The tactics that work best are actually the ones that borrow trust or create awareness first. I work with seed and Series A founders every week, and the pattern is consistent: the closer your outreach is to a real relationship, the better it performs.

In this post I rank nine early-stage outreach tactics from worst to best, explain why each lands where it does, and show how to make even the weak ones work harder for you.

#9 Cold email

While email is the de-facto medium for B2B communication, its also saturated af. Email response rates have been on a downward trend for 20 years, thanks to vendors deploying automation after automation — AI SDR being the latest one — to send more emails to more people at higher frequencies.

A better approach for email is to treat it as an awareness channel:

• Cold call the people who open your emails. If you get a connect, there’s a slightly higher chance that they’ll have heard of you and not hang up on you. Admittedly you need to send a lot of emails to get any kind of signal.

• Start a newsletter. If you actually have valuable insights to share on a regular basis, a newsletter is an excellent way to stay top of mind without the cringe of pretending you noticed something about your prospect and that you have some valuable content that they can only get if they respond to your email.

• Skip sending emails altogether and use the same list to run a custom audience campaign on Meta. This will at least get people from your ICP coming to your website, which gives you a shot at connecting with them (as covered later in this list).

#8 LinkedIn messaging

While LinkedIn is less saturated than email because of rate limits on connection requests and inMails, its still a lot of paraphrased LinkedIn bio slop and pitch slapping.

A better approach for LinkedIn is to also treat it as an awareness channel:

• Post quality content to build an audience, attract your ICP and stay top of mind with them.

• Use a tool like PhantomBuster to download profiles who regularly like and comment on your posts to build a more targeted list.

• Boost your top performing posts to increase reach.

#7 Cold call to cold prospect

Cold calling is surprisingly good in certain categories but is very time consuming and needs at minimum dedicated time blocks if you’re a founder doing GTM on your own and at ideally a dedicate resource like a BDR or founders associate. I currently have several seed stage and Series A clients booking 20 meetings a month cold calling cold prospects.

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Traffic goes up. Spend definitely goes up. But pipeline stays exactly where it was. It’s what happens when someone with a deadline and a credit card is told that “we need to get in front of people” or “we need to fill the top of the funnel”

You need marketing that produces meetings now, and the fastest source of those is

This post covers:

• Why to start at the bottom of the funnel

• How to identify people who have raised their hand but not converted

• How to practice on free traffic before you start paying for it

• What to do when you turn on paid

Start with the bottom of the funnel, not the top

“Generating awareness” is lovely and all but if it isn’t generating pipeline, it’s wasted effort and you should measure it that way from day one. Forget impressions, clicks and engagements. Focus on pipeline, or more specifically: completed meetings with your ICP.

Most people start at the top of the funnel because that’s where the fun, creative stuff in marketing tends to happen. Instead start at bottom, immediately upstream of a meeting being booked. Whatever is closest to the meeting is always closest to the money and to building pipeline.

Turn on a visitor de-anonymizer

Use a tool like RB2B, Vector or Syftdata to identify who is already on your site. Even if it’s only one or two people a day. In fact, especially if it’s only one or two people a day, because that means you can actually do something about each of them.

Run the visitor data through an enrichment tool like Clay or Apollo to filter out visitors who are not your ICP and fire the alerts into Slack so and have your SDR, founders associate or even you (founder) call them within minutes. Minutes matter as a person who was reading your pricing page at 2:10pm has very probably not forgotten you by 2:15pm but by tomorrow they will have.

Script the call as if it were normal

The most common worry is that calling site visitors feels creepy. It doesn’t if you’re upfront from the start:

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You said yes, sent the deck, ended the call and thought, “great call, strong champion”. But three weeks later, nothing has happened and your emails are going unanswered. The deal is dead.

This post covers:

• What to do before the call, so you’re not guessing during it

• How to ask about other stakeholders without getting stonewalled

• What vague answers really tell you

• How to ensure the next step actually happens

Spoiler: none of this is rocket science. It just runs against the grain in a call that seems to be going well, which is exactly what stops people doing it.

Map the org before the call

A few minutes with LinkedIn, Sales Nav or Apollo is enough to build a rough sketch of who in the company is a peer, who’s a boss, and who sits in an adjacent team that may have an opinion.

You won’t get it exactly right. Titles are confusing. That’s fine. You’re not going for 100% accuracy. You’re going for not walking in blind, so that when they say a name, you know roughly how they’ll be involved in the buying process.

Don’t ask, “Who is your boss?”

