Obviously Awesome: How to Nail Product Positioning so Customers Get It, Buy It, Love It
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Authors: April Dunford Tags: product management, marketing, startups, strategy Publication Year: 2019
Overview
I wrote this book because I saw too many great products fail for a simple, yet devastating, reason: customers didn’t understand them. You can have the most innovative, powerful product in the world, but if its value isn’t immediately obvious, you’re dead in the water. This isn’t just a marketing or sales problem; it’s a fundamental business problem that starts with weak [[product positioning]]. For years, I’ve seen founders, marketers, and product leaders struggle with this. They either stick with a ‘default’ position that undersells their strengths, or they try to use outdated tools like the fill-in-the-blanks positioning statement, which is like trying to perform surgery with a butter knife. It just doesn’t work. ‘Obviously Awesome’ is my answer to that. It’s not a book of abstract theories; it’s a practical, step-by-step playbook that I’ve developed and refined over two decades of launching and repositioning products. I break positioning down into its fundamental components and give you a 10-step process to deliberately assemble them in a way that makes your product’s unique value crystal clear to the customers who will care the most. This book is for anyone in a startup or tech company—founders, executives, marketers, salespeople—who needs to connect their product with prospects to shorten sales cycles, increase revenue, and build a base of passionate fans. In today’s crowded markets, you can’t afford to be misunderstood. My goal is to give you a repeatable methodology to ensure your product is perceived as ‘obviously awesome’.
Book Distillation
1. Positioning as Context
Positioning is the act of deliberately setting the context for your product. Just like the opening scene of a movie, it gives customers the essential clues to understand what your product is, who it’s for, and why they should care. Without this context, even a world-class product can fail because its value isn’t recognized. Customers will create their own context for you if you don’t provide one, and their assumptions will almost certainly put you at a disadvantage. We often fall into traps by either being stuck on what we intended to build, not what the product has become, or by failing to see that the market itself has changed around our product.
Key Quote/Concept:
The Two Traps of Positioning. Trap 1: You are stuck on the idea of what you intended to build, and you don’t realize that your product has become something else (e.g., you think you built a ‘cake,’ but it’s really a ‘muffin’). Trap 2: You carefully designed your product for a market, but that market has changed (e.g., your ‘diet muffin’ is now competing with ‘gluten-free paleo snacks’).
2. The Five (plus One) Components of Effective Positioning
The traditional positioning statement is a trap because it assumes you already know the answers. A better approach is to build your positioning from the ground up using its core components. There are five essential, interconnected pieces: Competitive Alternatives, Unique Attributes, Value (and proof), Target Market Characteristics, and Market Category. A sixth, optional component is Relevant Trends. The key is that these components are interdependent and must be worked through in a specific order to construct a position that is strong, defensible, and resonates with customers.
Key Quote/Concept:
The Five (Plus One) Components. 1. Competitive alternatives (what customers would do if you didn’t exist). 2. Unique attributes (your features/capabilities that alternatives lack). 3. Value (the benefit those attributes deliver). 4. Target market characteristics (the people who care most about that value). 5. Market category (the frame of reference for customers). 6. (Bonus) Relevant trends (why your product is important now).
3. Step 1: Understand the Customers Who Love Your Product
The entire positioning process hinges on a single starting point: your best-fit customers. Don’t look at your entire customer base or, worse, the market as a whole. Focus only on the ecstatic fans who bought quickly, understood the value immediately, and advocate for you. These customers hold the key to understanding your true, differentiated value. Their perspective provides the anchor for every subsequent step in the process. If you don’t have any super-happy customers yet, your job is to find them, not to lock in your positioning.
Key Quote/Concept:
Best-Fit Customers. These are the customers who buy quickly, rarely ask for discounts, and tell their friends about your offerings. They are your reference point for the entire positioning exercise.
4. Step 2 & 3: Form a Team and Let Go of Baggage
Positioning is a core business strategy, not just a marketing task. The process must be a team effort driven by the business leader (CEO/founder) and include a cross-functional group from sales, marketing, product, and customer success. Before you begin, the team must consciously agree to set aside its ‘[[positioning baggage]]’—the ingrained, internal story of the product’s history and original intent. You must learn to see the product as a new customer does: a blank slate, free from your history and assumptions.
