Most founders blow it. They either go deep on technical differentiation (nobody believes a 12-person startup out-engineers Anthropic) or they fold and start listing features they hope the prospect hasn’t Googled yet. Both moves lose the sale before it starts.

The right answer isn’t a feature comparison. It’s a workflow argument. And once you understand that distinction, this question stops being a threat and starts being a gift.

This post covers:

• How to reframe the question so you’re never playing defense

• How to map the full workflow your buyer actually lives in

• What falls outside Claude’s scope (more than you think)

• The two lines that close this conversation fast

• How to build toward an answer that gets harder to challenge over time

Reframe the question before you answer it

Claude is a general-purpose tool. It serves a billion users doing a billion different things. You serve one type of buyer solving one specific problem end-to-end. Those are not competitive products. They’re different categories.

The moment you let a prospect frame this as “your AI vs. their AI,” you’ve already lost. You’re playing on their turf, using their rules, and you will not win. The reframe is simple: “Claude is a tool. [your startup] is a workflow.”

Map your buyer’s actual workflow

Before you answer what Claude can’t do, you need to know what your buyer’s day actually looks like. Not the AI task in isolation. The whole thing: what happens before they need AI help, what they do with the output, who reviews it, where it lives, and what breaks if it’s wrong.

Most buyers using Claude directly are doing something like this: copy a brief into the chat, paste some context, iterate on the output for 20 minutes, then manually move the result into whatever system actually matters. That’s a workflow with Claude as one step in the middle, and a human doing everything else.

Your job is to show that you own the whole thing:

• What data does your product pull in automatically that they’d otherwise have to paste by hand?

• What does the output connect to downstream (a CRM, a compliance log, a review workflow, a formatted deliverable)?

• Who else is involved in getting this done, and how does your product support that handoff?

When you can walk a buyer through their own workflow and show them where the manual work lives, you’ve already answered the question. You just haven’t said “Claude” yet.

Show what falls outside Claude’s scope

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Visitors bounce, leads don’t come in, and somewhere in the back of your head you’re wondering if the market is just too early. It isn’t. What’s happening is your homepage is doing the one thing it should never do — confusing people.

This isn’t a design problem. It’s a clarity problem. The good news is its fixable.

This post covers:

• How to write messaging that actually lands with buyers

• What your headline, sub-headline, and product section should do

• How to structure your CTA, pricing, social proof, and lead intake form

• A full template for a B2B homepage

Your messaging is not for your investors

Most early-stage founders write copy for their investor deck, then paste it on their website. The result is a homepage full of sentences like:

“The AI-native platform for next-gen operational velocity.”

“Unlock synergistic workflows across your enterprise ecosystem.”

“The intelligent revenue acceleration layer for modern GTM teams.”

Nobody knows what any of that means. Your buyer doesn’t care about your architecture. They care about whether this thing will fix the problem they have right now.

Write for the person who’s going to approve the purchase. Not your co-founder, not your seed investors. Write for the VP of Ops who has 12 minutes before their next meeting and needs to immediately understand what you do and whether it’s worth a demo.

Plain language. Concrete outcomes. Zero jargon.

Your headline should describe what your product does for your customer

This is not the place for brand poetry. The headline is the first thing someone reads. If they don’t get it, they leave.

Bad headlines:

• “The future of team collaboration” Says nothing. Every SaaS company has said this.

• “Work smarter, not harder” A bumper sticker, not a value proposition.

• “Powering the modern workforce” Powering it to do what?

Good headlines:

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Sure the candidate could write what looked like a decent cold email and were energetic in the interview. They even talked a good game about “owning the top of funnel.” But what they’d never done was show up on a Monday with no playbook, no manager checking in, and a quota that was entirely their problem to solve.

There’s one filter that predicts success in this role better than anything else: has this person operated inside a very early-stage startup before? Not a 200-person Series B. Not a scrappy team inside a big company. A true pre-seed or seed stage startup where the process and tooling didn’t exist yet and they had to build it.

This post covers:

• The two filters to screen all applicants

• The interview questions that separate doers from talkers

• A take-home project structure that shows you exactly what you’re getting

• Founders Associate job description template

Two filters to screen all applicants

1. Seed or early-stage startup experience. Not as a buzzword on their resume but a chapter where they were doing outbound in an unstructured environment.

2. Prior experience as an SDR, BDR, or a comparable outbound role where they were actually booking meetings, not just “supporting sales”, or “supporting the founder”.

If you only have one, take the early-stage experience. You can teach someone your sequences and your ICP but you cannot teach someone to function without a safety net.

As much as I love giving people a chance to succeed, the failure rate on lack of

Screen for both upfront and don’t let an enthusiastic candidate talk you past this filter in the first call.

Get specific about their day-to-day

Don’t start with “tell me about yourself.” Ask them to walk you through their current day-to-day in detail. What do they do at 9am? What tools are they in? How do they decide who to reach out to? What does hitting their number actually look like?

This question does two things. It immediately separates people who have lived the role from people who’ve read about it who are searching real-time on ChatGPT while talking to you.