That question always gets stonewalled because it sounds like you’re checking whether they’re important enough to talk to, or plotting to go around them. Tbf that’s exactly what you are doing that but you don’t want them to feel that.

Instead frame it as a logical step in the evaluation process:

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• “What piqued your interest when I reached out?”

• “What brought you in today?”

• “What’s top of mind for you at the moment?”

While there’s nothing inherently wrong with this approach, it gets inefficient for two reasons.

• It forces your prospect to do all the work of articulating their own problems, which leads to vague descriptions that require multiple clarifying questions.

• It opens the door to discussing problems that your product doesn’t currently solve, which immediately puts you in position of weakness having to backpedal.

The way to solve this is to use a menu where — just like in a restaurant — you tell your customers what people like them usually come in for and let them pick one. Here’s how to execute it:

Open by naming the common problems

The menu is the list of the 2-3 common problems you solve. Any more than that and it turns into a monologue that’s hard for your buyer to digest. (Note: even if you think your product solves 10 problems, the reality is 90% of your customers buy you for the same 2-3)

There are a couple of ways to structure this:

• “Well look, most of [persona]s I talk to are struggling with one or more of the following: [list the problems]”

• “Usually when [persona]s are evaluating [solution type]s, it’s for one or more of the following reasons [list the reasons]”

For example, when I do disco with founders exploring sales coaching, I say:

• “Most founders I talk to are struggling with one or more of the following: generating leads, closing deals or upselling existing customers”

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If this sounds familiar, you’ve probably had a customer tell you, “We love the product. Can we keep using it while the paperwork is sorted out?” It seems rude to say no but it’s no different from them asking, “We love your house. Can we live in it for free while we discuss whether we want to rent it?” You wouldn’t say yes to the latter. You shouldn’t say yes to the former.

This post covers six steps on how to avoid this happening. None of them are complicated but they are slightly uncomfortable, which is why this problem exists. Get comfortable being uncomfortable…

1. Define the grace period

Most pilot agreements say how long the pilot lasts and what it costs afterwards but very few say what happens at the moment it ends. It opens the door to an extension.

Decide in advance how long a grace period, if any you are going to offer. Don’t wing it and decide it deal by deal because you’ll get caught up in the emotion of hoping the deal will close.

2. Fire an in-product banner when the pilot ends

The ROI decision call typically marks the end of the pilot, so that’s when the banner should go up. It should be crystal clear about what is ending and what to do to maintain usage.

For example. if you are offering a 5-day grace period, the banner should say, “Your trial period ends in 5 days. After that you’ll lose access” and should decrement each day.

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The problem is that in the advisor’s mind they only signed up to show up once a month, share some wisdom and continue to vest the equity for the next two years. Fast forward six months, nothing has materialized so they quietly stop talking to each other.

It’s a shame when this happens because hiring the right type of advisor can actually be an excellent way to scale your warm intros way beyond your personal network and keep your top of funnel humming.

This post covers:

• How to decide what type of advisor you are hiring

• How to be upfront about what you need them to do

• How to screen out advisors who aren’t up for the job

• How to get value out of the one-win advisor

• How to structure the relationship

Decide what kind of advisor you are buying

There are 3 types of advisor for GTM. You need to know which one you’re buying

1. Introductions: someone who knows a lot of people in your ICP and is willing to introduce them to you.

2. Expertise: someone who has sold to your ICP and can advise you on how to build pipeline and close deals.

3. Branding: someone you can name drop to others to impress them.

Be upfront about what you are buying

An advisor whose job is making introductions is functionally not that different from an SDR. The difference with an advisor is that you have lower expectations on volume and higher expectations on quality.

Setting these expectations is the part that founders often skip because it feels rude to say to someone you admire, “I’d like to bring you on as an advisor because you know the right people. I need my advisors to make 2 intros a month. Are you up for doing that?”.

But it’s not an insult, it’s a job description for a role that many genuinely excellent people are happy to do. If they hesitate when answering it tells you everything you need to know — just part ways with them on good terms.

How to identify the right type of people for the role

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It lays out the 7 most common CRM issues, the benefits of fixing them and how to easily implement the fix in Hubspot/Attio/Salesforce.

1. Separate leads from deals

Leads represent prospects (people) that you would like to connect with, whereas deals are active conversations with prospects. You need to keep them separate because connecting with prospects (prospecting) and talking with prospects (closing) are distinct sales motions.