Key Quote/Concept:
[[Positioning Baggage]]. This is the disconnect between how product creators see the product (with its full history) and how customers first perceive it. Market confusion starts here. You must let this baggage go to see the product through a customer’s eyes.
5. Step 4, 5, 6 & 7: Deconstruct Your Positioning
This is the core of the work. First, list the true competitive alternatives from your best customers’ perspective (often ‘spreadsheets’ or ‘doing nothing’). Second, based on those alternatives, isolate your unique, provable attributes. Third, translate those attributes into the value they deliver for customers, grouping them into 1-4 value ‘themes’. Finally, define the characteristics of a target segment that cares deeply about that specific value. This sequence—from competitor to feature to value to customer—is critical.
Key Quote/Concept:
Features -> Benefits -> Value. A feature (‘15-megapixel camera’) enables a benefit (‘sharper images’), which delivers value (‘photos that are sharp even when printed or zoomed in’). You must articulate the value in the customer’s context.
6. Step 8: Find a Market Frame of Reference and Determine How to Position in It
Now, choose a market category that makes your unique value obvious to your target segment. This category is a frame of reference that triggers powerful assumptions. You can choose one of three styles to compete: Head to Head (aiming to be the leader in an existing market), Big Fish, Small Pond (dominating a subsegment of an existing market), or Create a New Game (inventing a new market category from scratch). Your choice depends on your product’s strengths and the maturity of the market.
Key Quote/Concept:
Three Positioning Styles. 1. Head to Head: Win an existing market. 2. Big Fish, Small Pond: Win a subsegment of an existing market (e.g., ‘CRM for Investment Banks’). This is often the best strategy for startups. 3. Create a New Game: Invent a new market (e.g., ‘Marketing Automation’). This is the most difficult but can have massive rewards.
7. Step 9 & 10: Layer on a Trend and Capture Your Work
Optionally, you can layer a relevant trend (like [[AI]] or [[DevOps]]) on top of your positioning to create urgency and make your product more interesting right now. Be careful: the trend must have a clear, logical link to your product and its value, otherwise you will just create confusion. Finally, capture your completed positioning in a shareable document, like a positioning canvas. This ensures the entire organization has a common foundation for [[messaging]], sales, and [[product roadmap]] decisions.
Key Quote/Concept:
The Positioning Canvas. A one-page document that captures the key components: Competitive Alternatives, Unique Attributes, Value, and Target Segment (‘Who Cares a Lot’), all under the umbrella of a chosen Market Category. This makes the positioning easy to share and use.
8. After Positioning: What Happens Next?
A defined positioning is not the end goal; it’s the start. The immediate next step is to translate it into a compelling [[sales story]]. This narrative defines the problem, highlights the flaws in current approaches, describes a ‘perfect world,’ and then introduces your product as the key to achieving it. This story becomes the backbone of your sales deck, your website messaging, and your marketing campaigns. Over time, your positioning will also guide your [[product roadmap]] and [[pricing]] strategy, making it a true business-wide strategic compass.
Key Quote/Concept:
The Sales Story Arc. A narrative structure that flows from Problem -> Current Solutions -> The ‘Perfect World’ -> Your Product Introduction -> Value Themes. This translates your abstract positioning into a concrete pitch that your sales and marketing teams can execute.
Generated using Google GenAI
Essential Questions
1. Why is ‘default’ positioning so dangerous, and how does the book’s methodology provide a deliberate alternative?
Default positioning is dangerous because it’s based on unconscious assumptions, often stemming from the product’s origin story rather than its current reality. I argue that teams fall into two traps: they’re stuck on what they intended to build, not what the product has become (the ‘cake’ that’s actually a ‘muffin’), or the market has changed around them, making their initial positioning obsolete. This leads to what I call [[positioning baggage]], where internal views clash with external perceptions, creating market confusion, long sales cycles, and high churn. My methodology offers a deliberate alternative by breaking positioning down into its core components and reassembling them from a customer-centric viewpoint. The 10-step process forces a team to let go of baggage and start with the only opinion that matters: that of their best-fit customers. By systematically analyzing competitive alternatives, unique attributes, value, and target segments, a team can construct a market frame of reference that makes their strengths obvious, rather than simply defaulting to the category they started in. This transforms positioning from a passive assumption into an active, strategic choice that aligns the entire business.
