💡 THE TIP

Never let a prospect end a call with “I’ll get back to you.”

Instead: “Totally fair. Do you want to A) put 15 minutes on the calendar to talk it through, or B) call this a no for now?”

Not booking the follow-up during the call is one of the fastest ways to lose a deal, because you lose your prospect’s attention.

Many founders are afraid to hear “this is a no for now” - but it’s actually much better to disqualify quickly and move on from a deal that is not a good fit.

Special shoutout to Chris Pisarski from Crustdata for this tip! Check out his tweet on it here.

✅ THE TO-DO

Listen to your last 5 sales calls. Count how many ended with “I’ll get back to you” without a next meeting booked. That number is your leak rate. If it’s more than 1 out of 5, make the binary close mandatory in your call framework.

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🤖 THE CLAUDE SKILL

Paste a call transcript or your notes and let Claude find the leaks.

Here's a transcript (or notes) from a recent sales call:

[PASTE TRANSCRIPT OR NOTES]

Find every "open loop" — moments where the prospect deferred a decision without 
committing to a next step. For each one:

1. Quote or paraphrase the moment
2. What the prospect was really saying (stalling, needs buy-in, genuinely unsure, 
   polite no)
3. The exact words I could have used to convert it into a binary close — natural 
   sounding, not scripted
4. If they raised an objection, how to address it AND land on a binary close in 
   the same breath

Also flag any buying signals I missed — something they said that showed interest 
but I didn't capitalize on.

Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.

💡 THE TIP

One founder we know sends every churned customer a $50 Amex gift card and a handwritten note asking for 15 minutes of honest feedback. The gift is unconditional (they keep it regardless), but the gesture gets 68% of churned customers to agree to a call.

The insight here is subtle. Churned customers have already decided to leave, which means they have zero incentive to sugarcoat anything. But most companies never ask, or they send a survey that gets ignored. The gift card and handwritten note signal that you genuinely want to hear the hard truth.

Special shoutout to Todd Saunders from Broadlume for this tip! Check out his tweet on it here.

✅ THE TO-DO

Pull your list of customers who churned in the last 90 days. Pick five. Write each a short, handwritten note (three sentences max) thanking them for being a customer and asking for 15 minutes of honest feedback. Include a $50 gift card. Don’t pitch them on coming back. Just listen. Track what you hear and look for patterns after all five calls.

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🤖 THE CLAUDE SKILL

Paste this into Claude to draft the outreach note, a discussion guide for the call, and a framework for synthesizing what you learn.

You are a customer success strategist. I run [COMPANY NAME], which sells [PRODUCT DESCRIPTION] to [TARGET CUSTOMER]. We recently lost [NUMBER] customers over the past [TIME PERIOD].

I want to send each churned customer a handwritten note with a $50 gift card asking for 15 minutes of feedback. Please generate:

1. A short, handwritten-style note (3-4 sentences max). Warm, genuine, zero sales pitch. The gift card is unconditional. I just want their honest perspective.

2. A 15-minute discussion guide with 5 open-ended questions designed to surface:
   - The real reason they left (not the official reason)
   - What they switched to (if anything) and why
   - What would have changed their mind
   - What they'd tell a friend about the product

3. A simple synthesis template I can fill in after each call to track patterns across churned customers (a table with columns for: customer name, stated reason, real reason, switched to, what would have saved them, biggest surprise from the call)

Tone: curious and humble, not defensive. I want them to feel safe being blunt.

Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.

💡 THE TIP

Staple a one-page plain-English summary to the front of every contract you send.

Every enterprise deal stalls in the same place: the customer’s lawyer gets the MSA, sees 30 pages of dense prose, and the deal disappears into the legal queue for two weeks. But here’s the thing: that lawyer is looking for the same 10 things every other lawyer looks for. Liability cap, payment terms, IP, data, and termination, among other things. The list barely changes from deal to deal.

So answer the questions before they’re asked. A one-pager at the front of the contract that’s written in plain English, readable by your AE, your champion, and their GC, collapses the review cycle. Your salespeople can talk through it on the call. Your champion can forward it to legal with confidence. And legal can scan it in 90 seconds instead of 90 minutes.