And it tells you whether they’ve been operating or just showing up. The best candidates get specific fast—tools, cadences, numbers, friction points. The ones who haven’t really been in it stay vague and abstract.

Also tells you if they are a good communicator. Can they communicate succinctly under pressure.

Ask the quarter question

Before you go any deeper, ask this 3-part question:

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The problem isn’t the content. It’s the approach. Dumping information on someone and expecting self-directed implementation doesn’t work. They need structure, repetition, and someone checking their work, not a reading list and good vibes.

The reality in sales management is that you can’t rely on continually recruiting sales superstars as you grow. You have to be able to turn an average to good seller into a good to great seller and doing that requires a great training program.

This post covers:

• How to split training into two distinct tracks (and why this matters)

• How to diagnose which reps need what training

• The weekly training cadence that actually builds muscle memory

• How to run role plays that don’t feel like theater

• How to use certification to tie skill development to career progression

Split your training into two separate tracks

Most programs lump everything together. Product knowledge, objection handling, discovery questions, pricing conversations — all one big blob of “sales training.” That’s how you end up with reps who can demo the product beautifully but still can’t book a follow up meeting to get a decision.

Separate it cleanly into two tracks:

• Product training: This is what you sell. Features, use cases, competitive positioning, how customers actually use the product. This is mostly knowledge transfer.

• Sales skills training: This is how you sell. Setting agendas, running discovery, handling objections, presenting pricing, negotiating, laying out next steps, booking the next meeting. This is behavior change, which is a completely different animal.

These require different content, different formats, and different measures of success. Mixing them creates reps who know a lot and do very little of it correctly.

Diagnose the gaps before you train

Before you build a curriculum, figure out who’s weak in which areas. You already have the data, you just need to use it.

Grab 5 call recordings per rep. Listen for key signals:

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The problem isn’t your product. It’s your process. RFPs are a structured buying exercise, and if you don’t have an equally structured selling process to match, you’re just filling out a form and praying.

I’ve watched companies with genuinely better products lose RFPs to inferior competitors because the winning team showed up more prepared. The good news is its not hard to stand out with a little effort.

This post covers:

• How to decide which RFPs are worth your time (most aren’t)

• How to staff and run a response without it becoming a fire drill

• How to build win themes that actually influence the decision

• How to avoid starting from scratch every single time

• What to do after you hit send

Stop responding to RFPs you can’t win

The most expensive thing you can do with an RFP is spend time on it when the buyer has already made their mind up to go with a competitor and is just using you as a filler in their process.

The immediate signs to look out for are:

• No relationship access. If you’re a complete outsider with no prior contact, you’re probably just filling out a form for the incumbent’s reference check.

• No opportunity to submit clarifying questions. If they won’t let you ask questions the process usually has a predetermined outcome.

• Overly prescriptive technical requirements. Especially when they eerily describe a particular vendor’s product. I know because I’ve done exactly this.

• Extremely short timelines. Tells you the decision has been made but the buyer is scrambling to show they got at least 3 quotes.

• Poor deal economics. The budget has to justify the effort. A $40K deal that takes three weeks of cross-functional effort isn’t a win even if you win it.

Walking away from a bad RFP is a legitimate call. There’s no point spending time on it if you know you aren’t going to win it.

Every RFP needs a deal owner and assigned roles

Disorganized RFP responses are almost always an ownership problem. Everyone thinks someone else is handling the security and privacy sections. Nobody owns the executive summary until the night before the deadline.

Fix it by assigning roles:

1. RFP Lead / Deal Owner. The AE or VP Sales. This person has final accountability for the response and the go/no-go call. They also write the executive summary, because they’re closest to the deal.

2. Project Manager. Sales ops. Owns the timeline, tracks tasks, and makes sure nothing falls through. In a smaller GTM team, this role is done by the deal owner, which underscores the importance of ignoring RFPs that you can’t win.

3. Solution Architect. Your pre-sales or SE lead. In smaller companies, the CTO. Owns the technical narrative, integration questions, and architecture sections. Need to be able to connect your technical capabilities to the RFP requirements.

4. Subject Matter Experts. Product, security, legal. Narrow the scope, with specific questions and tight deadlines. Don’t loop them into the whole process.

5. Executive Reviewer. The VP Sales or CRO does one pass at the end, looking for clear win themes and differentiation, not just typos.

Work backwards from the RFP deadline

A 2-week response cycle is manageable if you sequence it properly. Most teams don’t, they front-load coordination and back-load writing, which means the actual response gets written in a panic during the final 48 hours.

Here’s the sequence that works:

Days 1–2: Intake and kick-off. Log the RFP in your CRM. Distribute the document. Hold a kick-off call where scope gets reviewed, owners get assigned, and the timeline gets locked. Submit clarifying questions to the prospect immediately. Most RFPs allow them, and the answers often change how you approach the response.

Days 3–5: First draft. Pull from your content library (more on this below). SMEs complete their assigned sections. The solution architect writes the technical narrative. Pricing prepares the commercial section. Nothing gets polished yet — the goal is completeness, not perfection.

