1. Sharp POV
3. Discovery
How to win

April Dunford
Author, Obviously Awesome
First-call positioning deck
How to win
In this chapter, we dive into why we believe if you know what you're uniquely good at, and can make the buyer care about it in the first five minutes, the rest of the deal is yours to win.
This chapter was written in collaboration with April Dunford. April is the leading expert in crafting sales pitches. She spent twenty five years as a B2B VP of Marketing, twelve more as a positioning consultant, and wrote Obviously Awesome and Sales Pitch to help more B2B companies nail their positioning and sales pitch. This chapter only captures a slice of her work. If you want to learn more from April, follow her on Linkedin or at aprildunford.com
To understand what makes a successful first sales call, we first have to understand how the buyer and the seller are approaching the conversation.
By the time a buyer gets to the first call, they've built a shortlist without you and formed early opinions about which vendors look credible. They arrive with mountains of information from your website, comparison pages, peer recommendations, community threads, and whatever their AI assistant told them. They may think they want a product tour. What they actually need is the buying criteria: insight into which of those facts matter and how to make a good decision in your category.
The seller, on the other hand, arrives wanting information from the buyer: budget, timeline, who signs off, what they use today, and whether this is a deal worth pursuing. In return, they assume the buyer wants information about the product.
With that in mind, it's the seller's job to act as a guide to the market they're in: to show them how the category works, which differences actually matter, and which ones are noise. Done well, this earns the most valuable piece of the seller's job: trust.
This approach carries well beyond the first call. A buyer who accepts your view of the market carries it into every conversation that follows, and, if done successfully, ends up judging every other vendor against the criteria you helped them set.
The rest of this chapter shows how to do that, so the buyer leaves seeing the market through your lens, understanding why your product is built the way it is, and carrying a story simple enough to repeat internally when you're not in the room.
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Tactics
Tactics
Contrary to other sales methodologies that teach openers, how to ask good questions, etc., we believe the success of the call is built on the back of how clear your product's positioning is. That said, let's see what good positioning looks like then dive into how the call unfolds around it.
Step 1. How to create differentiated positioning
Positioning is how your product is different and better than the alternatives for a particular set of customers. Said differently, it's what you're the best in the world at delivering for a well-defined group of customers who care a lot about it. Positioning works like context setting: it tells buyers what your product is, what to compare it to, and why it matters. It isn't messaging or a tagline. It's the foundation underneath them, and the starting point for your messaging, branding, lead generation, sales strategy, and pitch.
There are five things you need to answer in a positioning exercise:
Component | The question it answers |
|---|---|
Competitive alternatives | If we did not exist at all, what would this customer do instead? |
Differentiated capabilities | What do we have that none of those alternatives have? |
Differentiated value | Why does that capability matter to the customer, in terms they care about? |
Customers who care a lot | Who cares about that value far more than everyone else does? |
Market category | What context makes that value obvious to a buyer straight away? |
Start with the customers who already love you
Pull a list of your ten to twenty best customers. Select ones who bought fastest, use the product most, renew year over year, and refer you to peers. Then get on a short call with whoever drove the purchase at five or six of them. Ask what they were using before they found you, and what they would do tomorrow if you disappeared.
Here are a few sample questions to ask to get to you the input you'll need:
Who else they looked at and what nearly stopped them from buying?
What would they tell a peer you're good at?
What has changed in their business since they started?
Listen for the specific words they use. The patterns across those calls will give you a starting point.
Do it as a team
Positioning works best as a cross-functional effort between company leadership, sales, marketing, product, and customer success. Each represents a different side of the business and sees a different slice of the value customers get. Sales hears what wins and loses deals, customer success sees why people stay, product knows what's genuinely hard to copy, and leadership can make the call when those views pull in different directions. bring those sides of the business together to get a holistic picture of the value you provide to them and what won them over.
Work through the components in order
Start with competitive alternatives: what your best customers would do if you didn't exist. That list often includes the status quo or doing it manually, and it helps to group the alternatives together.
Next, isolate what you have that those alternatives don't. For each of those unique attributes, ask "so what?" to capture the value it enables for customers, then group that value into themes. Keep asking until you reach something specific a customer cares about, but stop before you land on something generic like saving money, which any competitor can claim.
From there, identify who cares a lot about that value, and only then choose a market category.
Choose the category
Write down two or three candidate categories and test each one against your value themes. A good pulse check is asking yourself: Would a buyer who hears this category immediately assume the strengths you actually have?
In most cases, there three options. You can:
Compete head-to-head as the leader of an existing category
Win a sub-segment of an existing category where your strengths matter most
Create a new category
Creating a category is the hardest path, so default to the sub-segment unless no existing category makes your value obvious.
Write it down so others can use it
Capture the result on a single page: the alternatives, your differentiated capabilities, the value themes with proof for each, the best-fit customer profile, and the category. April calls this a positioning canvas. Share it with sales and marketing, use it to rebuild the pitch and website copy, and revisit it whenever the market shifts or you start losing deals you used to win.
