if a play has at least 3 logged runs in at least 2 different AI tools. No play here meets that bar yet.
- No made-up proof. No invented statistics, reviews, or testimonials. Time saved is shown only when we measured it; otherwise it says "Not measured yet."
- You stay in charge. Every play ends with a person checking the draft before anything is sent. Read Safe Use before you contact a real person.
After week one
- Keep the AI plays that saved you time. Drop the rest. That's normal.
- Want more? Get new AI plays by email (signup is a placeholder for now).
Newsletter · Free
AI and SI plays for sales, by email
New plays as they pass our safety and quality review, plus one AI tool to try and one thing not to automate.