If you mix them together, like many founders initially do, you lose visibility into the results of your prospecting motion (connect rates from calling, emailing, going to conferences, inbound etc) and the results of your closing motion (sales cycle, win rate etc).

Don’t have a pipeline stage called Leads. Instead add the people as Contacts (Salesforce and Hubspot) or People (Attio) and the company they work for as Accounts (Salesforce) or Companies (Hubspot or Attio). Make sure you associate each person with the company they work for so that you can easily see all the people at the target company (prospecting always works better when you have >1 contact per company)

2. Use as few deal stages as possible

Let’s start with deal stages you don’t need

• Stages that track lists of Leads e.g. Conference, Key Targets, Strategics. These should be lists of people and companies as described above.

• Stages to track tasks e.g. Meeting Complete, Demo Complete, Proposal Sent. These don’t tell you anything about how your deal is actually progressing, only that you’ve gone through the motions on your end.

• Stages to track the number of meetings e.g. 1st meeting, 2nd Meeting, 3rd Meeting. These also don’t tell you how your deal is actually progressing and you don’t need stages to track how many meetings you’ve had.

• Stages to track stalled deals e.g. Pending SOCII, Nurture, Not Qualified, Ghosted. These can be combined into Closed Lost, with a loss reason used to explain why. Remember closed lost now does not mean closed lost for ever.

Here are some typical pipeline stages and how to choose the one that is right for your business. Note how the stage names are numbered — it makes it easier to analyze the data:

• 4-stage pipeline: 1. Discovery → 2. Proposal → 3. Closed Won → 4. Closed Lost. Use if you’re selling services in a process where you have one or two discovery calls, a proposal review call and a yes/no decision call.

• 5-stage pipeline: Couple of flavors:

  • 1. Discovery → 2. Proposal → 3. Pilot/Trial → 4. Closed Won → 5. Closed Lost. Use if you’re selling software in a process where you run a free pilot before getting into an annual contract. Very common with AI startups because AI is still relatively new and most customers want to try it before they commit.

  • 1. Discovery → 2. Demo → 3. Proposal → 4. Closed Won → 5. Closed Lost. Use if you’re selling software where you run a custom demo using the prospect’s data but not a full pilot. More popular when selling a replacement for an existing product where the buying criteria are more about features and price and less about how it feels to use it.

• 6-stage pipeline: 1. Discovery → 2. Demo → 3. Proposal → 4. Pilot/Trial → 5. Closed Won → 6. Closed Lost. Use if you’re selling software where you have to do both a custom demo and a pilot. Typical with very large enterprise deals where there are a lot of stakeholders and they need a lot of proof points before committing. (Note: if you’re early-stage and in this situation you need to rethink your approach, ideally to break off part of your product into a simpler, faster and cheaper way to land. Long sales cycles are the death of startups).

3. Use loss reasons instead of multiple lost stages

Loss reasons enable you to track your losses without using individual stages for each reason. Combining all your losses into one Closed Lost stage also keeps you honest about your win rate whereas when you use reason-specific stages you tend to cherry pick the denominator and cheat yourself.

You usually have to manually in your CRM. Start with these 7 and make them required whenever a deal is lost:

• No-show: prospect booked a demo but didn’t show and couldn’t be re-booked.

• Not-qualified: discovery call held but prospect was not qualified as ICP size/tech stack/use case. Important to track this so that you can add the relevant criteria to your demo booking form.

• Stopped responding: one or more calls held but prospect is ghosting / non-responsive despite multiple attempts to follow up.

• Timing not right: buyer is not ready to move forward with a purchase and is sticking with their existing solution.

• Feature missing: buyer rejected you due to missing features.

• Price too high: buyer rejected you due to price / budget constraints.

For extra credit create a second field called Loss Reason Detail to capture additional context from the buyer e.g. if you lose and have a debrief call you can use AI to summarize the loss reason and populate the CRM.

Over time, loss reasons become invaluable in finding the gaps in your sales process and re-prospecting to fill the top of your funnel.

4. Close lost your stalled and dead deals

Closing your stalled or dead deals cleans up your pipeline so you can focus on the deals that actually have a shot at closing. It also keeps you honest about if you have enough real pipeline to get to your goals. If you leave them open to pad your pipeline for optics purposes you’re just setting yourself up to fail.

If you find this hard to do, use the following scenarios to get started:

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“Hi, is this David? Do you have a minute? Great, this is Arnie, I’m calling from [company]. We help teams like yours with [problem], so you can [get benefit], using our product that does [description]. Does that sound like something you’d want to learn more about?” — followed by a few discovery questions, a brief product pitch and an ask for a meeting.