More than simply being a legal document, it’s a translation layer. Same answers, surfaced upfront.

✅ THE TO-DO

List the 10 questions a buyer’s lawyer asks every time (liability cap, indemnification, payment terms, term & renewal, IP, data rights, security, termination, SLAs, governing law). For each, write the answer from your standard MSA in one plain-English sentence with a section reference. That’s your template. Attach it to every contract you send going forward.

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🤖 THE CLAUDE SKILL

Paste this into Claude with your contract and let it generate the one-pager for you.

You're helping me accelerate legal review on an enterprise contract. I'm going to give you a contract, and I want you to generate a one-page plain-English summary that I'll staple to the front of the document before sending it to the customer.

The audience is three people reading the same page: my AE, my customer champion, and the customer's lawyer. It needs to be readable by all three.

CONTRACT:
[PASTE CONTRACT OR ATTACH FILE]

DEAL CONTEXT (optional):
- Counterparty: [COMPANY NAME]
- ACV: [DOLLAR AMOUNT]
- Contract type: [MSA / order form / DPA / etc.]

Produce a markdown table answering the 10 questions every buyer's lawyer asks. Skip rows that genuinely don't apply.

| Question | Answer (plain English) | Section |
|---|---|---|
| How long is the term and how does it renew? | | |
| What are the payment terms? | | |
| What's the liability cap? | | |
| Who indemnifies whom, and for what? | | |
| Who owns the IP? | | |
| What are the data rights and security commitments? | | |
| How can either party terminate? | | |
| What are the SLAs and remedies if we miss them? | | |
| What's the governing law and dispute process? | | |
| Anything unusual or non-standard? | | |

Rules:
- Translate, don't paraphrase. "Indemnify and hold harmless" becomes "we pay their legal costs if a third party sues them because of our software."
- Use numbers wherever possible: dollars, days, percentages.
- Below the table, add a "⚠️ Watch-outs" section flagging anything aggressive, non-standard, or likely to trigger redlines.
- If a term is silent in the contract, say "Not addressed" — don't infer.

Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.

💡 THE TIP

When a prospect says “we need [feature] before we can sign,” don’t let that kill the deal. Instead, flip it: “If I showed you we finished that by Friday, would you be ready to sign today, or is something else holding us back?”

This question does two things at once. First, it surfaces whether the feature is the real blocker or just a convenient stall. If they say “well, actually there’s also the budget question,” you’ve just uncovered the real objection. Second, if the feature genuinely is the last thing, you can sign the contract with delivery contingent on completion. You’ve turned a stall into a commitment with a clear engineering deadline.

Special shoutout to Chris Pisarski from Crustdata for this tip! Check out his tweet on it here.

✅ THE TO-DO

Look at your current pipeline and find one deal that’s stalled on a feature request. Before your next call with that prospect, write down the exact question: “If we delivered [FEATURE] by [DATE], would you be ready to sign, or is there something else?” Ask it on the call. Whatever they say, you’ve moved the deal forward, because now you know what’s actually in the way.

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🤖 THE CLAUDE SKILL

Paste this into Claude with a stalled deal to generate a talk track, contingent contract language, and a framework for separating real objections from convenient stalls.

You are an enterprise sales coach. I have a deal that's stalled because the prospect says they need a feature we haven't built yet. Here are the details:

- Prospect company: [COMPANY]
- Buyer persona / title: [TITLE]
- Product they're evaluating: [YOUR PRODUCT]
- Feature they're requesting: [FEATURE]
- How far along the deal is: [STAGE, e.g., "verbal yes pending this feature"]
- Approximate deal size: [ACV]

Please generate:

1. A talk track (3-4 sentences) for the "if we built this by X, would you sign today?" conversation. It should feel consultative, not aggressive.