Step 2. Define your unique market insight
The insight is a statement about the market that the buyer has to believe in order for your value to matter to them. It is important to understand that the insight is not a description of the buyer's problem. It is a claim about the world that makes your strengths the deciding factor.
To find it, you must start from your differentiated value, then ask what a person would need to believe for that value to be the most important consideration in the evaluation.
Here's a simple example. Imagine two database companies whose products are almost identical, except for one thing.
Database A | Database B | |
|---|---|---|
Speed | Same | Same |
Scale | Same | Same |
Price | Same | Same |
Flexibility | Compatible with only same-company products | Plug in any tool you want |
Setup | All-in-one, fast, one vendor to call | Takes a bit more work |
If Database B opens the call by talking about speed or scale, the buyer learns nothing, because the two products are even on both. So instead, B's seller asks a few simple questions:
Q: "Why are you storing all this data?"
A: "Because it's becoming one of the company's most valuable assets."
Q: "What will you do with it?"
A: "Run analytics and AI on top of it."
Q: "Which tools, specifically?"
A: "Nobody knows yet, because we haven't worked through the use cases"
In this scenario, the buyer reaches the conclusion that a database you'll keep for years has to stay open to whatever comes next. Openness becomes the deciding factor, and it's the one thing Database B is guaranteed to win on.
Notice what was left out of the opening: features, technical specs, and proof points. All of that comes later in the call. The opening has one job, which is to establish the single criterion that your company wins on.
Step 3. Lay the call out in eight steps
Think about the call in two halves.
The setup: the goal is to align the buyer to your view of the market. We covered this in the section above.
The follow through: proof that you deliver on your unique value outlined in the setup.
If you deliver all eight steps without the buyer talking, the structure has failed even if you said every word correctly.
Here is the sequence at a glance, followed by what belongs on each step and what does not.
Step | Goal |
|---|---|
1. Insight | Establish your view of the market and the one thing the buyer has to believe for your value to matter. |
2. Alternatives | Map the buyer's options into a few approaches, with an honest account of each. |
3. Perfect world | Get the buyer to agree out loud on what any good solution needs to do. |
4. Introduction | Introduce who you are through the market category you belong to. |
5. Differentiated value | Demonstrate the two or three things you're exceptional at. |
6. Proof | Prove you deliver on what you just claimed. |
7. Objections | Address the concerns that commonly kill deals before the buyer raises them. (Optional.) |
8. The ask | Agree on a specific next step with the buyer. |
We'll use the same two database companies through each step to demonstrate how this works in practice.
As a reminder:
Database A's strength is that everything comes bundled together, which makes it fast and cheap to set up, with one vendor to call.
Database B's strength is openness: customers can run whatever tools they want on top of it.
Insight
The insight is your point of view on how the market works, boiled down to the one idea the buyer has to believe for your strengths to matter. To find yours, ask what a customer needs to understand in order to see why your differentiated value is important.
On the call:
Deliver it as a short conversation, not a slide, and keep it to a few minutes.
Make a claim about the market the buyer can agree or disagree with, then give just enough reasoning for them to reach the conclusion themselves.
Check in before moving on. Ask something like, "Does that match what you're seeing?" If they push back, stay here until you agree, because it is the backbone of everything that follows.
Example: Neither database can win on speed or scale, since the two products are even on both, so the insight is about time. The data a company stores today will outlive every tool it runs on top, and the analytics and AI tools it will want in a few years haven't been invented yet. Database B's seller gets there with three simple questions:
Why are you storing this data?
What will you do with it?
Which tools will be using this data?
Once the buyer admits nobody knows yet, openness becomes the thing that decides the purchase.
Alternatives
This step maps the market for the buyer, including the parts of it you don't sell. Laying out every realistic option is what makes you a guide to the category rather than one more vendor arguing for itself.
On the call:
Cover everything the buyer could genuinely do. Those options include the status quo, doing it manually, building in-house, an adjacent category of tool, or doing nothing.
Group the options into roughly three approaches and give each one a fair account, strengths included.
Use it for discovery. On the call, ask what they use today, what they've tried, who else they're evaluating, and what constraints they're working under.
Example: Database B's seller lays out three options.
An all-in-one package like Database A is fast, cheap up front, and easy to support, but the vendor decides what you can add later.
An open option like Database B takes a bit more work up front but keeps future choices available.
Keeping the current database costs nothing today but won't handle the analytics and AI work the buyer is planning.
Perfect world
Before you say anything about your product, describe what an ideal solution would need to do, and ask the buyer whether they agree. The requirements should follow directly from your insight and be written around your differentiated capabilities.
On the call:
Ask for agreement: "Would you agree that any real solution here would need to do these three things?"
If they agree, you've set the criteria your product happens to meet.
If they disagree, either your setup didn't land or they want something you don't do. Better to find out now than two months into a deal.
