💡 THE TIP

Stop re-engaging closed-lost deals on a nine-month timer. Instead go when the door actually reopens.

Most teams treat closed-lost like a snooze button: nine months pass, a rep sends a generic “checking back in” note. That’s a guess, not a signal.

Per Kyle Poyar and Brendan Short, the real trigger is a signal cluster: a new VP, a funding round, the champion who killed your deal leaving the company. When two or three land together, the follow-up names the actual reason the deal died (a feature gap, a reorg that pulled budget), not a vague check-in.

Check out Kyle Poyar’s piece, The best AI-native GTM plays you’re not running for more.

✅ THE TO-DO

Pull your closed-lost list from the last 12 months. For each deal, write down the specific objection that killed it — not the CRM's generic "no budget" tag — and pick one signal (champion job change, funding round, new leadership hire) that would tell you it's worth trying again.

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

Share

🤖 THE CLAUDE SKILL

Paste this into Claude with your last call transcript from the deal and whatever new signal just came in.

You are helping me re-engage a closed-lost deal. Here is context:

- Account: [ACCOUNT NAME]
- Deal closed-lost on: [DATE]
- Last call transcript or notes: [PASTE TRANSCRIPT/NOTES]
- New signal that just happened: [E.G. NEW VP HIRED, FUNDING ROUND, CHAMPION LEFT/PROMOTED]
- What we sell / the specific use case: [PRODUCT + USE CASE]

Do the following:
1. Read the transcript/notes and identify the ONE specific objection or reason
   the deal actually died — not a generic label like "no budget."
2. Explain in one sentence why the new signal changes that objection (e.g.,
   new budget owner, prior blocker gone, bigger buying power now).
3. Draft a short re-engagement email (under 120 words) that:
   - References the real reason the deal stalled, briefly and without blame
   - Names the new signal naturally, not like a stalking confession
   - Makes a low-friction ask (15 minutes, not "let's re-scope the whole deal")
4. Give me two subject line options: one direct, one curiosity-driven.

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

The best demo question is not "any questions?" It is "if this were yours, what would you do with it?"

When Nick Cegelski runs demo calls, there is one question he’s found to improve prospect engagement. Instead of narrating through a screen and stopping to ask “any questions?”, he asks prospects to hold the product: “If you were looking at this dashboard, which KPIs would you drill into first?” or “Where would you integrate this into new hire onboarding?” or “What data here would you want to show your COO?”

The question does two things. It gets the prospect to picture life after they sign, and it surfaces real signal about how they would actually use the product. That is more useful than anything “any questions?” would ever uncover.

Special shoutout to Nick Cegelski for this tip! Read his full post here.

✅ THE TO-DO

Before your next demo, pick one screen and write a “hold” question for it specifically. Not “any questions?” but something like “if you were running this report, what would you be looking for?” Use it once and watch how the conversation shifts.

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

Share

🤖 THE CLAUDE SKILL

Paste this into Claude before your next demo to generate a full set of “hold” questions for every screen you plan to show.

You are a sales coach helping me prepare demo questions that get prospects
to envision using my product.

My product: [ONE OR TWO SENTENCES ON WHAT IT DOES]
My typical buyer: [ROLE, COMPANY SIZE, INDUSTRY]
Screens or features I plan to show in my next demo: [LIST 3-5]

For each screen or feature I listed, write one "hold" question I can ask
the prospect mid-demo. Each question should:
1. Invite them to imagine they already own the product
2. Be specific to that screen or feature, not generic
3. Surface how they would use it in their actual workflow

Format: [Screen / Feature]: [Question]

Then give me one fallback "hold" question I can use on any screen if I
go blank mid-demo.

📰 For Your Additional Reading

Last week we published our Work-Bench AI Snapshot report covering the biggest developments in tech and AI over the first half of the year. Visit our blog post here to download the full report and join us July 1 at 1pm ET for our webinar — signup here.