2. Two follow-up questions depending on their response:
   a. If they say "yes, that's the only thing" (how to lock in the commitment)
   b. If they say "well, there's also..." (how to unpack the real objection)

3. A short contingent clause I could propose adding to the contract: delivery of [FEATURE] by [DATE], with a defined acceptance criteria, and what happens if we miss the deadline (e.g., 30-day opt-out window).

4. A quick gut-check: based on the deal details, does this feel like a real feature blocker or a polite stall? What signals should I look for?

Tone: direct, strategic, empathetic. I want to close this deal without being pushy.

Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.

💡 THE TIP

Your support queue is a hidden marketing channel. After your team resolves a ticket and the customer replies with a “thank you,” that’s a moment of peak goodwill. The customer just had a problem solved. They feel helped. Use that moment to share something valuable: a webinar invite, an upcoming event, a new feature announcement.

This isn’t about being salesy…it’s about offering a consultative value add. Rarely will you find an opportunity to help a customer at exactly the moment they’re most receptive to it, but support tickets are one of them. A well-timed “Hey just in case it’s helpful - we are hosting a [workshop/dinner/webinar] on [this very topic] on [date]. If you'd like to dive in deeper, it should be a useful session!” converts better than almost any cold outreach, because the trust is already warm.

✅ THE TO-DO

Work with your support team to create one templated follow-up line they can append after resolving a ticket. Keep it short and relevant: “Glad we could help! By the way, we have [EVENT/RESOURCE] coming up on [DATE] that you might find useful if you'd like a deep dive: [LINK].” Update it monthly with whatever your current marketing priority is. Measure click-through rates on the links to see what resonates.

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🤖 THE CLAUDE SKILL

Paste this into Claude to generate a library of post-resolution follow-up messages your support team can rotate through.

You are a customer marketing strategist for a B2B software company. Our product is [PRODUCT NAME / ONE-SENTENCE DESCRIPTION]. Our support team resolves tickets and often gets positive "thank you" replies from customers.

I want to use these moments of goodwill to share relevant marketing content. Please generate 5 short follow-up snippets (2-3 sentences each) that a support rep can append after a resolved ticket. Each should:

- Feel natural and human, not templated or salesy
- Reference a different type of content: [LIST YOUR CONTENT TYPES, e.g., webinar, customer event, new feature launch, case study, community Slack]
- Include a [PLACEHOLDER] where the rep inserts the specific link or date
- Match the tone of a helpful colleague, not a marketing email

Also suggest 2 rules of thumb for when NOT to use these (e.g., if the ticket was a major outage, if the customer expressed frustration).

Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.

💡 THE TIP

Flip your proof-of-concept model from opt-in to opt-out. Instead of running a free trial and hoping the prospect converts, get the full agreement signed upfront with a 90-day free period that auto-converts to paid on day 91.

The difference is enormous. Opt-in POCs attract tire-kickers. Opt-out POCs filter for serious buyers, because a prospect who won’t do the procurement work upfront is telling you something: they’re not ready to buy. You haven’t lost a deal; you’ve saved yourself 90 days of false pipeline. The auto-conversion also shifts the default from “convince me to stay” to “convince me to leave,” which is a much better position to sell from.

✅ THE TO-DO

Take your current POC or pilot agreement and rewrite the structure: full contract signed on day one, 90-day evaluation window, automatic conversion to paid unless the customer explicitly opts out. Run it past legal this week and test it on your next qualified opportunity. Track whether your POC-to-paid conversion rate changes over the next quarter.

If you found this tip helpful, please share with a fellow b2b founder 😎

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🤖 THE CLAUDE SKILL

Paste this into Claude to draft opt-out POC contract language and a talk track for positioning it with prospects.

You are an enterprise sales strategist. I sell [PRODUCT] at an ACV of approximately [ACV RANGE] to [BUYER PERSONA] at [COMPANY SIZE] companies.

Currently we run a standard [CURRENT POC LENGTH]-day proof of concept that converts to paid if the customer opts in. I want to switch to an opt-out model: full agreement signed upfront, [DESIRED FREE PERIOD]-day free evaluation period, auto-converts to paid on day [DESIRED FREE PERIOD + 1].