Example: Any database you plan to keep for years would need to run tools that don't exist yet, add them without forcing a migration, and do it without one vendor deciding on your behalf what's supported. A buyer who agrees to those three requirements has agreed to openness, and Database B still hasn't been mentioned.
Introduction
Only now do you say who you are, and you say it through your market category. The right category makes your strengths look obvious and your gaps look irrelevant.
On the call:
Name the category you've chosen.
Add one line about who you serve.
Keep it short. The buyer has already agreed to the criteria, so show where you fit rather than pitching.
Example: If Company B introduces itself as just another database, the buyer compares it on speed and price, where it's even with Database A. If it introduces itself as an open data platform, the buyer compares it on flexibility, the exact criterion they just agreed matters most. The product hasn't changed but the category that it operates in has.
Differentiated value
This is where you show the two or three things you're exceptional at, and connect each one directly to a requirement the buyer agreed to in the perfect-world step.
On the call:
Lead with your biggest value theme.
Name the value first, then show the part of the product that delivers it.
Stick to two or three themes.
Example: Company B's seller leads with flexibility, tying it back to the buyer's own words: they need to add tools that don't exist yet without a migration. Then she shows how a new analytics tool plugs into B.
Proof
This is the closing argument of the call. You've made claims, and now you show evidence that you deliver on them.
On the call:
Use named customer outcomes, hard numbers, and benchmarks.
Match the proof to the buyer's industry. In April's view, this is the one place in the first call where tailoring belongs.
Example: For a retail buyer, Company B's seller shares how another retailer added a new AI forecasting tool shortly after it launched, without migrating any data.
The ask
Close the call with a next step that both sides have agreed to.
On the call:
Agree on one specific next step.
Name who needs to be there.
Put a time on the calendar.
How to win
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Common mistakes
Common Mistakes
1 Features, features, features
We've all had a sales call where the rep shares their screen, opens the product, and walks through it one screen at a time, explaining what each part does. Pricing shows up on a slide near the end. It feels thorough, but it hands the hard work of translating every feature into something that matters to their business, and work out how you're different from the five other vendors who gave them the same tour last week.
The fix is to hold the product back and follow the steps outlined in the last section. Open with your insight, map the alternatives, and agree on what a good solution needs to do before anyone sees a screen. When the product finally appears, show only the parts that deliver the two or three things you're exceptional at, and tie each one to a requirement the buyer has already agreed to.
2 The founder origin story
Plenty of calls open with how the company came to exist: the founder hit a problem, couldn't find anything on the market that solved it, and built it themselves. The story is usually true, which is what makes it so tempting. But it rarely works in a first call. It's too complicated to tell well in the few minutes you have, it loses its spark when a rep who wasn't there tells it secondhand, and it never says who the product isn't right for, so the wrong buyers have no way to rule themselves out early.
The fix is to swap the origin story for your insight. The founder's story often contains it, because whatever the founder noticed about the market is the seed of your point of view. Pull that observation out and state it as a claim about the market that any rep can deliver.
3 Letting the buyer run the call
Many buyers come into calls thinking they know what they want. They say they need a data lake with four specific capabilities. The rep writes all four down and promises to come back with answers on each. At no point does anyone ask whether a data lake is the right answer to the problem underneath the request.
That list came from somewhere, and often it came from a competitor who already ran the kind of call this chapter describes and taught the buyer which criteria matter. So you spend the call answering a test someone else wrote. Even if you ace it, the buyer leaves knowing you can do four things they asked about, and still not knowing what you're exceptional at or why anyone picks you over the alternatives.
The fix is to step back before answering. Ask where the requirements came from and what problem sits underneath them, then walk through your insight and the alternatives so the buyer can see the market through your lens. If their criteria still hold up, you've lost nothing. If they don't, you've just rewritten the test.
Tactics
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How to avoid AI slop
How to avoid AI slop
Don't ask a model for your insight or differentiated value
Both your insight and differentiated value come from asking real customers what they would have done if you did not exist, and from an internal argument about which of your capabilities can actually be proven. A model trained on the public web gives you the consensus language of your category, which is likely the language your competitors are already using.
Don't generate an entirely different pitch for every first call
This is the easiest thing to do and the most tempting, because the output looks personalized and reads well. However, a good pitch lands regardless of the buyer. Instead of personalizing the pitch, use AI to gather information on if this buyer show signs of believing your insight, or signs that they will resist it. Agreement means you move faster through the setup. Resistance means you spend longer there. The insight itself stays fixed either way.
Common mistakes
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4. Champion Enablement

April Dunford
Author, Obviously Awesome
1
1
Chapter overview:
3. Discovery
How to win
Tactics
Common mistakes
How to avoid AI slop
1. Sharp POV
2. Outbound & cold call
3. Discovery
4. Champion Enablement
5. Business Case
6. Demo
7. Mutual Action Plan
9. Pilot
10. Procurement, Security, and Legal
4. Champion Enablement
Chapter overview:
3. Discovery
How to win
Tactics
Common mistakes
How to avoid AI slop