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

An underrated way to close more is to write down who shouldn’t buy from you.

When launching a new product Amanda Zhu, Co-Founder at Recall.ai, defined three things a customer had to need to be a good fit to buy. If they didn’t hit at least two, the team walked. The doc gave the sales team permission to say no — and stopped reps from burning time on deals that were never going to close.

Most sales teams are implicitly disqualifying already — the experienced reps know who to walk from. Writing it down turns that instinct into a repeatable process instead of tribal knowledge only some people have.

Special shoutout to Amanda Zhu from Recall.ai for this tip! Read her full post here.

✅ THE TO-DO

Pull your last 10 lost deals and find the pattern. What did the bad-fit customers have in common? Write it down as a “do not sell to” list — with the reason next to each one. Then define the 3 things a customer has to need for your product to be a fit. Share it with your team before your next pipeline review.

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

Share

🤖 THE CLAUDE SKILL

You want to build a disqualification doc your sales team will actually use. Paste this into Claude:

You are a GTM strategist helping a B2B sales team define who they should NOT sell to.

My context:
- What my product does: [ONE OR TWO SENTENCES]
- Our current ICP (who we think we're selling to): [DESCRIBE]
- Recent lost deals or bad-fit customers we've encountered: [LIST ANY EXAMPLES]
- What our product does best / our biggest differentiator: [DESCRIBE]

Help me build a "do not sell to" doc with the following sections:
1. Red flags: specific signals that indicate a prospect is not a fit, with a brief explanation of why for each
2. The 3 things a customer must need for us to be a genuine 10x solution (not just a nice-to-have)
3. The conversations reps should have to surface misfit early — specific questions to ask in discovery

Be direct. Write this as something a new sales rep could read in 5 minutes and know exactly who to walk away from.

📰 For Your Additional Reading

This week we published our Work-Bench AI Snapshot report covering the biggest developments in tech and AI over the first half of the year. Visit our blog post here to download the full report and join us July 1 at 1pm ET for our webinar — signup here.

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

Conference stunts are back — and the best ones don't require a booth, just someone paying attention.

When Zendesk held their annual Relate conference in Denver, Cassie Carter checked the weather forecast and saw rain coming. Pylon showed up with hundreds of purple umbrellas, a purple coffee truck parked directly across from the venue entrance, and purple video trucks circling the city all day.

No booth. No sponsorship fee. Just purple everywhere — in a city full of Zendesk’s customers.

And because they were there, they got to talk to those customers. What they learned was valuable intel: Zendesk’s AI isn’t working for B2B, companies still can’t reach customers over Slack and WhatsApp, and that a lot of attendees had already heard of Pylon.

Special shoutout to Marty Kausas, CEO of Pylon, for this tip! Check out his post on it here.

✅ THE TO-DO

Find your top competitor's next conference and put it on the calendar. A week before, assign someone to check what's happening in that city that week. What could you turn into a brand moment?

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

Share

🤖 THE CLAUDE SKILL

Your competitor’s event is coming up. Paste this into Claude to build your ambush plan.

You are a GTM strategist helping a B2B startup create a high-impact, low-cost marketing moment around a competitor's upcoming conference or user event.

My context:
- My company: [COMPANY NAME AND ONE-LINE DESCRIPTION]
- My competitor hosting the event: [COMPETITOR NAME]
- The event: [EVENT NAME, LOCATION, DATE, APPROXIMATE ATTENDANCE]
- My positioning vs. the competitor: [E.G. "We're the modern B2B-native alternative to their legacy product"]
- My budget for this: [BUDGET RANGE]
- My brand colors and personality: [E.G. "Purple, irreverent, challenger brand"]

Generate 5 specific ambush marketing concepts I could execute near or around this event. For each:
1. Name the tactic (e.g., "Competitor Dinner," "Coffee Truck," "Geo-targeted Ad Blitz")
2. What does it look like in execution? Be specific — what does someone physically see or experience?
3. Estimated cost range
4. Social/viral mechanic — why would an attendee photograph or share this?
5. Key risk or thing that could go wrong

Prioritize concepts that work with a small team, would make our competitor uncomfortable, and have a strong enough visual to earn organic sharing. Rank from lowest-effort/highest-leverage to highest-effort/highest-reward.