Days 6–8: Review cycle. PM checks for completeness. SE validates technical accuracy. Legal and compliance do their pass. The deal owner and executive reviewer look at win themes and overall messaging. This is also when you catch internal contradictions where the product team is saying one thing, the SE saying another.

Days 9-11: Final polish. All edits incorporated, conflicts resolved. Proposal writer does a copy edit and formats the document. The executive summary gets written last because it’s a synthesis, not an introduction.

Days 12-14: Buffer and submission. Final sign-off, submit at least 24 hours before the deadline, and confirm receipt with the prospect contact.

How to build win themes

Most RFP responses answer questions. The best ones tell a story where the prospect’s problem is the setup and your product is the resolution. Win themes.

Before writing starts, align the team on three or four win themes. These aren’t marketing taglines, they’re the strategic bets you’re making about what this evaluator cares about most.

How to develop them:

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Then you start the job. And you realize the hard part wasn’t in fact the getting in. It was that nobody warned you what you were walking into.

You go from being the best performer on the team to being the below-average manager of a team that just lost its best performer (You). And you still have a team quota to hit, starting immediately. There’s a reason half of new sales managers fail or quit within their first year. The skills that made you a great AE are almost entirely wrong for this role.

This post covers:

• The four mistakes that will get you fired

• How to build your analytical foundation

• How to create process discipline on your team

• How to develop a coaching system that actually works

• How to use delegation to develop your team — not just to offload work

The four mistakes that will get you fired

1. Doing everything yourself. Your instinct is to jump in. A deal is slipping, you take the call. A proposal looks weak, you rewrite it. A prospect goes dark, you personally follow up. This feels productive. It isn’t. You’re not developing your team, you’re doing their jobs for them, and you’ll burn yourself out doing so.

2. Telling your team to do it your way. What worked for you won’t work for everyone. Different sellers have different strengths, different communication styles, different gaps. Your job is to close those gaps, not to clone yourself. The moment you say “just do it like I did,” you’ve stopped coaching and are on a slippery slope back to trying to it all yourself.

3. Managing by what you hear instead of what you see. Your reps will tell you the deal is moving. They’ll tell you the prospect is engaged. They’ll tell you legal is the holdup. None of that means anything until you look at the data and listen to the calls yourself. You cannot coach what you haven’t observed. Coaching decisions made from secondhand information are just guesses.

4. Fighting fires instead of preventing them. Without a clear picture of your metrics, you manage whoever is loudest. The rep who complains the most gets the most attention. The deal that creates the most panic gets the most resources. You become reactive, not strategic and that’s not leadership; its triage.

Build your analytical foundation first

Data gets overwhelming fast. The fix isn’t to look at fewer metrics, it’s to look at the right ones.

Start by mapping your customer journey. Document every stage from first contact to closed-won. Make each stage concrete. If two people can’t agree on whether a deal belongs in a stage, the stage definition is broken.

Once you have the stages, pick two metrics per stage — one volume metric (e.g. how many deals entered this stage this month) and one conversion metric (e.g. what percentage moved to the next stage). That’s it.

Now look for the problems:

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This happens when reps have discount authority without guardrails. In their minds, the deal outcome is binary and giving the maximum discount is what tips it. That’s the wrong mental model and it’s your job as a sales leader to replace it.

The fix isn’t as simple as taking discounts off the rate card and forcing them to ask for approval. It’s changing what happens upstream of discounts even being discussed.

This post covers:

• The four things every rep must know before mentioning the price

• How to frame the price and get comfortable with silence

• What to do when a buyer pushes back on price

• How to tie discounts to dates and build urgency that doesn’t feel fake

• How to setup a deal desk so reps stop freelancing on price

Don’t mention price until you know these 4 things

Before a rep mentions a price they need to know four things:

1. The specific pain. Not a vague statement that “they want to improve efficiency”, nor a regurgitation of your value prop, “they want to leverage AI”. It needs to be something specific, described using the customer’s own words. If you can’t describe the pain in your customer’s language, you haven’t done discovery.

2. How often that pain shows up. A problem that happens once a quarter is an inconvenience that can be solved with a workaround. A problem that happens every week eventually becomes intolerable and turns into a budget item. Frequency determines urgency, and urgency determines whether price even matters.

3. The unit count. Seats, locations, transactions; whatever drives your pricing. This isn’t just about preparing the quote, it’s about surfacing whether the buyer is thinking about this at sufficient scale to justify buying a solution.

4. The critical event. A deadline or existing goal that your champion can use to ask for resources/money. "Q3” is not a deadline, its a placeholder. “We need this live before our board meeting on June 12th” is a deadline. “We’re thinking about how to use AI” isn’t a goal, whereas “We have a mandate to find 20% cost savings this year using AI” is.

Anchor on your list price, not the discount

Most AEs present price like they’re bracing for impact. They soften it, caveat it, and even lead with “we can be flexible” before the prospect has heard the number.

Stop doing this.

Discounting is a tool, not the opening bid. When a rep anchors on the discounted price, they’ve given away the margin before the negotiation starts and they’ve trained the buyer that the list price is bullshit.

