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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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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