💡 THE TIP

Maximize every API at your disposal – especially the mundane ones nobody thinks of as a sales tool.

Clay’s enterprise GTM team turned a boys’ trip to the Masters into a 100x pipeline-to-spend campaign. Here’s how it ran.

They raided the merch store in Augusta, walked out with $3,000 in hats and mugs, then used Claygent to comb social profiles and surface the golf fans among their prospects at Tier 1 accounts – some buyers wrote about golf on LinkedIn; some played in college. Then they shipped the merch to those individuals.

Most teams would have stopped there.

Instead, Varun Anand’s team piped UPS’s package-tracking API into their systems, and the moment a box read “delivered,” they fired off an automated, personalized email as the gift landed in the prospect’s hands.

The insight here is subtle. We in tech think of Clay – but how many folks think of the UPS API? What are other feeds that are overlooked but can take your campaign from good to great?

Special shoutout to Varun Anand at Clay for this tip!

✅ THE TO-DO

List every tool that touches your customers: shipping, billing, calendars, support, product usage. Pick one with an API that reveals how customers behave but that nobody on your team treats as a sales signal. In Clay (or your tool of choice), pull in that data and build one trigger off it.

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

Share

🤖 THE CLAUDE SKILL

Paste this into Claude to mine your own stack for overlooked signals before you go build them in Clay.

Act as a GTM engineer. Help me find non-obvious data signals I could turn into
timely, automated outreach — the kind of "mundane" APIs my competitors ignore.

My context:
- What I sell, in one line: [PRODUCT]
- Who I sell to: [ICP — TITLES + COMPANY TYPE]
- What a real buying moment looks like for me: [E.G. "they just hired a VP Sales"]
- Tools/data I already touch: [E.G. SHIPPING, BILLING, CALENDARS, SUPPORT, USAGE]

Give me 8 overlooked data sources or APIs (think shipping/tracking, weather,
job boards, app-store reviews, tech-stack changes, permit filings, etc.) that
could signal intent or a perfect moment to reach out.

For each, output a table row with:
1. The API / data source
2. The signal it reveals
3. The exact trigger I'd wire up in Clay
4. A one-line message angle for the follow-up

Then rank them by signal strength vs. how easy they'd be to set up.

📺 For Your Additional View

Our Jessica Lin recently sat down with our Work-Bench CEO-in-Residence David Politis on his podcast, Not Another CEO.

For founders, Jess calls out two key points to hit in your Seed pitch in the first 5 minutes:

1. Demonstrating velocity - how have you and your team moved fast, shipped, learned, iterated with early customers and pipeline 🚀

2. Articulate a big, ambitious vision that will take you 10 years to achieve - right from the jump 💥

See more of Jess’ post here and why founders should focus less on their current ARR and growth rate to $2M ARR - but be crystal clear on how they have a plan to $800M+ in ARR in the next 10+ years for a venture-scale business.

🎙️ Watch it here: Better to be fast than to be right — Jessica Lin, Work-Bench, Not Another CEO Episode #102.

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

Conferences compound if you treat them as a content shoot, not a meeting sprint.

Most teams pack the calendar with 30-minute slots, fly home, and count the pipeline. Linear math. There’s a better way.

Get 30 minutes with five of your customers, film a casual on-camera Q&A, hand an editor the footage, and cut it into a month of captioned clips you drip out over LinkedIn and X. One YC team built its early GTM entirely this way.

The meetings are perishable. The footage compounds.

Conference ROI = pipeline booked once + distribution replayed for months.

