Jason Oakley
How easy is it to buy your product? If you asked a customer, what do you think they’d say?
Chances are, it’s worse than you think. And that’s a problem, because when buyers are faced with uncertainty, doubt, and confusion, they often fallback to the easiest choice. Doing NOTHING. In fact, Studies show that 40-60% of deals end without a decision.
Why? Mainly because buyers are afraid of making the wrong choice. And if you believe this famous Gartner graphic below, buying a B2B product can be a scary, overwhelming process.
If you want more buyers to say “yes,” you need to make the process simple and clear. Each step needs to make them feel more confident in your product, not less. And that’s where buyer enablement comes in.
Buyer Enablement is all about making your buyer feel more confident in purchasing and using your product. In practice, it looks like:
- Stripping out unnecessary steps in the buying process
- Making it super easy to find information about your product and pricing
- Clearly laying out your implementation process so everyone knows what’s next
- Not hiding or gating important info behind a sales rep
- Sharing clear, consistent product messaging
- Providing real customer stories and proof points that build trust
When you get these pieces right, you can build a journey so effortless that buyers choose you for that reason alone.
Where most companies get it wrong
Having a clear buyer journey map is one of the most valuable tools in product marketing. The trouble is that no one agrees on how real buyers actually move from awareness to decision to advocacy.
Most companies end up creating their own “sales process” and then try to force that onto buyers.
Even the content and collateral you create for customers often isn’t focused on them. For example, have you ever made a one-pager based solely on the specs from a sales rep? Or written a product page just for SEO?
Chances are, those resonated about as well as a webinar on a Friday at 4 p.m.
How to map your buyer journey
The process for mapping your buyer journey and improving buyer enablement can be broken down into five steps:
- Gather: Collect all the data, insights, and feedback you can about your buyers.
- Map: Visualize what the journey actually looks like for your target buyers, including their triggers, actions, feelings, and objections.
- Analyze: Measure the conversion rates between each stage and identify the biggest drop-offs, friction points, and areas where buyers feel most unsure
- Recommend: Identify opportunities to improve your buyer enablement and fill the gaps you’ve uncovered.
- Implement: Put your solutions into action, measure what’s working, and keep the cycle going.
Treat your buyer journey as a living system, not a static document. Every new deal or piece of customer feedback is a chance to make it better, so schedule a quarterly review to keep it fresh and useful.
How to use the framework step-by-step
Step 1: Gather real buyer insights
Before you start mapping your buyer journey, you need real customer insights. It’s impossible to map accurately if you’re relying on internal assumptions alone.
Take Target, for example. When they expanded to Canada, they quickly opened over 100 stores. They assumed Canadian shoppers were “just like” U.S. ones and would accept similar pricing, product mix, and experience.
The result? Stores suffered from empty shelves, higher perceived pricing, and disappointing product selection. Target pulled out within two years, losing more than $2 billion.
Examples like these really highlight why talking to, and understanding your customers is so important.
So what does that look like in practice?
- Interview real buyers you either won or lost (aka win-loss interviews)
- Create a centralized knowledge base of interview transcripts, CRM notes, sales call recordings, emails, and chat conversations that you can analyze in your LLM.
- Look for “moments of truth” — key points where buyers progressed or got stuck
Step 2: Map the journey
Now comes the fun part. Turning those insights into a visual map that captures what buyers actually do and think when evaluating, choosing, and using your product.
The PMM Jetpack includes a template to help you get started quickly, but I’ll walk you through each step below.
TEMPLATE: BUYER JOURNEY MAP
Use this template to help you map your buyer journey and spot opportunities for better buyer enablement that will help improve your conversion rates.
Buying Stages
A common buyer journey framework goes like this: Awareness > Consideration > Purchase > Onboarding > Advocacy.
Here’s what those stages generally mean:
- Awareness: When a potential buyer first realizes they have a problem or need and starts searching for info or solutions.
- Consideration: The buyer is actively exploring different options, and comparing products or vendors that could solve their problem.
- Purchase: The decision point. The buyer chooses a solution, gets internal buy-in if needed, and completes the purchase.