Present list price confidently by framing it in terms of what your buyer told you in discovery e.g.

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By the time you’re six months into implementation, you’re underwater and the customer is disappointed in a product that was never designed to do what you promised. The relationship is worse than if you’d said no in the first place.

The counterintuitive truth is that customers don’t remember that you said no. They only remember that you didn’t deliver. Here’s how to avoid it.

This post covers:

• How to reframe a feature request before you react to it

• How to use your existing customer base as a reality check

• How to pressure-test requests with data before they make it onto a roadmap

• How to build a backlog that makes customers feel heard

• How to phase solutions so deals close, without commitments you can’t keep

Most custom requests aren’t actually custom

Whenever a customer asks you for something that sounds custom, your first question should always be, “What problem are you trying to solve?”, not “What do you want?”, or “How do you want that to work?”

Most custom feature requests are solutions your buyer has half-designed in their head and gotten overly-excited about. Your job is to put on your PM hat and walk them back from the edge by clarifying the problem rather than engaging in the solution.

Many requests are workarounds for something your product already handles differently. In that case the gap isn’t in your product, it’s in how they understand it. A good discovery conversation followed by a tailored demo or training session closes that gap without a single line of custom code.

Use your customer base as a reality check

Turn the feature request into a benchmarking moment by saying something like: “Most of our customers solve that problem like this _________ . How does that compare to how your team operates?”

Doing this accomplishes two things. First it grounds their request as an outlier in a broader reality, which signals that this may not be as universal a need as they think. Second, you show that you see patterns across accounts, which demonstrates the depth of your understanding and builds credibility.

If their answer is “actually that’s the same for us,” you may have just diffused the whole request. If their answer is “we actually do it differently,” you’ve just learned something useful and can move onto the next test.

Pressure test with their own data

Customers tend to overweight the importance of edge cases because they consume disproportionate mindshare — the unusual is more exciting than the mundane. Your job is to re-balance this against the 90% of their business that already runs smoothly but never comes up in conversation.

3 questions to ask to do this are:

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Traditional SEO is a ranking game, where you’re competing for position on a results page that a human then chooses to click. By contrast, GEO is a citation game, where you’re competing to be the source an AI model references when it generates an answer. No click required, no position one to aim for. It simply comes down to, does the model trust your content enough to quote it.

That shift sounds subtle but it isn’t. A 2025 analysis of 300,000 keywords found that AI Overviews correlate with a 34.5% drop in average CTR for the #1 organic result compared to similar queries without them. The traffic model is breaking. If you’re still measuring success purely through rankings and click-through rates, you’re optimizing for a game that’s getting smaller.

This post covers:

• What actually changes between SEO and GEO; ranking vs referencing

• The 9 tactical shifts that matter, with examples of how to implement them

• Where GEO and SEO genuinely overlap

• An honest state of where GEO is right now

The shift from being ranked to being referenced

In traditional search, your own well-optimized pages could rank on their own merit. Write good content, build some links, structure it properly, Google notices, users click.

GEO doesn’t work that way. AI search shows a systematic bias toward earned media over brand-owned content. Much stronger than traditional search algorithms ever did. What you publish on your own domain matters less, whereas what gets written about you, by sources the model already trusts, matters enormously.

That’s the biggest strategic reorientation. Not a tactical tweak.

9 tactics that move the needle

1. Earned media is your highest-leverage investment

Getting placement in authoritative industry lists, round-ups, and third-party reviews isn’t a PR nice-to-have anymore. It’s a primary acquisition channel. When AI engines are asked to recommend tools in your category, they pull from sources they trust. If you’re not in those sources, you’re invisible.

This is the sharpest break from traditional SEO. Own-site authority still matters, but it no longer carries the conversation.

2. Write for machine scannability, not for human delight

AI search engines don’t surface the most insightful content. They surface the easiest-to-parse content. Practically, that means:

• Short paragraphs of two to three lines max.

• Bullet points and numbered lists wherever a sequence exists.

• Lead each section with one or two sentences that directly answer the heading.

• Use a consistent answer pattern: definition → detail → example.

Semrush’s research confirms this. Structure beats prose when machines are the primary consumer.

3. Target conversational queries, not typed keywords

The way someone prompts ChatGPT is different from how they’d type a Google query. Traditional keyword tools miss this entirely. “Best CRM for SMB” becomes “what CRM should a 20-person B2B company use if they’re moving off spreadsheets.”

You need to research how your audience actually phrases questions to AI assistants and then write content that answers those specific phrasings directly.

An easy way to do this research is to ask each LLM, "What questions do people ask about [your topic/product category]?" or "How would someone ask an AI assistant to help them find [your type of product/service]?" The models will surface natural language patterns they've been trained on.

Another way is to filter your Google Search Console queries for long-tail, question-based queries (anything starting with "how," "what," "why," "best way to," etc.). These are the closest proxy for AI-style queries, and they'll show you what's already driving impressions even at low volume.

4. Make your content quotable

AI-generated answers are essentially assemblies of citations. The content that gets cited is content that can be dropped in without editing; concise definitions, clean numbered steps, specific observations that stand alone.