Special shoutout to Finn Mallery, Founder of Origami, for this tip! Check out his post on it here.

✅ THE TO-DO

Pick five customers and four weeks before the conference reach out to those customers to schedule them for a casual on-camera Q&A. Let the conversation run naturally. Hand the footage to a freelance editor to cut into 15-20 clips for ongoing social media distribution.

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

Share

🤖 THE CLAUDE SKILL

The clips are the easy part; getting the right people into the room is the work. Paste this into Claude ~4 weeks out and it builds the whole runway to the footage: the outreach, the block, the film list, and the on-camera ask.

You are a B2B field-marketing strategist. I am running my GTM through one
conference and want to walk out with on-camera customer footage I can turn
into a month of content. Build the full plan to get there.

Conference: [NAME, DATES, CITY]
My product: [ONE LINE + the specific pain it removes]
Who I most want in the room: [TITLES / COMPANIES / ICP]
Customers or prospects already attending: [NAMES, or "none yet"]

Give me, in order:

1. PRE-CONFERENCE (4 weeks out): a public post announcing I'll be there and
   exactly how to reach me, the ~15 highest-priority people to DM, and 3 short
   DM templates I can personalize (warm customer, live prospect, cold target).

2. THE BLOCK: how to structure a 2-day meeting block. Venue type, how many
   30-min slots per day with buffers, and the one-line message I send with my
   booking link to lock a slot.

3. THE FILM LIST: from the people likely to attend, rank the 5 best on-camera
   subjects by how vividly they can name a problem I solve. For each, the one
   opening question that gets a real story instead of a testimonial.

4. THE ASK: a low-pressure, in-person script for inviting someone to a 15-min
   on-camera chat so it feels casual, not like a favor.

5. THE HAND-OFF: what to give my editor afterward to get 15-20 captioned clips,
   and how to sequence the drip so it feeds attention into my next conference.

📺 For Your Additional View

This week’s tip is about earning attention on camera, so here’s a fitting companion: the reminder that the first few minutes are where a VC’s conviction often forms. Our Jessica Lin sat down with our Work-Bench CEO-in-Residence David Politis on his podcast, Not Another CEO.

For founders, Jess calls out two key points to hit in your Seed pitch in the first 5 minutes:

1. Demonstrating velocity - how have you and your team moved fast, shipped, learned, iterated with early customers and pipeline 🚀

2. Articulate a big, ambitious vision that will take you 10 years to achieve - right from the jump 💥

See more of Jess’ post here and why founders should focus less on their current ARR and growth rate to $2M ARR - but be crystal clear on how they have a plan to $800M+ in ARR in the next 10+ years for a venture-scale business.

🎙️ Watch it here: Better to be fast than to be right — Jessica Lin, Work-Bench, Not Another CEO Episode #102.

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.

🌮 NY Tech Week - Join Us!

NY Tech Week is coming up the 1st week of June and we’re partnering up with our friends at Bling Capital, BBG Ventures, Correlation Ventures, and Springbank to bring great NYC founders, operators and investors together for a fun Taco Tuesday event with tacos, margaritas, and great connects. If you’re a new or longtime friend of Work-Bench, we’d love to see you there!

📍 Tuesday June 2nd from 6-9 PM | Sign up HERE

💡 THE TIP

Something to consider nowadays: you may need a different demo for different stages in your sales process:

• Vision demos (2–5 min) for exec wow moments and top-of-funnel

• Micro demos (30–120 sec) for BDR outbound

• Discovery demos (12+ min) for prospects already in cycle.

Demo length should be a function of where the buyer is, not a house rule about brevity.

Navattic’s State of Demo Automation 2026 report show that the best demos include 3–10 interest areas so buyers can self-direct.

Special shoutout to Natalie Marcotullio, Head of Growth and Product at Navattic and our very own Work-Bench Marketing Advisor, for this tip! Check out her post on it here.