- Onboarding: After buying, the customer starts using the product, setting it up, and learning how to get value from it.
- Advocacy: The customer is happy with their experience and begins promoting or recommending the product to others (e.g., through reviews, referrals, or case studies).
Tip: Feel free to adjust these stages as you learn more about your ideal customers buyer journey.
Sales/CS Stages
Now, this may sound hypocritical, but the next step is to map your internal process to the buyers’ process. This is an important step because it gives you context around what your company is doing (and what your goals are) at each stage of the buyers’ journey.
Also, since this likely how you structure your reporting in your CRM, it’s going to allow you to track conversion rates and spot problem areas in your funnel.
As you map the stages of your funnel, gather two vital metrics:
- Conversion Rate: The percentage of buyers that move from one stage to the next.
- Duration: The number of days it takes to move a buyer from one stage to the next.
Those two metrics ☝️ are going to help you spot problems in your buyer journey.
Tip: In the Buyer Journey Mapping Template you’ll see a generic process to start, but you’ll want to tailor these stage names to map directly to your internal process. Schedule an hour with a member of your revenue operations team so they can help you map it out accurately and gather the right metrics.
Buyer Touchpoints
These are all the interactions you have with the buyer along their journey: meetings, emails, visits to your website, resource downloads, etc.
For example, at the consideration stage, touchpoints might include a discovery call, a product demo, or follow-up emails. They might also be browsing your website or reading case studies.
Watch out for touchpoints that may be causing friction; either too many unnecessary steps, or missing ones that could help the buyer move forward.
Buyer’s Objective
This is about stepping into your buyer’s shoes. What are they trying to accomplish at this stage of the process? Could be something as simple as trying to schedule a demonstration, or trying to present an internal business case for budget approval.
Remember not to confuse this with your own internal motivations. Those don’t matter here. You’re trying put yourself in the shoes of your buyer, so keep their perspective front and center.
Struggles and Objections
This part is gold for finding ways to improve your buyer enablement. Identify all of the things that confuse, frustrate, or scare your buyers. These could be questions they ask or objections they raise on calls, but also things that often go unsaid and only come out later in win-loss conversations. Things that ultimately lead to fear and doubt that keeps them from buying.
This is not a section you’ll be able to complete on your own. Up-front customer research is critical here, but you can also get a lot from interviewing your sales and CS reps. Even consider scheduling time to complete this part of the map with them.
Stakeholders
Research shows that most buying decisions involve 6-10 stakeholders. So assuming that every stage only involves your one champion is a mistake. Identify all of the other stakeholders that come into the picture as they move through the buyer journey.
For each stakeholder ask yourself: “Is this person someone we interact with directly, or will my champion need to convince separately.”
Current Assets
This is where you list all of the resources, content, and tools you offer buyers at each stage of their journey. Examples could include things like ROI calculators, pitch decks, interactive demos, implementation guides, pages on your website.
When you’re writing website copy, remember that it’s a massive buyer enablement asset. Probably your most valuable. It’s where the majority of your buyers go first to learn about your product. So make it clear, useful, and easy to navigate.
Step 3: Analyze conversion rates and spot the gaps
Time to put on your investigator hat 🕵️ and identify where things are breaking in your funnel. Start by taking time on your own to review each stage and the information you’ve gathered, and prioritize stages where you feel there are the biggest problems.
The best places to look are:
- Stages with low-performing conversion rates
- Stages that take way longer than they should
- Struggles and objections that you aren’t addressing
Once you’ve made your initial assessment, bring in other team members like leadership, sales, customer success, and marketing. Doing a quick workshop can lead to great insights and help align everyone. Your goal here should be to prioritize your top problem areas that, if improved, will drive the most meaningful impact for your business.
Prioritization is everything here. It’s tempting to want to fix everything, but your real value comes from identifying and tackling the most critical issues.
Step 4: Recommend improvements
Now we’re at the fun part: brainstorming and prioritizing how to fix those biggest pain points in your buyer journey. The goal here is to find the initiatives that can have a big impact without requiring a ton of effort.