While this approach seems logical, all it actually does is overload the prospect with information and give them multiple reasons to say no thanks, not interested or send me the info (aka leave me tf alone). In fact, the pattern that I see is that the more information the rep gives, the fewer meetings they book.

The reality is cold calling is not about selling the product. It’s about selling the next step (usually a meeting), yet most scripts are written to emphasize the former. A different goal requires a different approach.

This post covers:

• Why your BDR’s only goal is a held meeting

• How to pick the right opener based on your prospect’s context

• How to bridge from opener to closing in 2 questions

• What to say in voicemails

Your sole mission is to book the meeting

A BDR/SDR has one job: Get a qualified prospect (i.e. a prospect from a pre-qualified target list) to attend a meeting.

Not a discovery call. Not a mini pitch. Not a qualified opportunity. If the meeting happens, the BDR did their job and the rest is up to the founder or AE who takes that meeting.

This sounds obvious yet very few people write scripts this way. Once you accept that the meeting is the product, half the script falls becomes irrelevant. You stop trying to run discovery with someone you literally just interrupted, you stop trying to get them to imagine what your product looks like (that’s literally what a demo call is for) and you stop trying to create urgency out of thin air.

The script ends up way shorter and shorter scripts book more meetings (just like shorter emails and shorter DMs).

Write your opener based on the prospect’s context

People obsess over openers for good reason: if you fluff your opener its all downhill from there. But there’s no way to wordsmith your way past cramming too much information into the first ten seconds of a call.

Instead, write your opener based on your prospect’s context i.e. where they already are in the process of evaluating you. For example:

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This post covers:

• How to turn a stat into a headline that hooks the reader

• How to use numbers to articulate the problem statement

• How to keep your solution description from boring the reader to death

• Why methodology matters more than product features.

• How to present the results to stand up to scrutiny

• How and where to incorporate customer quotes

How to create a headline that hooks the reader

The title of your case study is crucial because it’s basically the headline that hooks your buyer into reading the rest of it.

A format that works well is “How [customer] achieved [specific result] without [the painful alternative they avoided].”.

The “without” clause is the key. “How Asana cut review time by 60%” is a nice stat, but “How Asana cut review time by 60% without adding headcount” is an intriguing story, because it names the tradeoff the buyer thought was unavoidable. It keeps them reading.

How to articulate the problem statement

The problem statement describes the customer’s pre-transformation state, so you need your buyer to recognize themselves in it. Write it in 3 pieces, each with a stat attached:

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It takes a LOT of planning, handholding and change management — especially in the pilot stage of the sales process — to turn AI interest into AI usage and a signed AI contract. Selling enterprise AI is a MUCH heavier lift than selling traditional SaaS, which is why the deployment strategist role is often the first GTM hire an AI startup needs to make, even before hiring a founders associate, SDR or AE.

This post covers:

• What an AI deployment strategist actually does day-to-day

• What makes it distinct from a traditional CSM or sales engineer

• When to hire them

• Where to source candidates

• What to screen for (interview questions + project)

What an AI deployment strategist actually does

In a nutshell, they own the gap between wanting to try the product and wanting to buy and use the product.

In traditional SaaS, most new products are iterations of incumbents; new enough to spark interest while familiar enough that you can evaluate them sufficiently in a demo call or a self-serve trial. An AE can usually own this end-to-end with minimal support.

AI is totally different. Most products change the entire end user experience so substantially that buyers don’t feel comfortable committing without trying them out first for themselves and herein lies the problem. The more you change a user’s workflow, the more likely they are to get stuck, give up or make a mistake and get frustrated. An AE cannot manage this alone.

The AI deployment strategist owns the outcome of an AI pilot, which in reality means they own 80% of getting the customer to commit (The other 20% is running the procurement gauntlet, which the AE still typically handles).

Day-to-day the pre-sale side of this involves: aligning on use cases, jobs to be done during the pilot, end users to do the evaluation, success criteria, onboarding users individually, tracking adoption, removing blockers, keeping stakeholders engaged, building the ROI story, running the end of pilot readout and asking for the sale.

Day-to-day the post-sale side involves: onboarding additional users, running QBRs, finding expansion opportunities and running renewal conversations — all through a coherent lens of delivering the impact that was promised.

Its not a traditional CSM or sales engineer gig

Most founders make the mistake of starting with a boilerplate SaaS CSM job description, adding AI and pilot experience as nice-to-haves only to wonder why the candidates they attract seem too passive/reactive for what is fundamentally a sales role.

