Growth & Strategy
Personas
SaaS & Startup
Time to ROI
Medium-term (3-6 months)
Last year, I watched a brilliant SaaS founder explain their product for 20 minutes to a potential customer. Perfect demo, flawless feature walkthrough, impressive tech stack. The prospect's response? "Looks interesting, but we're already using [competitor]." Sound familiar?
Here's the uncomfortable truth I learned working with dozens of B2B SaaS clients: your product positioning isn't a product problem—it's a trust problem. Most founders are so focused on building features that they forget to build the narrative that makes people care.
After helping clients pivot from feature-first to positioning-first strategies, I discovered something counterintuitive. The companies that won market share weren't necessarily building better products. They were building better relationships with their market's existing beliefs.
In this playbook, you'll discover: How to identify why prospects choose competitors over you, my framework for positioning SaaS as services rather than products, the specific messaging shifts that transformed trial-to-paid conversion rates, and why founder-led content beats product demos every time. Plus, I'll share the exact positioning experiments that helped one client go from "just another tool" to "the obvious choice" in their niche.
Ready to stop competing on features and start winning on positioning? Let's dive into what actually works.
Market Reality
What the positioning gurus won't tell you
Walk into any SaaS conference and you'll hear the same positioning advice repeated like gospel. "Find your unique value proposition." "Differentiate on features." "Create comparison charts showing why you're better." The positioning industrial complex has convinced everyone that winning means being objectively superior.
Here's what they typically recommend:
Conduct competitive analysis and find feature gaps
Build a positioning matrix comparing capabilities
Create messaging around being "better, faster, cheaper"
Launch with clear differentiation statements
Focus on rational decision-making criteria
This advice exists because it feels logical. Business buyers should make rational decisions based on objective criteria, right? And there's some truth here—clear positioning matters, competitive differentiation is important, and you need to articulate value.
But here's where conventional wisdom falls short: It assumes people make buying decisions based on spreadsheets and feature comparisons. In reality, most B2B software purchases are emotional decisions justified with rational arguments afterward. People don't switch tools because yours is 10% faster—they switch because they trust you to solve their problem better than their current solution.
The traditional approach treats positioning like a product specification sheet. But winning positioning isn't about being objectively better—it's about being subjectively obvious for your specific audience.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
When I started working with B2B SaaS clients, they all came to me with the same fundamental issue disguised as different problems. "Our conversion rates are too low." "Prospects ghost us after demos." "We lose to competitors on price." But after analyzing their funnels and sitting in on sales calls, the real issue became clear.
They had a positioning problem, not a product problem.
Take one client I worked with—a project management SaaS for creative agencies. Their product was genuinely innovative, with features their competitors didn't have. But here's what I observed: when prospects came through paid ads or cold outreach, they'd sign up for trials but rarely convert to paid plans. The founders were convinced they needed better onboarding or more features.
So I dug deeper into their analytics and user behavior. Here's what I found: prospects were treating their SaaS like a commodity product. They'd compare it against established players like Monday.com or Asana, looking for the obvious "better" choice. But in a crowded market, being objectively better isn't enough—you need to be obviously different.
The breakthrough came when I analyzed their highest-converting traffic source: referrals from the founder's personal LinkedIn content. These weren't prospects comparing feature sets—they were people who already trusted the founder's expertise in creative project management. They didn't sign up to try another tool; they signed up because they believed this person understood their specific challenges.
That's when I realized we were treating SaaS positioning like e-commerce product positioning. We were optimizing for transactions when we should have been optimizing for relationships. SaaS isn't really "software as a service"—it's expertise as a service, delivered through software.
Here's my playbook
What I ended up doing and the results.
Based on this insight, I developed what I call the "expertise-first positioning" approach. Instead of positioning the SaaS as a better tool, we positioned it as access to specialized knowledge that happened to be delivered through software.
Here's the step-by-step framework I implemented:
Step 1: Identify the Real Job-to-be-Done
Most SaaS founders think their job is to provide software functionality. But that's not what customers actually hire your SaaS to do. They hire it to achieve an outcome they can't achieve with their current situation.