2. What are the five core components of effective positioning, and why is the order in which they are addressed so critical?
The five core components of effective positioning are: 1. Competitive Alternatives, 2. Unique Attributes, 3. Value (and proof), 4. Target Market Characteristics, and 5. Market Category. I also include a sixth, optional component: Relevant Trends. The order is critical because each component logically flows from the previous one, creating a chain of reasoning that builds a solid foundation. It all starts with understanding the customer’s perspective: what would they use if your product didn’t exist? This list of [[Competitive Alternatives]] defines the context for comparison. Only then can you identify your [[Unique Attributes]]—the features you have that the alternatives lack. These attributes, in turn, enable specific [[Value]] for the customer. Once you understand that unique value, you can identify the [[Target Market Characteristics]] of the people who care most about it. Finally, with a clear understanding of your value and your target audience, you can choose a [[Market Category]] that best frames that value and makes it immediately obvious. Starting out of order, for instance by defining features in a vacuum or picking a market category first, leads to positioning that doesn’t resonate because it’s not anchored in the customer’s reality.
3. How does the concept of ‘best-fit customers’ serve as the anchor for the entire positioning process?
The concept of ‘best-fit customers’ is the essential starting point and anchor for my entire positioning methodology. These are not just any customers; they are the ecstatic fans who ‘get’ your product immediately, buy quickly without demanding discounts, and become advocates. I insist on starting here because these customers hold the key to your true, differentiated value. Their perspective cuts through the noise of your broader, more heterogeneous user base, which might include moderately happy or even unhappy customers who use the product for unintended reasons. By focusing on this core group, you can reverse-engineer your success. They implicitly understand your best positioning because they are living it. Their view of competitive alternatives is the most relevant one, their favorite features are your most valuable unique attributes, and the problems they solve are the clearest expression of your value. Without this anchor, the positioning process becomes a circular, theoretical exercise based on internal assumptions. By starting with your happiest customers, you ground the entire 10-step process in proven, real-world market traction, ensuring the resulting positioning is not just a guess, but a reflection of what already works best.
Key Takeaways
1. Positioning is the Act of Setting Context
My central argument is that positioning is not about messaging, taglines, or even the features themselves. It is the deliberate act of setting the context for your product so that customers can figure out what it is, who it’s for, and why they should care. Like the opening scene of a movie, good positioning provides a frame of reference that triggers a set of powerful assumptions about competitors, price, and capabilities. If you don’t deliberately set this context, customers will do it for you, and they will almost certainly choose a context that puts your product at a disadvantage. The book demonstrates this with the vignette of the world-class violinist Joshua Bell playing in a subway station; the product (his music) was exceptional, but the context (a street performer) made its value invisible. This is why the choice of [[Market Category]] is one ofthe most crucial steps in the positioning process—it’s the primary tool for setting context.
Practical Application: An AI product engineer building a new code generation tool must decide its context. Is it ‘AI-powered code completion’ (competing with GitHub Copilot), a ‘developer productivity platform’ (competing with a broader suite of tools), or a ‘legacy system modernization tool’ (a niche with different buyers and value)? Choosing the context of ‘code completion’ sets specific expectations about features and integration. Choosing ‘modernization tool’ frames the value around cost savings and risk reduction, attracting enterprise buyers. The context defines the game you’re playing.
2. Your Positioning Is Hidden Inside Your Happiest Customers
One of the most significant and actionable ideas in the book is that the answers to your positioning questions are not found in brainstorming sessions or by analyzing the entire market. They are found by studying your ‘best-fit customers.’ These are the customers who are already successful and delighted with your product. They represent a segment where your value is already ‘obviously awesome.’ The entire 10-step process is designed to extract their implicit understanding and make it explicit. By identifying this group first, you create a lens through which to view every other component. What do they see as alternatives? What features do they value most? What are their defining characteristics? This approach de-risks the positioning process by grounding it in what has already been proven to work, rather than speculating about what might work in the future for a theoretical audience. It shifts the goal from inventing a position to discovering the one that already resonates most strongly.