✅ THE TO-DO

Pull your top three demo assets and ask one question of each: what stage of the buyer journey is this performing on? If you can’t answer in a sentence, you’re using the wrong demo for the wrong moment. Tag each with Vision / Micro / Discovery — and notice which stage you have nothing built for. That gap is worth focusing on.

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

Share

🤖 THE CLAUDE SKILL

Use this when you have one all-purpose demo and need to fork it into stage-appropriate variants.

You're helping me audit and re-cut my product demo into stage-specific versions for an enterprise sales cycle.

Context:
- Product: [BRIEF DESCRIPTION]
- Buyer personas: [E.G., HEAD OF DATA, CFO, IT SECURITY]
- Average sales cycle length: [WEEKS]
- Current demo: [PASTE DEMO SCRIPT, OUTLINE, OR LIST OF CLICKS/SCREENS]

Produce three versions:

1. VISION DEMO (2-5 min, for execs / top-of-funnel)
   - One "wow" moment that lands the category-level insight
   - Skip configuration, setup, edge cases
   - Output: a 3-5 beat storyboard with the single insight each beat delivers

2. MICRO DEMO (30-120 sec, for BDR outbound)
   - One specific workflow that solves one specific pain
   - Should be watchable without sound, on mobile, in a Slack message
   - Output: the workflow + the one-line subject hook to pair with it

3. DISCOVERY DEMO (12+ min, for prospects in active cycle)
   - 3-10 interest areas a buyer can self-select into
   - Goal: bridge the gap before the first SE call so that call goes deeper
   - Output: the interest area menu + what each one should leave the buyer understanding

For each version, also tell me: what to cut from my current demo, and what's missing that I need to add.

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

The SaaS industry built pricing pages for humans: three tiers, a comparison table, and a “Contact Sales” button for enterprise. It worked because the buyer was a person who could be guided into a demo.

AI agents don’t sit through demos. When an agent is evaluating vendors on behalf of a procurement team, it needs structured, machine-readable pricing, not a gated PDF. If your pricing lives behind a form fill or a sales call, you’re invisible to the fastest-growing buyer in B2B. While agents aren't making software purchases yet, it's plausible that they'll be more integrated in the process over the next couple of years, given the speed of AI innovation.

Teams building in this agent-first world: publish your pricing in structured formats (APIs, JSON, clear HTML) that an agent can parse without human intervention. The companies that do this first will win the deals that agents are shortlisting.

Special shoutout to Kyle Poyar for this tip! Check out his Linkedin post on it here.

✅ THE TO-DO

Go to your pricing page right now and try to extract your pricing tiers, feature limits, and per-seat costs using only copy-paste into a spreadsheet. If you can’t do it cleanly in 60 seconds, neither can an agent. That’s your gap.

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

Share

🤖 THE CLAUDE SKILL

Paste your current pricing structure and let Claude make it machine-readable.

Here's our current pricing structure:

[PASTE YOUR PRICING — tiers, features per tier, per-seat costs, usage limits, 
add-ons, enterprise pricing if you have it. Include anything that's currently 
behind a "Contact Sales" gate.]

Do three things:

1. Convert this into a structured JSON object that an AI agent could parse 
   to evaluate our product against competitors. Include: tier names, prices, 
   billing frequency, feature lists per tier, usage limits, and any 
   conditional pricing (volume discounts, annual vs. monthly, etc.)

2. Write a clean, parseable HTML pricing table that could replace our current 
   pricing page — designed for both humans and machines to read. No 
   "Contact Sales" gates on information that could be structured.

3. Flag what's missing: what pricing information would an AI procurement agent 
   need to shortlist us that we're currently hiding or making ambiguous? 
   (e.g., implementation fees, overage rates, contract minimums, SLA tiers)

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

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.

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

Share

🤖 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.

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

Share

🤖 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.

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

Share

🤖 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.

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

Share

🤖 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.

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

Share

🤖 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 😎

Share

🤖 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!