The profile to look for is commercially curious, technically credible, and outcome-oriented. The type of person who doesn’t wait for a customer to raise their hand before taking action. The person that is constantly scanning messy usage data for signals long before problems surface. The individual who can hold their own with a skeptical exec and know how to read the room.

The trigger for hiring is pilot volume, not ARR

You don’t need this role when you’re running one pilot at a time and you’re personally in every conversation with every stakeholder at every touchpoint. You’ll hire someone who has no playbook to inherit and nothing to systematize.

You do need it when you’re routinely running 3+ concurrent pilots, don’t have the bandwidth to give them all your full attention and as a result some convert predictably while others are lost for reasons you can’t quite explain. This inconsistency tells you your results are founder-dependent, and not scalable. Hiring a deployment strategist enables you to extract whatever you are doing intuitively and turn it into a repeatable motion.

Where to source candidates

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Here’s the problem: most CRMs are an unkempt graveyard of deals that have stalled or haven’t been touched in weeks but are still counted, either because they’ve been genuinely forgotten about or because a bigger pipeline looks better than an honest one.

Pointing an LLM at this kind of mess and asking it to tell you the truth is a recipe for disaster, especially when it responds like an over-confident intern and you haven’t got time to fact check it.

This post covers:

• Why messy CRM data breaks your AI insights from the start

• The discipline of closing lost deals instead of pretending they’re still alive

• How your closed lost reasons actually set you up to win later

• A simple way to split your pipeline so it stops lying to you

• Who pipeline hygiene is really for (spoiler: it’s not your manager)

Garbage in, garbage out breaks your AI

Imagine if Claude was trained entirely on fake content, where half the headlines were fabricated and every source was unreliable. You’d get answers that sound authoritative but mean nothing. Your CRM works the same way. If your pipeline isn’t accurate, the insights built on top of it won’t be accurate either. The AI just says it faster and with better formatting.

Close lost your dead deals

One of the highest-leverage habits in CRM hygiene is also the most avoided: closing lost deals.

Founders / sellers leave dead opportunities open for one of three reasons. Either they’ve forgotten about it (common in high velocity inbound), or they haven’t accepted the deal is dead (“I’m following up with them every week!”), or they know closing it lowers their pipeline number. All three reasons are understandable but none of them is acceptable.

You have to close lost your deals. An open pipeline that’s actually 40% dead weight isn’t a pipeline, it’s a wish list. And a wish list pretending to be data will fool any AI model. I’ve yet to see AI tell a founder to close lost a deal. It can’t bring itself to say it.

Oh, and don’t get hung up on the impact to your win rate. There’s no value having a high win rate if you don’t hit your number. You’re just cherry picking and fooling yourself.

Closed lost reasons are where the insight lives

Once you’re in the habit of actually moving deals to closed lost, the next big mistake is treating it as a formality instead of a data source. Closed lost reasons are actually a huge source of insight as they tell you both why your deals are dying at certain stage and give you the springboard for re-engaging in the future.

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Budget approval seldom stalls simply because a number is to large. It usually stalls because the economic case is unclear. A buyer objecting to your price isn’t telling you the price is wrong. They’re telling you they don’t have a model that justifies it.

This post covers:

• Why defending your price loses the negotiation before it starts

• How to pivot from cost to ROI by building a model with your buyer

• How to use the model to reframe the question

• How to deal with pushback on the model

Defending your price is how you lose the negotiation before it starts

When a buyer says your price is too high, your first instinct is to justify the number. You explain your cost structure, your competitive positioning, your team size. None of that matters because your buyer is not asking you to explain the price. They’re asking you to prove it’s worth it.

The moment you start defending the number the entire conversation becomes about whether your price is reasonable in the abstract, instead of whether it makes sense relative to the value you deliver. Don’t justify your number.

Focus on the model inputs, not the price

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An AE who doesn’t understand the customer’s pain, can’t frame ROI, can’t explain what happens in a pilot and doesn’t know how to handle common objections isn’t much use to you. It can even do you more harm than good. They’ll stumble through discovery, lose the room in the demo, and get ghosted by most of their leads.

This post covers:

• Why the first two days are about the customer, not the CRM

• How to build product and competitive fluency before a single live call

• How to teach pricing and ROI so the AE can defend it under pressure

• The role-play framework that turns scripts into instinct

• What certification looks like and why it’s non-negotiable

Days 1 and 2 are about story and customer pains

Before your AE runs a single call, they need to understand who they’re selling to and why those people give a shit.