Practical Application: An AI product team has a product with mixed adoption. Instead of surveying all users, they should interview the 10-15 users with the highest engagement and retention. These ‘best-fit’ users might reveal they aren’t using the AI for its ‘smart search’ feature as intended, but as a way to automatically generate compliance reports. This insight anchors a repositioning effort: the competitive alternative isn’t other search tools, but manual report-building. The unique value is automated compliance, and the target market is regulated industries. This discovery, found in happy customers, can pivot the entire [[product roadmap]].
3. Positioning Is a Company-Wide Strategic Compass
I stress that positioning is not a siloed marketing exercise; it is a foundational business strategy that impacts every department. A positioning exercise that isn’t led by the CEO or business leader and doesn’t include cross-functional input from sales, product, and customer success is doomed to fail. The output of the process—the [[Positioning Canvas]]—is not just for creating a new homepage. It informs the [[product roadmap]] (what features reinforce our unique value?), the sales strategy (what is our sales story and who do we target?), and even pricing (what are the price expectations in our chosen market category?). When my startup repositioned from a ‘database’ to a ‘data warehouse,’ it didn’t just change our pitch; it changed our roadmap, our pricing, and how we saw ourselves. This holistic view elevates positioning from a tactical task to a critical component of the company’s core strategy for winning a market.
Practical Application: An AI company’s new positioning as a ‘Big Fish, Small Pond’ player—’AI for Hedge Fund Analysts’—must be reflected across the company. The product team must prioritize features for financial data analysis over general-purpose ones. The sales team needs a new story focused on alpha generation, not just ‘smarter insights.’ The marketing team must target financial publications, not broad tech blogs. The CEO must use this positioning to explain the company’s focused strategy to investors. A change in positioning requires a change in company-wide execution.
Suggested Deep Dive
Chapter: Step 8: Find a Market Frame of Reference That Puts Your Strengths at the Center and Determine How to Position in It
Reason: This chapter is the strategic climax of the 10-step process. After deconstructing your product’s value from the customer’s perspective, this is where you make the pivotal decision about which ‘game’ to play. My breakdown of the three positioning styles—Head to Head, Big Fish, Small Pond, and Create a New Game—provides a clear, strategic framework for this choice. For an AI product engineer, this is especially critical. AI products are often novel and can be framed in multiple ways. This chapter provides the mental models to decide whether to take on an incumbent directly, carve out a defensible niche (often the smartest move for a startup), or attempt the difficult but rewarding path of category creation. The stories of Wattpad and my own startup’s transformation from a database to a data warehouse provide concrete examples of this thinking in action.
Key Vignette
From a Crummy Database to a Kickass Data Warehouse
Early in my career, I worked at a startup with a special kind of database that was exceptionally fast at analysis on large datasets. We positioned ourselves as a ‘database,’ which put us in direct competition with the market leader, Oracle. Prospects immediately asked how we were better than Oracle, and the honest answer was that we weren’t a better general-purpose database; we lacked many of their features. After a customer told us we seemed more like a ‘data warehouse,’ we had a breakthrough. We repositioned the company into the data warehouse market—a category where our strength in analytics was the most important feature and our weaknesses were irrelevant. We went from being a ‘cheaper, crappier Siebel’ to a leader in a different, better-fitting market, which ultimately led to a massive acquisition.
Memorable Quotes
Positioning is the act of deliberately defining how you are the best at something that a defined market cares a lot about.
— Page 17, Introduction
Even a world-class product, poorly positioned, can fail.
— Page 29, I. WHAT IS POSITIONING? - Positioning as Context
The worst part of a positioning statement exercise is that it assumes you know the answers.
— Page 45, I. WHAT IS POSITIONING? - The Five (plus One) Components of Effective Positioning
Your best-fit customers hold the key to understanding what your product is.
— Page 62, II. THE 10-STEP POSITIONING PROCESS - Step 1. Understand the Customers Who Love Your Product
Category creation is about selling the market on the problem first, rather than on your solution.