For example, imagine you are trying to show up in AI results for the question, “what is project management software and why do teams use it?”:

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The mistake most founders make is treating this as a pricing negotiation. It isn’t. It’s a risk psychology problem dressed up as a procurement conversation. The buyer isn’t trying to get a discount—they’re trying to protect themselves from looking stupid in front of their CFO six months from now. Caving on price doesn’t solve that. It just makes you cheaper and still loses the deal.

Here’s how to actually handle it.

This post covers:

• How to diagnose what the buyer is actually afraid of

• A two-tier license structure that resolves the commitment standoff

• How to build a rollout plan that sells itself internally

• A template you can steal

Diagnose the real objection

Before you restructure anything, figure out what you’re actually dealing with. There are two types of hesitation, and they require completely different responses.

The first is procurement theater. “The space moves quickly” and “we don’t want to be locked in” are negotiating lines—not real blockers. If you hear these from a VP of Finance you’ve never met who just joined the call, that’s theater. Push back: “If the space didn’t move at all, would you commit to annual?” Watch what happens.

The second is genuine internal risk. The champion likes your product but is worried about sponsoring a tool that gets replaced in 90 days. They’re not scared of overpaying—they’re scared of looking bad. That’s a political problem, and no discount fixes it.

Once you know which one you’re dealing with, you can respond to the actual objection instead of the stated one.

Build a two-tier license structure

Stop trying to force every buyer into a single contract type. The structure that works is simple:

• Annual committed licenses — lower per-seat price, unlimited usage, full production access. For teams that have already validated value and are ready to commit.

• Evaluation licenses — monthly, usage-capped, priced 20% higher than the annualized equivalent. For teams that haven’t piloted yet and need a structured on-ramp.

The pricing differential matters. If evaluation licenses are cheaper or equivalent to annual, you’ve just given buyers a permanent workaround to avoid committing. Price them higher—not punitively, but enough that committing is the obvious rational choice once a team has validated the product.

Cap the usage on evaluation licenses aggressively enough that buyers can assess value but can’t run production workflows on them. If someone can do their full job on an evaluation license, they will—and you’ll never convert them.

Write the rollout plan before you send the proposal

This is the part most founders skip, and it’s the most valuable thing you can do in a complex enterprise deal.

A rollout plan is a one-page document that shows by team, by quarter which groups start on annual committed licenses, which groups start on evaluation licenses, and when each evaluation group converts to annual. It answers the question every internal champion eventually has to answer upward: “What does full deployment actually look like?”

Build it before the proposal goes out. Use what you know from deal conversations to date i.e. which team piloted, which teams are next and what their rough timelines look like. Make it concrete with real team names and real dates.

The rollout plan does three things at once:

1. It gives your champion something to present. Internal approvals require internal selling. A concrete deployment plan is a better artifact than a quote.

2. It de-risks the purchase for finance. The CFO isn’t worried about this quarter’s spend, they’re worried about runaway expansion with no governance. The rollout plan shows there’s a process.

3. It locks in the expansion conversation before the deal closes. You’re not just selling the pilot team. You’re selling the whole org on a timeline.

You’re not solving a pricing problem with this document. You’re solving a political one.

Set a quarterly true-up cadence

Monthly billing reconciliation on flexible licenses creates admin overhead that kills relationships fast. Move everything to a quarterly true-up cadence. Every 90 days, you reconcile usage, convert any evaluation licenses that hit the conversion criteria, and adjust seat counts.

This gives buyers the flexibility they think they need while giving you the predictability you actually need. It also creates a natural checkpoint to revisit expansion without making it feel like a sales call every month.

Cap monthly active users

One guardrail that doesn’t get talked about enough: cap the monthly active users (MAU) on evaluation licenses, as well as the usage itself. Without a cap, buyers will quietly use evaluation licenses for real production work across their entire org and never convert.

An MAU cap keeps evaluation licenses working as intended i.e. a structured assessment window, not a permanent workaround. Set the cap at a number that’s enough for a real pilot but not enough to scale across a department.

The rollout plan template

Most enterprise deals that stall on the buyer saying, “we’re not ready to commit” aren’t really about commitment. They’re about a champion who doesn’t have enough cover to go to bat for you internally. The two-tier license structure buys them time but a rollout plan buys them credibility to get the deal done.

Here’s a template for the rollout plan and instructions for how to adapt it and how to use it in your deal conversations:

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The conversion problem isn’t awareness. It’s signal. You have no idea who’s behind those downloads, and GitHub isn’t going to tell you. It could be a mid-market product team that’s been hacking together deployment scripts for six months and is one production incident away from buying a real solution. Or it could be a grad student who downloaded your framework for a class project. Treating those two the same is how you waste six months of sales motion on the wrong people.

Here’s what actually works.