Please generate:

1. A one-paragraph summary of the opt-out POC structure I can share with my legal team
2. A talk track (3-4 sentences) for explaining this model to a prospect in a way that frames it as a benefit to them (less risk, faster time to value, no second procurement cycle)
3. Two common objections a prospect might raise about signing upfront, with suggested responses
4. Success criteria I should define with the customer during the evaluation period so there's a clear "did this work?" conversation before day [DESIRED FREE PERIOD]

Tone should be consultative, not pushy. The goal is to make the prospect feel like this structure respects their time.

Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.

💡 THE TIP

Run a webinar that’s just an overview of your company and a live product demo. No guest panel. No thought leadership angle. Just “here’s who we are and here’s what we built.”

Most companies skip this because it feels too basic. But your prospects are drowning in content and starving for clarity. A founder a company we know ran a monthly “Product 101” webinar and it became their highest-converting top-of-funnel channel, beating every ebook and sponsored post. The people who show up are self-selecting as genuinely curious. That’s the best lead quality you can get.

✅ THE TO-DO

Pick a date in the next two weeks and schedule a 30-minute webinar with a dead-simple title: “[Company Name]: What We Do and How It Works.” No panel, no co-marketing partner, no fancy theme. Promote it to your existing email list and one social channel. Run it, see who shows up, and follow up with every attendee within 24 hours.

🤖 THE CLAUDE SKILL

Paste a call transcript or your notes and let Claude find the leads.

You are a B2B marketing strategist. I'm running a simple "Company Overview + Product Demo" webinar for [COMPANY NAME]. We sell [ONE-SENTENCE PRODUCT DESCRIPTION] to [TARGET BUYER PERSONA].

Please generate:

1. A webinar title that is clear and literal (no clever wordplay)
2. A 30-minute agenda broken into timed segments (intro, company context, live demo, Q&A)
3. Three short promotional blurbs I can use:
   - One for email (50 words max)
   - One for LinkedIn (40 words max)
   - One for a Slack community post (30 words max)
4. A follow-up email template for attendees (warm, personal, includes a CTA to book a call)

Keep everything direct and jargon-free. The tone should feel like a confident founder explaining their product to a smart friend, not a marketing team running a campaign.

Do you have a GTM protip? Send our way here to feature in an future issue!

💡 THE TIP

For all you founders in conference szn (RSA and KubeCon 👀), this one’s for you: send your follow-up emails the same night you meet someone at a conference. From your hotel room and before you go out.

This is an underrated source of competitive edge. While you’re sending a personalized note at 7 PM, every other vendor is at the happy hour planning to “follow up next week.” By the time their generic batch email lands five days later, yours is already read.

One founder we work with made this mandatory: no one leaves until follow-ups are sent. Response rates nearly doubled. Same leads, same product, same team. Just a different 45 minutes.

✅ THE TO-DO

Before your next conference, create a follow-up template in your drafts: a skeleton with blanks for [name], [what we discussed], and [next step]. This is the scaffolding that lets you write 15 personalized emails in 30 minutes instead of staring at a blank screen. Build it before the conference. Fill it in that night.

🤖 THE CLAUDE SKILL

Paste a call transcript or your notes and let Claude find the leads.

I just got back from [CONFERENCE NAME]. I need to send personalized follow-up 
emails to everyone I met today. For each person, write a short email (3-5 sentences) 
that:

- Opens with something specific from our conversation (not “great to meet you”)
- Connects what we discussed to one clear next step
- Sounds like a real human wrote it at 7pm after a long day — warm, not overly polished
- Ends with a specific ask (15-min call, intro, sharing a resource)

My company: [ONE SENTENCE — what you do]

People I met:
1. [Name, company, role] — Talked about [topic]. They mentioned [pain point]. 
   Next step: [what you’d want to do next]
2. [Name, company, role] — Talked about [topic]. They mentioned [detail]. 
   Next step: [next step]
3. [repeat for each person]

Write each email with a subject line. Keep them short — these people are also 
exhausted from the conference.

Do you have a GTM protip? We’d love to feature you! Send our way here for a future issue!