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If you've been meaning to try AI in your sales workflow but haven't found the right place to start, this issue is for you. Today we're giving you a single prompt you can paste into ChatGPT or Claude right now to practice handling objections before your next call. No setup. No new tools. Just open a tab and go. Plus: a real experiment where AI agents negotiated 186 deals (and why timing beats everything), a tool that coaches your cold emails in real time, and five quick wins you can use today.
THE PLAY
5 Pipeline Audits You Can Run with AI Before Monday's Standup
Most reps check their pipeline the same way every week: scroll through their CRM, eyeball the close dates, and tell their manager everything looks fine. Then deals slip. Then the forecast misses. Then everyone scrambles.
Here’s a better way to do it. Copy your pipeline into ChatGPT (or Claude), ask it five specific questions, and get back a clear picture of which deals are solid and which ones are about to stall. It takes about five minutes. You will know more about your pipeline after this exercise than most reps know after an hour of CRM clicking.
How to set it up (2 minutes):
Step 1: Open your CRM. Pull up your open deals closing in the next 30 to 60 days. You need: deal name, deal size, close date, current stage, and last activity date. If your CRM has an export button, use it. If not, just copy and paste the list into a ChatGPT or Claude window (OR if your CRM connects to Claude I’d just connect it and them prompt inside of Claude. Way easier).
Step 2: Paste the prompt below into the same window, right after your pipeline data.
The Prompt (copy and paste this after your pipeline data):
I just pasted my sales pipeline above. These are my open deals. Run five audits and give me the results in a simple table for each one.
Audit 1: Stale Deals
Flag any deal where the last activity was more than 14 days ago. Label it "at risk" and tell me what to do first (email, call, or walk away).
Audit 2: Close Date Reality Check
Flag any deal where the close date is within 14 days but the stage suggests it is not close to done (e.g. still in "discovery" or "proposal sent" with no recent follow-up). Suggest a realistic new close date.
Audit 3: Pipeline Concentration Risk
Tell me what percentage of my total pipeline value is sitting in my top 3 deals. If it is above 50%, flag it and tell me why that is a problem.
Audit 4: Stage Bottleneck
Count how many deals are in each stage. If more than 40% are stuck in one stage, flag it and suggest one action to get them moving.
Audit 5: The "Be Honest" Check
Based on the data, pick the 3 deals most likely to slip or lose. For each one, give me a one-sentence reason why and one thing I can do this week to save it.
After all five audits, give me a one-paragraph summary: how healthy is this pipeline, what is the biggest risk, and what is the single most important thing I should do Monday morning?What you’ll get back:
Five tables, one per audit. Each one flags specific deals and tells you exactly what to do. No guessing, no generic advice.
Audit 1 example (Stale Deals):
❌ What most reps do: Leave the deal in the pipeline because "they said they were interested three weeks ago."
✅ What the audit tells you: "Acme Corp: last activity 22 days ago, still in Discovery stage, $45K deal. At risk. Action: send a direct check-in email today. If no response in 48 hours, move to Lost."
Audit 3 example (Concentration Risk):
❌ What most reps do: Feel great because the pipeline total looks big.
✅ What the audit tells you: "67% of your pipeline value is in 3 deals. If any one of them slips, your quarter is in trouble. You need more at-bats in early stages to reduce concentration risk."
Audit 5 example (The "Be Honest" Check):
❌ What most reps do: Tell their manager "I feel good about this one."
✅ What the audit tells you: "NovaTech: close date is May 23 but only one stakeholder involved, no budget confirmation, and last email went unanswered. This deal is likely to slip. Action: request a meeting with the economic buyer this week or push the close date to June."
💡 Pro Tip: Run this every Sunday night or Monday morning before your team standup. When your manager asks "how's the pipeline looking?" you’ll have specific answers instead of feelings. After a few weeks, you’ll start spotting the patterns yourself: which deals go stale, where your bottleneck lives, and how concentrated your pipeline really is. |
Try this today. Export your pipeline or connect your CRM, paste the prompt, and read what comes back. Five minutes and you will know exactly which deals need attention this week.
IN PARTNERSHIP WITH VIKTOR
We hired one colleague for every department.
Last Tuesday, marketing asked Viktor to write the weekly campaign recap, pull performance from Google Ads and Meta, and format it as a PDF for the exec team. Done in four minutes.
That same afternoon, engineering asked Viktor to review three open pull requests on GitHub, cross-reference with the Linear sprint board, and flag anything blocking the release. Posted to private channel before standup.
At 9pm, ops asked Viktor to draft a vendor contract summary from three Notion docs and send it to the team. It was in #ops by morning.
None of them knew the others were using it.
Same colleague. Three departments. That's what changes when your AI coworker lives in Slack, where your whole company already works. It's not a tool one person logs into. It's a teammate everyone messages.
5,700+ teams. SOC 2 certified. Your data never trains models.
"Viktor is now an integral team member, and after weeks of use we still feel we haven't uncovered the full potential." - Patrick O'Doherty, Director, Yarra Web
THE SIGNAL
Gong Just Hit $500M in Revenue. Here’s What That Means for Every Sales Rep.