It’s best to do this as a team, in a workshop or small brainstorming session, so you can get diverse perspectives and come up with the best ideas.
Step 5: Implement
This where the rubber meets the road. You’ve mapped your buyer journey, pinpointed the problem areas, and prioritized how to fix them. Now it’s time to take action.
Since every business is different, I can't tell you what your potential opportunities will be, or the changes you'll implement, but here are a number of example scenarios to hopefully get your wheels turning.
Example 1: Stuck in IT Review
After interviewing 10 prospects, the PMM discovered that most buyers got stuck in “IT review” because the product security documentation wasn’t public.
- ✅ Fix: They published a transparent security FAQ and SOC 2 summary.
- 📈 Result: Sales cycle time dropped 18%, and fewer deals stalled in procurement.
Example 2: Hidden Pricing
The team learned that buyers consistently asked for pricing before scheduling demos, but the website hid it.
- ✅ Fix: They added a “starting at” tier on the homepage and built a demo that highlighted ROI.
- 📈 Result: Demo conversion rate increased by 25%.
Example 3: Smoother Trial Conversion
After mapping the buyer journey, the PMM saw most trials stalled because users didn’t know what success looked like in the first week.
- ✅ Fix: They added a “Day 1–7 checklist” and in-app milestone prompts.
- 📈 Result: Trial-to-paid conversion went up by 22%.
Example 4: Reducing Demo Drop-Offs
The team found that half of buyers left demo requests incomplete after hitting a long form.
- ✅ Fix: They cut the form from 8 fields to 3 and added an instant self-guided demo option.
- 📈 Result: Demo completions rose 40%, and lead-to-meeting rate doubled.
Example 5: Surfacing Product Differentiators Earlier
Mapping showed buyers only learned the company’s biggest differentiator halfway through sales calls.
- ✅ Fix: The PMM updated website copy and intro decks to feature the differentiator upfront.
- 📈 Result: Win rate improved by 12% against main competitor.
Example 6: Removing Hidden Friction in Procurement
Buyers said their legal teams delayed sign-off due to missing compliance docs.
- ✅ Fix: The PMM published a “Security & Compliance Center” with downloadable PDFs.
- 📈 Result: Average contract cycle shortened by 10 days.
Example 7: Fixing the Content Gap Between Awareness and Evaluation
Analysis revealed a big drop between top-of-funnel blog traffic and demo requests.
- ✅ Fix: They created mid-funnel comparison guides and ROI calculators tied to blog CTAs.
- 📈 Result: MQL-to-SQL conversion rate increased from 14% to 26%.
Example 8: Aligning Sales Follow-Up Timing
Journey data showed reps followed up too late — buyers had already gone cold after the demo.
- ✅ Fix: PMM worked with RevOps to automate same-day follow-ups with tailored content.
- 📈 Result: Second-meeting booking rate jumped 35%.
Example 9: Highlighting Integration Proof Early
Buyers kept hesitating because they weren’t sure integrations would work with their stack.
- ✅ Fix: Added an “Integrations” section with GIFs and one-click setup videos on the homepage.
- 📈 Result: Demo requests mentioning “integration” concerns dropped 60%.
Example 10: Improving Post-Trial Nurture
Many users went inactive right after their free trial ended.
- ✅ Fix: The PMM built a three-email sequence showcasing success stories and time-sensitive upgrade offers.
- 📈 Result: Reactivation rate improved by 50%, and churn during trial-to-paid fell sharply.
Buyer Enablement is not a one-time thing
It’s the ongoing effort of removing doubt and making your buyers feel confident.
The article gave you a simple, repeatable system: Gather → Map → Analyze → Recommend → Implement. When you run this cycle regularly, you’ll uncover friction points, and make changes that boost conversions and shorten sales cycles.
Try this over the next month: talk to five recent buyers and capture what triggered their actions, what confused them or gave them doubt, and what ultimately drove their decision. Then create your map, circle the top two bottlenecks, and prioritize one improvement.
You don’t need to think of it as a major project. Just small incremental changes over time. Start small, measure what happens, and iterate. Your buyers will feel the difference, and so will your pipeline.