Day 1 starts with the founder story. Not the pitch deck version, the real one. Why this problem mattered enough to build a company around it, what the early customers looked like, what they were living with before your product existed. Your AE also shadows a disco call, a demo, a proposal call, and a QBR on day one. They need to see the full arc of a deal before they own any piece of it.

Day 2 is the ICP deep dive. Company size, industry, tool stack, use cases, the personas involved in evaluating and what each one cares most about. The AE then reviews five recorded disco and demo calls and shadows the founder live. By end of day 2, they should be able to name the top three ICP pains without notes and map a day-in-the-life of the buyer without your product in it.

Days 3 and 4 are about product mastery and competitive positioning

This is where most founders make their first real mistake. They hand the AE a recorded demo, tell them to “get familiar,” and disappear.

Day 3 is a hands-on product walkthrough with the founder, not a polished pitch. The AE needs room to ask dumb questions and get straight answers. They study the key features and integrations, and they pull together a written list of the top five questions and objections along with how you’ve actually handled them on real calls. By end of day 3, the AE should be able to give a five-minute product walkthrough back to the founder, from memory.

Day 4 moves outward: the market, where you sit in it, and the competitive landscape. Who else plays here, where you win, where you lose, and the language your customers actually use when they refer you. Surface-level “we’re better because” talking points fall flat in a real buyer conversation. The AE needs to know why deals are lost to a competitor and why they’re won.

By end of day 4, the AE should be able to answer “how are you different from [competitor]?” and “how are you different from [legacy provider]?” without hesitating or reaching for a slide.

Day 5 is about pricing and ROI fluency

Pricing is where deals actually die, and it’s the day most onboarding plans treat as an afterthought. Day 5 helps you avoid that.

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I see this a lot. A founder runs a pilot and end users love the product but then the trial period ends with no contract signed. Users ask for a trial extension, the founder happily grants it and suddenly finds themselves in no man’s land with no urgency to get a deal done.

You can’t wing the conversion from pilot to annual contract. You have to engineer it from day one.

This post covers:

• How to structure the four types of calls that turn a pilot into an annual contract

• What to do on each type of call and what to stop doing

• Why the ROI call is a readout, not a pitch, and why that framing matters

Book four types of calls before the pilot starts

Before the pilot kicks off, get 4 types of meetings on your buyer’s calendar:

1. The kick off call

2. One or more end user onboarding calls

3. One or more mid-pilot check-ins, depending on how long your pilot is

4. The ROI decision call

By far and way the simplest and best approach is to set up a weekly recurring meeting and adjust the agenda and attendees based on where you are in the pilot. This matters for three reasons:

1. It signals that this is a structured evaluation, not a free trial with soft boundaries.

2. It’s easier to schedule the ROI call when there’s no conversion pressure yet.

3. If you don’t block the time on your buyer’s calendar you won’t be on their to-do list and your deal will stall.

Use the kick off call to align on goals, success criteria, process and stakeholders

The kickoff call is not a demo. The decision to pilot has already been made. Stop selling and focus on locking in the following:

1. Goals: Why did they start this pilot? Restate the problems, desired impact and critical event that led your buyer to kick off the pilot.

2. Success metrics: How will we know 2 weeks from now that the pilot was successful? Be specific. For example, “We want to reduce time spent on X by Y%” is good whereas a vague statement like, “We want to try using with the product for ourselves” is not a success metric. Don’t just pick one metric, pick a handful. The more metrics you pick, the fuller the picture of success will be.

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Every expansion starts with a conversation. Every conversation starts with a meeting. Every meeting starts with someone getting it on the calendar. As a result, account plans that aren’t meeting-driven are a waste of time. They look like work without producing results and weekly account reviews become circular discussions about what might happen and end with vague next steps.

This isn’t a strategy problem. It’s a process problem. The accounts aren’t growing because nobody is on the customer’s calendar. And if you’re not on their calendar, you’re not on their todo list.

The fix is simpler than most teams expect. It requires one lightweight document per account, one owner per account, and a weekly review that asks exactly one question.

This post covers:

• How to build a three-section account plan in 15 minutes

• How to assign ownership without overcomplicating it

• How to structure a weekly review that drives action, not conversation

The account plan: 3 sections

Most account planning frameworks fail because they’re too heavy. Fifteen-slide decks nobody updates. Spreadsheets with 40 fields. Templates that require a strategy offsite to fill out.