For my project management client, prospects weren't hiring them to "manage projects better." They were hiring them to "avoid the agency chaos that kills profitability and burns out creative teams." This distinction completely changed how we talked about the product.
Step 2: Position Founder Expertise, Not Features
Instead of leading with software capabilities, we led with the founder's specific experience solving this exact problem. The messaging shifted from "Our tool has better Gantt charts" to "After running creative agencies for 10 years, here's how I solved the project chaos problem—and built software to systematize the solution."
Step 3: Content-Led Positioning Strategy
This is where most positioning efforts fail—they stop at messaging instead of building a distribution engine. We implemented what I call "demonstration before declaration." Instead of claiming expertise, we demonstrated it through content that solved real problems.
The founder started publishing weekly LinkedIn posts sharing specific project management insights from agency work. Not generic productivity tips—tactical solutions for creative project challenges. Each post ended with a soft mention of how these insights were built into their software.
Step 4: Message-Market Fit Through Iteration
We treated positioning like a hypothesis to be tested, not a statement to be defended. Every piece of content, every sales conversation, every customer interview became data about whether our positioning was resonating.
Within three months, we had clear evidence: prospects who discovered the SaaS through founder-led content converted at 3x the rate of prospects from traditional marketing channels. They weren't evaluating features—they were buying into an approach to solving their problem.
Trust Building
Position expertise first, software second—people buy solutions from people they trust
Channel Strategy
Use founder-led content to demonstrate rather than declare your positioning
Message Testing
Treat positioning as a hypothesis to iterate, not a statement to defend
Distribution Focus
Build positioning into your content strategy, not just your pitch deck
The results spoke for themselves, but not in the way most SaaS metrics typically show success. Instead of just improving conversion rates, we fundamentally changed the conversation prospects were having with the business.
Quantitative improvements: Trial-to-paid conversion increased from 8% to 24% for prospects who discovered the SaaS through founder-led content. Average sales cycle shortened from 6 weeks to 3 weeks. Customer acquisition cost decreased by 40% as organic content replaced paid acquisition for qualified leads.
But the qualitative shift was even more significant. Sales conversations stopped being "convince me why you're better than Monday.com" and became "help me implement your approach." Prospects weren't shopping for tools—they were enrolling in a methodology.
The positioning shift also solved an unexpected problem: customer success and retention. Because prospects understood exactly what they were buying into, they used the software more intentionally and achieved results faster. This created better case studies, which reinforced the positioning in a virtuous cycle.
Most importantly, this approach was sustainable. Instead of constantly battling competitors on features, they owned their unique perspective on the problem. New entrants couldn't simply copy features to compete—they'd need to build equivalent expertise and trust.
What I've learned and the mistakes I've made.
Sharing so you don't make them.
Here are the seven critical lessons that emerged from repositioning SaaS products as expertise delivery systems:
Positioning is distribution, not just messaging. Your positioning strategy needs to be inseparable from how you reach your market.
Founder expertise is your most defensible moat. Features can be copied, but specific experience and perspective cannot.
Demonstrate before you declare. Content that solves problems is infinitely more persuasive than content that claims to solve problems.
Positioning is iterative, not fixed. What resonates with your market will evolve as you learn more about their real motivations.
Trust beats features in B2B decisions. People choose software from people they believe can solve their specific problem.
Narrow positioning enables broader reach. The more specific your expertise, the more clearly qualified prospects can identify you as their solution.
Sustainable positioning requires owned distribution. You can't build lasting market position on rented channels alone.
The biggest mistake I see founders make is treating positioning as a marketing exercise instead of a business strategy. Your positioning should inform your product roadmap, content strategy, and go-to-market approach—not just your homepage copy.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS startups, implement these positioning fundamentals:
Position your founder's expertise, not just your product features
Create content that demonstrates your approach to solving the problem
Test positioning through content engagement before scaling sales efforts
Focus on job-to-be-done rather than feature comparisons
For your Ecommerce store
For ecommerce stores, adapt these positioning principles:
Position founder expertise in your product category or customer needs
Use content to demonstrate product knowledge and customer understanding
Focus on customer outcomes rather than product specifications
Build trust through educational content before pushing sales