— Page 117, II. THE 10-STEP POSITIONING PROCESS - Step 8. Find a Market Frame of Reference…
Comparative Analysis
My book, ‘Obviously Awesome,’ stands on the shoulders of giants like Al Ries and Jack Trout’s ‘Positioning: The Battle for Your Mind,’ but it takes a fundamentally different approach. While Ries and Trout brilliantly defined what positioning is and why it’s important, their work was largely conceptual, leaving many to wonder how to actually do it. My book is the answer to ‘how.’ It’s a step-by-step, operational playbook, not a collection of theories. Similarly, Geoffrey Moore’s ‘Crossing the Chasm’ is essential reading for tech marketers, but it focuses on the specific challenge of moving from early adopters to the mainstream market. My methodology is a prerequisite to that; it helps you nail the foundational positioning you need before you can even think about crossing the chasm. I replace the outdated, fill-in-the-blanks positioning statement—which I argue is actively harmful because it reinforces the status quo—with a dynamic, 10-step process of deconstruction and reconstruction. The unique contributions of my work are the insistence on starting with your happiest customers to find your true value and the component-based approach that makes positioning a repeatable, logical process rather than a mysterious art form. It’s designed for the modern tech company that can’t afford to be misunderstood in a crowded market.
Reflection
As an AI product engineer, you are often building things the world has never seen before. The biggest risk you face is not technical failure, but market failure due to misunderstanding. My book is designed to mitigate that risk. Its core strength lies in its practicality and actionable nature; it’s a workshop in a book, providing a clear, repeatable process for a concept that is often treated as abstract marketing fluff. The emphasis on starting with ‘best-fit customers’ is a powerful way to ground your strategy in reality, which is crucial when developing novel AI that can be applied in countless ways. However, one must be skeptical about applying this process too rigidly. The path from a ‘cake’ to a ‘muffin’ is rarely a neat, linear 10-step process; it’s messy and iterative. Furthermore, for truly disruptive AI creating a zero-to-one product, you may not have any happy customers to start with. In this scenario, my framework is less of a step-by-step guide and more of a compass for running initial market experiments, helping you define the hypotheses you need to test to find those first happy customers. Ultimately, the book’s greatest significance for the AI field is in forcing a shift from a product-centric view (‘look at my cool algorithm’) to a market-centric one (‘here is the context where my algorithm is obviously awesome’). That shift in perspective is the difference between a celebrated innovation and a brilliant-but-failed experiment.
Flashcards
Card 1
Front: What are the 5 core components of effective positioning?
Back:
- Competitive Alternatives (What customers would use if you didn’t exist) 2. Unique Attributes (Your special capabilities) 3. Value (The benefit your attributes deliver) 4. Target Market Characteristics (Who cares most about that value) 5. Market Category (The context that makes your value obvious).
Card 2
Front: What is [[Positioning Baggage]]?
Back: The disconnect between how product creators see their product (with its full history and original intent) and how a new customer perceives it for the first time. It’s the internal story that often creates external confusion.
Card 3
Front: What are the three strategic styles for positioning in a market?
Back:
- Head to Head: Compete to be the leader in an existing market. 2. Big Fish, Small Pond: Dominate a specific subsegment of an existing market. 3. Create a New Game: Invent and lead an entirely new market category.
Card 4
Front: What is the very first step of the 10-step positioning process?
Back: Step 1: Understand the Customers Who Love Your Product. The entire process is anchored in the perspective of your happiest, best-fit customers.
Card 5
Front: What is the primary flaw of the traditional fill-in-the-blanks positioning statement?
Back: It assumes you already know the best answers for the blanks (your target market, category, and value). It’s a tool for documenting assumptions, not for discovering the best possible positioning.
Card 6
Front: What is the difference between a feature, a benefit, and value?
Back: A feature is what your product has or does (e.g., ‘AI-powered transcription’). A benefit is what that feature enables (‘automated meeting notes’). Value is the outcome that helps the customer achieve a goal (‘save 5 hours a week on administrative work’).
Card 7
Front: What is the goal of the ‘Big Fish, Small Pond’ positioning style?
Back: To carve off and dominate a piece of a larger, existing market where the rules are slightly different, giving your product an edge over the category leader for a specific group of customers with unmet needs.
Generated using Google GenAI