Here’s what actually works: three sections, on one page.

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Their mistakes are remarkably consistent, regardless of what they were selling. If you can avoid these, you’re already ahead of most of your peers. Let’s get into it:

1. Using your investor pitch as your sales pitch

Investors and customers are two completely different audiences with two completely different needs:

Investors are buying the future. They want to know the team, the market size, the trajectory, the vision for what this becomes in five years. They are used to hearing founders use obscure jargon to define a new niche.

Buyers are buying the present. They have a problem today, they have a budget today, and they want to know if your product solves it. They don’t care where you went to college, what your TAM/SAM/SOM is, nor that you are the world’s first at what you do.

When you walk into a sales call with the deck you used to raise your seed round, you’re answering questions nobody asked.

2. Turning your first win into your ICP

You close your first deal. It feels incredible. So you go look for more companies that look exactly like that one — same industry, same size, same persona. Reasonable instinct. Often wrong.

The even more dangerous version: you close three deals across three different segments and decide you have three ICPs. Now you’re chasing fintech, healthcare, and logistics simultaneously with a team of four.

The single biggest cause of GTM slowdowns I see is casting too wide a net too early. When every customer looks different, your messaging never tightens, your demos never sharpen, and your conversations never become predictable. One ICP, one motion, one repeatable story.

3. Cranking up high-volume cold outbound

If you don’t have dozens of similar customers you likely don’t yet know what your target market actually cares about. That alone is reason enough to not waste time on high volume outbound.

Warm intros are always where you start. Not because cold outbound never works — it can — but because asking for intros forces you to build the network that teaches you what these buyers actually care about.

The founders I see ripping through 5,000-contact sequences in month two are usually doing it to avoid the harder work of having ten real conversations with people they had to ask a favor to meet.

Build the network first. The volume play comes later, once you actually have something predictable to scale.

4. Pitching before you’ve done discovery

Discovery is not a formality. It’s the entire game. Before you launch into your pitch, you need three things from the buyer:

1. A pain point that happens often enough that they’re willing to spend money to make it stop. Not a nice-to-have. Not a someday problem. A recurring, expensive headache.

2. A clear understanding of how they’ll measure success. If you both can’t articulate what “this worked” looks like in six months, the deal is going to die before it reaches the finish line.

3. The full cast of characters involved in the decision — champion, blockers, whoever signs the contract. Single-threaded deals get killed by people you’ve never met.

Pitch before you have these and you’re just performing for an audience that hasn’t told you what they want to see.

5. Talking too much on sales calls

You cannot persuade someone to give you money if you don’t know what they’re thinking. You cannot know what they’re thinking if you’re the one doing all the talking.

I’ve reviewed over a thousand founder-led sales calls. The bad ones follow the same shape — the founder talks for 25 of the 30 minutes, the buyer nods and says “interesting” a few times, and the call ends with “let me think about it.” The good ones are the inverse.

Ask a question, shut up, and listen. Then ask another one.

6. Ending a call without booking the next one

People use their calendar as their to-do list, so if you’re not on the calendar, you’re not on the to-do list.

It doesn’t matter how much they loved the demo, how warm the conversation felt, or how senior they were. No next meeting booked = the deal is already cooling.

Book the next step before you hang up. Every call. Every stage of the process. No exceptions.

7. Fumbling pricing

Pricing is where I see otherwise-confident founders fall apart - e.g:

• Delaying the conversation — “let’s circle back on pricing next time”

• Deferring entirely — “what’s your budget?”

• Negotiating against yourself before the buyer has even pushed back — “it’s $50k, but we have flexibility, and honestly we can probably work something out”

State the price. Ask how it sounds. Shut up. Let them respond. Whatever happens next is information, not a verdict.

8. Confusing product access with a pilot

A pilot has a defined success criteria, a defined timeline, a champion driving usage, and a clear path to an annual contract if it works. Giving someone a login and hoping they figure it out is not a pilot. It’s a free trial.

When you leave buyers to evaluate the product on their own, you’re rolling the dice that they’ll log in unprompted, navigate to the right feature, have the exact use case in front of them, and find it so irresistible they come back asking to pay you. That almost never happens. They get busy, they forget, they churn out before you ever had a real shot.

Run actual pilots. Define what success looks like. Stay in the deal.

9. Negotiating over email

Email gives you words. It doesn’t give you reactions.