This post covers:

• Why most open-source users will never buy and how to stop chasing them

• How to build visibility into an anonymous user base

• How to qualify for commercial potential, not just enthusiasm

• How to use community channels to surface real pain

• How to structure a concrete upsell path that closes

Most of your open-source users are not your customers

Open source functions as a freemium front door. It’s excellent for research adoption, benchmarking, and getting your framework embedded in early-stage technical decisions. It’s terrible for direct conversion if you don’t do the work to figure out who’s actually behind the usage.

Two groups will never buy from you but they’re often the loudest in your community:

• University researchers. No budget, no infrastructure headache at scale, and often a cultural disposition toward building over buying. They’ll contribute PRs and open issues and love your product. They will not send you a PO.

• Not-invented-here engineering teams. These are deep-technical, engineering-led orgs that genuinely enjoy building infra. They treat your open-source framework the same way they treat everything else: a starting point for their own custom system. You’re not losing them to a competitor. They just aren’t buyers.

Stop optimizing for these groups. They inflate your community metrics and dilute your pipeline signal.

Build visibility into your anonymous user base

Accept the constraint upfront: GitHub downloads give you a number, not a customer list. You cannot build a sales motion on a download count.

The fix is straightforward, but most teams skip it because it feels like friction—and they’re worried about slowing adoption. Don’t be. The teams with real deployment problems will still show up. You’re not filtering out buyers; you’re filtering out noise.

Here’s how to surface real identities:

• Waitlists for early access features. Gate your most useful production-grade features behind a lightweight signup. You get an email, a company, and a reason they’re interested.

• Community onboarding in Discord or Slack. When someone joins, ask them one question: “Are you using this for research, a side project, or something in production?” You’ll be surprised how directly people answer.

• Early access programs tied to specific use cases. “Apply for early access to our monitoring module” tells you exactly who’s trying to solve a real operational problem.

None of this is complicated. The good news is the bar is still low as most open-source companies aren’t doing any of it.

Qualify for commercial potential, not just interest

Not all users with real jobs at real companies are buyers. You need to segment, and you need to do it early.

The segments that matter:

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And yet founders keep defaulting to it. The logic goes: build a big list, drop in a template offering some asset, turn the sequence on, and watch the replies roll in. Spoiler alert, they don’t.

The good news is you almost certainly have data sitting in your CRM and analytics tools right now that can get you 5–10x better reply rates than basic cold email. You don’t need to hand-research every prospect to craft the perfect message. You just need to segment prospects by psychological state and write copy that meets them where they actually are.

This post covers:

• Why psychological state is the only segmentation variable that matters

• 7 psychological segments you can build from your own first-party data

• Email messaging templates for each segment

• Sequences and subject line tests

Relevance beats volume every time

The reason most outreach underperforms has nothing to do with deliverability or send time or whether you used their first name in the subject line. It’s that the message doesn’t match where the person is in their head.

Someone who ghosted you after a demo is in a completely different mental state than someone who filled out a form but never booked. Treating them the same way with the same template, the same offer, the same tone is leaving money on the table.

Each of the 7 segments below has a distinct emotional context. Match the copy to that context, and your reply rate will stop being embarrassing.

7 segments

1. Closed lost - timing not right

These are your warmest leads. They didn’t reject you, they rejected the timing. That’s a fundamentally different no, and it deserves a different response.

A low-pressure, short “checking in” message is all you need here. The goal isn’t to re-pitch. It’s to reopen the door and see if the conditions have changed. Don’t recap your entire value prop. Don’t attach a case study. Just acknowledge where things were, note that circumstances change, and make it easy for them to raise their hand.

Overselling here actively hurts you because it signals you don’t remember the conversation, which destroys the rapport you built during the original deal.

2. Closed lost - price too high

Never lead with a discount. It tells the prospect you were overcharging them, which either confirms their suspicion or creates a new one.

What works instead is reframing the ROI or introducing a lower-commitment entry point e.g. a pilot, a stripped-down tier or a bundle that changes the maths. The goal is to make the economics feel different without signaling desperation. If you’ve genuinely improved your pricing model since the deal closed, by all means lead with that but if you haven’t, lead with the outcome they’d be buying, not the number.

3. Closed lost - feature gap

These contacts need to see proof, not promises. A message that says “we’ve improved a lot since we last spoke” lands with exactly zero credibility. Specifics do.

If you’ve shipped the feature that killed the deal, lead with that concretely. Name the feature, explain what it does, link to documentation or a short demo. If the feature still isn’t there, don’t waste time reaching out.

4. Closed lost - ghosted

Keep it short. A three-sentence email with a dead-simple yes/no CTA outperforms anything polished and long. Long emails go unread, especially from someone who’s already tuned you out.

The frame that works: pattern interrupt. Something that acknowledges the situation without assigning blame, creates a low-friction path to re-engagement, and respects their time. “Still worth a conversation?” is more effective than three paragraphs explaining why you’re still a great fit.

5. Booked demo - no show

Don’t ask why they didn’t show. You’ll come across as passive-aggressive, even if that’s not the intent.

Just make it easy to rebook. Acknowledge upfront that schedules get chaotic. It gives them permission to re-engage without embarrassment. Offer a specific slot rather than “let me know when works” so it removes one more decision from their plate. A time-bound nudge (”I have Tuesday at 2pm or Thursday morning”) performs better than an open-ended invite.