Gong announced last week that it surpassed $500 million in annual recurring revenue, growing 55% year over year. That is the tenth straight quarter of accelerating growth. Half of the Fortune 10 now uses the platform, and they added more $1M+ enterprise deals in the last two quarters than in the prior six combined.
Here’s the part that matters for individual reps: companies are not just buying Gong to record calls anymore. They are consolidating their entire revenue stack onto AI platforms. Gong Forecast, Gong Engage, Gong Enable. Enterprises are replacing four or five point solutions with one system that watches every deal, scores every interaction, and flags risk before humans notice it.
The numbers from their customers are real. Anthropic increased sales productivity by 64% and saved reps roughly 10 hours per week using Gong. Uber for Business improved response rates by 32%. Canva increased salesperson productivity by 60%.
🎯 What this means for you: Your company is either already using AI to analyze your pipeline and calls, or they will be soon. The reps who will thrive are the ones who are already comfortable working alongside AI: using it to prep for calls, audit their pipeline, and spot patterns in their conversations. That is exactly what The Play above helps you practice. Start building the habit now, because the tools are coming whether you are ready or not. |
THE STACK SWAP
Monaco: The All-in-One Sales Platform Built Around Timing, Not Volume
Most sales tools help you find people to contact. Monaco helps you figure out who to contact right now and why this week instead of last week.I've personally been using the platform for about a month and going to share my thoughts and feedback:
What it does: Monaco is an AI-native sales platform that builds your total addressable market automatically, layers intent signals on top (job postings, tech stack changes, funding rounds, hiring patterns), and tells you which accounts to prioritize based on timing. It also runs outbound sequences, records meetings, manages your pipeline, and replaces your CRM. Everything lives in one system. We needed this as a team badly since our CRM, LI and outbound platform were all disconnected.
What it replaces: The combination of a CRM (HubSpot or Salesforce), a prospecting database (ZoomInfo or Apollo), and a sequencing tool (Outreach or Salesloft). Monaco bundles all three into a single subscription with AI that actually maintains the data for you.
Who it's for: Early-stage startups (seed to Series A) that need a sales engine but do not want to stitch together five different tools and hire an ops person to maintain them. If you are a founder or early sales hire building outbound from scratch, this is worth a look. Our team is small and has gotten a lot of value from it already
Why it matters: The biggest differentiator is the signal layer. Instead of blasting your whole TAM and hoping someone bites, Monaco overlays custom intent signals so you are reaching out when accounts are showing real buying behavior. It is the difference between "this company fits our ICP" and "this company fits our ICP and just posted three job listings that match our use case." Timing is the edge.
What to know before you try it:
Monaco launched in February 2026 and is still in public beta. Pricing is a flat fee (not per seat) but the exact number is not published. You will need to book a demo.
It does not include a phone dialer or website visitor identification. If those are core to your motion, you will need separate tools.
The standout feature beyond the software: Monaco embeds a "forward deployed AE" with your team. An experienced salesperson who monitors the AI, guides strategy, and handles customer meetings alongside you.
I can confirm it does include some LinkedIn automation, like sending requests and messages if they accept a connection request. Outside of that, I don't think it has other LinkedIn automations.
Founded by former Founders Fund partner Sam Blond. Backed by $35M from Founders Fund, the Stripe founders, and Y Combinator president Garry Tan.
PS - I should really get a tool to sponsor this section lol. So far, these have all been unsponsored.
QUICK WINS
1. After you run The Play above, ask one follow-up question: "Based on this pipeline, what is my realistic close rate for this month? Give me a percentage and explain your reasoning." It forces a hard number instead of a feeling. Most reps overestimate by 20 to 30 percent.
2. If you are between roles or know someone who is: Find a Sales Job in 30 Days. One of the best playbooks we have seen for getting back on your feet fast.
3. Before your next deal review, paste the prospect's last three emails to you into ChatGPT and ask: "Is this buyer engaged, stalling, or ghosting? What should I do next?" You will get a straight answer in 10 seconds.
❌ "I think they are still interested."
✅ "Their response time went from 2 hours to 6 days. They are stalling. Send a direct check-in with a specific next step."
4. A quick gut check for your pipeline: you should have 3x your quota in open pipeline at any given time. If you are below that, the problem is not closing. The problem is prospecting. Open ChatGPT, paste your target list, and ask: "Which 10 of these companies are most likely in a buying cycle right now based on recent hiring, funding, or expansion activity?" Use those 10 as your priority outbound list this week.
THE CLOSER
Next week in Sales Bytes: we’re doing a deep dive on one tool that can change how you prospect, sell, or close. If there is a tool you want us to break down, reply to this email.
Know a sales leader running Monday pipeline reviews? Forward them this issue. That pipeline audit prompt alone is worth the read.
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FREE RESOURCES
To start getting immediate value from AI I've built the library (and will continue to build more) for top AI sales tools, prompts, tricks, and tips.