When you send a price over email, you have no idea if the buyer winced, shrugged, or smiled. You don’t know if they think it’s a bargain or a robbery. You’re flying blind into the most important conversation of the deal.

Pricing and negotiation happen live. Always. Get on a call, watch their face, listen to the pause before they respond. That’s the data you need to know where you actually stand.

10. Hiring an AE prematurely

Here’s the test: never hire an AE unless you are confident you can get them to quota with a predictable lead generation and closing process you’ve already built.

If you can’t consistently close deals yourself, an AE isn’t going to figure it out for you. They’re going to flounder, blame the product, blame the leads, miss quota, and you’ll be back in the seat in nine months — except now you’ve also burned $250k and wasted half your runway.

Your first GTM hire is almost always a deployment strategist or a founder’s associate — someone who absorbs the repetitive parts of the motion you’ve already figured out, so you can keep selling and keep learning. The AE comes after the playbook exists, not before.

If any of these sound familiar to you, talk to me about sales coaching. We’ll talk about where you are currently stuck, what a typical coaching engagement looks like and if its a good fit for you.

GTM trends for AI startups

• 4 GTM trends for AI startups to watch in 2026 — customer success as a pre-sales function, demonstrating tangible ROI, early-stage brand building, GEO

Sales Management

• How to survive your first year as a sales manager — mistakes to avoid, skills to learn, processes to build.

• How to build a sales training program that actually sticks — less theory, more practice.

• How to stop your AEs from negotiating against themselves — a discounting framework for early-stage teams.

• How to ramp your first SDR in 10 days — day-by-day guide to get them booking meetings by their third week.

Closing Enterprise Deals

• How to justify the ROI of your AI product — build a simple business case.

• How to respond to an RFP — a step-by-step system for winning competitive bids.

• How to manage scope creep without saying no — no need to be the bad cop, just ask better questions.

• How to structure enterprise pricing when buyers are scared to commit — a two-tier license structure, rollout plan template and how to frame it.

Generating Leads

• 7 outreach campaigns to try before resorting to cold email — segment prospects by psychological state and meet them where they already are.

• How to show up in AI answers — 9 AI-specific tactics and how to implement them.

• How to make an immediate impact as the first marketer in a startup — by starting at the bottom of the funnel and working your way up.

• How to write a startup homepage that converts — don’t leave them wondering WTF your business does.

Crushing Procurement

• How to close enterprise deals while your SOC2 is still in progress — by keeping it boring and procedural.

• How to get your sales contract through legal — a salesperson’s guide

• How to get through procurement — spot their lies, tricks and tactics.

An SDR who doesn’t understand the customer’s pain, the competitive landscape, or your company’s voice will make calls that go nowhere, turn off your best leads and lose confidence faster than you can coach it back.

This post covers:

• Why the first two days are the most important of the entire ramp

• How to build product fluency before touching a single sequence

• The role-play framework that makes the training stick

• What certification looks like and why it matters

• A downloadable training plan

Days 1 and 2: Story and customer truth before everything else

Before your new SDR touches a sequence, a dialer, or a CRM field, they need to understand who they’re calling and why those people care. That’s what the first two days are focused on.

Day 1 starts with the founder story. Not the company overview deck. The actual story: why this problem mattered, what the early customers looked like, what pain they were living with before your product existed. Your SDR also shadows live customer calls, where they can hear tone, hesitation, and the moments when a prospect leans in.

Day 2 is all about the ICP. The SDR reads customer win stories and maps a realistic day-in-the-life of your target persona. What does their morning look like? What are they accountable for? What makes their quarter go sideways?

By end of Day 2, your SDR should be able to articulate the top three ICP pains from memory, out loud, without looking at a slide. If they can’t do that, they’re not ready for Day 3.

Days 3 and 4: Develop product and market fluency

This is where founders make the second-biggest mistake of the ramp: handing the SDR a recorded demo and disappearing.

The founder needs to walk the SDR through the product hands-on. Not a polished pitch. A real walkthrough where the SDR can ask dumb questions and get honest answers. They also need to study your two or three sharpest differentiators and go deep on competitors. Not surface-level “we’re better because” talking points. Real understanding of where competitors win, where they lose, and why buyers switch.

By end of Day 4, the SDR delivers a five-minute product demo without notes. They also have to answer “how are you different from [competitor]/[legacy]?” with confidence and conviction based on what they learned.

If the demo is shaky, run it again. Don’t move on.

Days 5 and 6: Master outreach mechanics

Now your SDR is ready to look at sequences, calls, and the CRM.

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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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