6. Filled the lead form - didn’t book a meeting

They raised their hand but something stopped them from taking the next step and it’s almost never the product.

The friction is usually informational: they don’t know how long the demo is, what they’ll actually see, or whether they’re about to get a 45-minute sales pitch dressed up as a product tour. Address those objections directly in the email. Add one line of social proof (a recognizable customer name, a specific outcome) to tip the confidence needle. You’re not re-selling, you’re removing the last obstacle between them and the calendar.

7. Site visitor - de-anonymized

This one requires the most care because these people have not opted in to anything. All they did was look at a page on your site. If you lead with “I saw you visited our pricing page,” you’ll come across as creepy/desperate.

The only play that works here is leading with value e.g. a relevant insight, a resource, or a point of view tied to what they were looking at. Build credibility before you ask for anything. If they were on your integration page, send something useful about the category they’re likely evaluating. Earn the right to the next conversation rather than demanding it.

Email templates

To get you started, I’ve put together templates for each of the 7 segments that meet the prospect where they are in their head. The templates are available to paid subscribers at the link below:

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Everyone assumes joining a successful startup is easier than a zero-to-one build. It’s not. The pressure is higher, the appetite for failure is lower, and the company keeps growing whether you’re adding value or not. Nobody’s waiting on you to save the business, which means nobody notices if you’re quietly spinning your wheels.

The biggest mistake first marketing hires make is going top-of-funnel too fast. They launch brand campaigns, redesign the website, build out a content calendar, all before understanding what’s already closing deals at the bottom. Months pass, budgets burn, and the sales team is no better fed than the day you walked in.

The fix is to do the opposite. Start at the bottom of the funnel and work your way up.

This post covers:

• How to define the one metric that actually matters

• What to do in week one before you open a single Google Doc

• How to map the inbound engine before you touch it

• Why your first campaign should amplify, not invent

• How to put a real number in front of the team within 30 days

Define your north star metric before you do anything else

Your first conversation with sales leadership should produce one thing: a single shared KPI that everything you do gets measured against.

At an inbound-led B2B company, that number is almost always demos booked — not leads generated, not MQLs, not traffic. Leads are a vanity metric until someone picks up the phone. Every campaign you run, every channel you test, every piece of content you publish gets judged against demos booked. If it doesn’t move that number, it doesn’t matter.

Get this aligned in week one. If sales and marketing are optimizing for different things, you’ll spend six months producing work that impresses no one.

Spend week one in listening mode, not planning mode

Get into the Slack channels where deals are actually won and lost.

Find the deal negotiation threads, the closed won alerts, the closed lost alerts and the demo booked alerts. Read them obsessively for a week. It’s market research better than any win/loss survey or customer interview program and you don’t have to build anything to do it.

What you’re listening for:

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The real moat against a cheap incumbent copycat isn’t just price and feature parity; it’s a combination of usage habits, proven value, additional hooks into painful adjacent workflows and flipping the loss-leader logic.

Here’s how:

• Segment your customers to identify your risk

• Polish your ROI story

• Flip the loss-leader logic with an 80% copycat of your competitor

• Run a targeted customer success motion

Segment your customers to identify your risk

Use a simple 2x2 where each quadrant represents a distinct customer type based on how much they use your product and how sensitive they are to price:

Choose the most applicable of the following options to define your high/low break points for usage:

• 70%+ of licensed seats provisioned and used

• Consuming 60%+ of plan tier usage limit

• Adopted 60%+ of key features

Choose one or more of the following to define high/low break points for price sensitivity:

• Has (or has requested) a discount

• Is on a month-to-month contract if your standard is annual

• Bottom quartile of ACV

Polish your ROI story

Document the core value drivers of your product and the ROI you’ve driven to date. Common examples are:

• Incremental revenue generated (jobs done x revenue generated per job)

• Total time saved (jobs done x time saved per job)

• Qualitative feedback from your most active users. Set up 1:1s with them and ask, “How has your day-to-day changed since you started using [product]?”

More on this topic here:

Design an “80% copycat” of your competitor’s product and flip the loss-leader logic

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While this can seem like an immediate deal-killer the reality is you can still close the deal while your SOC 2 is still in progress. What actually wins enterprise deals is confidence, documentation, transparency, a predictable roadmap and no surprises. Basically make it boring and procedural.

Here’s how:

• Control the narrative early

• Build a SOC 2-in-progress security packet

• Anchor on risk, not on checking the box

• Offer compensating controls

• Use social proof and exec pressure strategically

• Separate security review from legal review

Control the narrative early (pre-questionnaire)

Don’t wait for procurement to escalate your lack of SOC 2 Type II. As soon as the deal starts moving, bring it up proactively:

“We’re currently in the final stages of SOC 2 Type I, with Type II following. I’m happy to share our control matrix, policies, and timeline.”

This signals maturity, prevents surprise objections and keeps you in control.

Build a SOC 2-in-progress security packet

Buyers mainly want proof you know your risk surface. Create a reusable folder that includes your:

• SOC 2 timeline: date the auditor was engaged, audit period dates, expected issuance date and Type I vs Type II clarity

• Control matrix: covering security, availability, processing integrity, confidentiality and privacy.

• Core policies: for access control, incident response, data retention, secure SDLC and vendor management.

• Subprocessor list: include vendors like AWS, Stripe, Open AI

• Pen test executive summary

Anchor on risk, not on checking the box

Security teams ultimately care about risk transfer. Your controls matter more than the Type II certificate itself.

Frame your response as:

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They’re so full of jargon, hyperbole and recently-invented categories-of-one that the visitor is left asking themselves, “WTF does this company actually do?"

I give you Exhibit A:

…and Exhibit B:

…and Exhibit C:

Don’t leave your visitors scratching their heads. Instead do the following:

• Get your headline right

• Explain how it works (in plain language)

• Drive to a single call to action

Get your headline right

Your headline (and sub headline) is the first thing your visitors see, so it needs to instantly communicate what you do. Start with a customer-centric, literal headline that communicates either the job you do or the specific outcome you deliver in one, short sentence. Then use a sub headline to clarify either how it works or whom it is for in one, longer sentence.

Here are some great examples of headlines and sub headlines (all at seed-stage companies):

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In my experience, a lot of startups have poorly structured agreements because a lot of startup founders’ lawyers reuse old contracts to save time on drafting without adequately reflecting on how realistic the contract is for their client’s size and stage.

This post lays out eleven best practices for structuring your agreements as an early-stage startup to ensure a speedy legal review. Note that this post is not legal advice. I am not a lawyer. Think of it more as a checklist to evaluate your current paperwork and discuss it with your own lawyer.

1. Use a separate Master Services Agreement (MSA)+ Order Form to speed up review.

Doing this separates your legal terms (in the MSA) from your commercial terms (in the order form), allowing for each document to be reviewed and negotiated by the relevant expert (the MSA by a commercial affairs lawyer, the order form by finance/procurement) and reduces the likelihood of lawyers trying to become procurement heroes and vice-versa.

2. Write in plain language to reduce misinterpretation

Lawyers distrust unclear drafting and will respond with heavy edits. To avoid this happening write in short sentences, make minimal use of defined terms, avoid triggering terms like “including without limitation” and “sole discretion” and avoid confusing double negatives such as “fail not to”, “not uncommon”, “cannot not” and so on.

3. Start from market-standard positions to avoid redlining battles.

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There are two ways to measure the ROI of a product. Either you show how much it increases revenue or you show much it reduces expenses. However, many sellers make the mistake of thinking there’s also third way — showing how much time it saves — only to get shot down when their deal hits the CFO’s desk for approval.

In this issue:

• How to show the ROI based on increasing revenue

• How to show the ROI based on reducing expenses

• How to show the ROI based on saving time

How to show the ROI based on increasing revenue

If your ROI story is based on increasing revenue, you need to be able to prove it directly and quickly in a time-limited trial in order to have a predictable motion for customer acquisition.

For example, my client Ajax is an AI timekeeping solution for mid-size law firms which finds billable hours that were missed and attributes them to the relevant matter. To show the ROI, the Ajax sales team runs a pilot with new customers to track how many incremental hours the software finds, divides the value of the additional billable hours by the cost of the software and shows a healthy return on investment (typically 10x or more), making it an easy decision for the buyer to approve. After all, who doesn’t love found money.

How to show the ROI based on reducing expenses

If your AI product replaces an existing legacy tool at a lower cost the ROI story is fairly straightforward. The customer buys your product, rips out the old product and as long as the new and existing contract terms don’t overlap too much, they are guaranteed to reduce their overall expenses.

For example, my client Surface Labs has an AI solution for marketers that combines multi-step forms, lead nurturing, lead scoring, qualification and routing in a single product that replaces tools like Zapier, Chili Piper and parts of a CRM at a lower cost. This makes it an easy decision for marketers looking to consolidate vendors, reduce tool spend and increase website conversion.

How to show ROI based on saving time

If your AI product saves time, simply showing the amount of time saved is not enough.

Nor is simply asking your buyer, “What would you do with those time savings?” and using their answer, “We’ll be able to spend it on more important things” as your ROI justification. As a former COO, I lost count of the number of times people on my teams pitched me to buy salestech that would enable them to “spend more time selling” only to fold when I asked them if they’d be ok with a higher quota.

Nor is translating time savings into a dollar amount e.g. if each person on the team saves 10% of their time and makes $100k/year salary then the time savings are somehow magically worth $10k/year. This is meaningless unless the buyer is planning to reduce headcount.

The only way to predictably show the ROI from time savings is how it increases the capacity of an existing team without having to add more people to the team:

For example, several of my clients sell AI products that reduce the time taken to perform repetitive tasks; Scope reduces the time to produce industrial inspection reports, Fleetcraft reduces the time to complete aircraft maintenance paperwork, Henry reduces the time to produce commercial real estate pitch decks, Tracelight reduces the time to produce financial models in Excel.

For all of these companies the ROI story has a similar structure:

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