This one thing is killing your deals

“Hey, that’s me!”

When you’re reaching out to prospects, can they see themselves in your messaging?

When you’re asking discovery questions, can they feel their pain?

When you’re demoing, can they see their context, their world, and how they become better?

For the vast majority of founders I meet - the sales process is selfish, at first.

It comes across to prospects as:

“Hey, look at me. I’m great. I have this fancy new startup. It’s really cool. Exactly what I wish I had when I was doing my job. I’m awesome. Book a meeting with me.”

And this framing continues in their intro call. In their demo. In the follow ups.

Here’s the thing.

Sales isn’t about you. It’s not about pushing product. It’s not about convincing. Or persuading.

It’s about understanding. Understanding the pain the prospect has. The problems these pains are causing to other parts of the business. And how they can get to a better state of doing things.

Your solution is the LAST thing they care about.

When you understand this, you can build a sales process that’s actually helpful, and leads to more deals being closed:won.

Let’s unpack this more.

Table of Contents

• Why you don’t matter, yet

• Stop being selfish

• How to bring pain into your sales cycles

Why you don’t matter, yet

As much as it would be nice to just create a cool product, and have a line-up of customers just begging to buy it, that never happens in B2B SaaS sales.

In the early days, nobody knows about you. You don’t have a ton of customers yet. You don’t have a track record of success. So you’re automatically a risky option.

And risk is one of the worst things to introduce to a process.

That’s assuming that prospects know about you. Which they don’t. So dropping your name, startup, anything related to what you’re doing is rarely relevant.

And here’s why.

Prospects are constantly thinking about different problems that exist in their world. This thing isn’t working. My boss is on me to deliver. I’m worried about losing my job.

Your startup is not entering their top 10 thoughts. Likely not their top 50 thoughts.

And that’s just one person’s worry. In most B2B SaaS sales cycles, decisions are made by committee. 3-5 people usually. Sometimes more if you’re selling to enterprise. So then you multiply these problems and thoughts across all of these folks.

And guaranteed nobody is thinking about you.

But what are they thinking about? They’re thinking about how painful it is to get something done, in their role. And they’re thinking about how this is stopping them from achieving their goal. And they’re thinking about what happens if they can’t achieve their goal. And they’re weighing all of the different problems that exist to prioritize which one do they tackle first.

So your sales process - everything from your ICP definition, to your outreach, to your discovery, and demo - needs to reflect this state of pain.

Stop being selfish

Let’s circle back to how I started this newsletter.

“Hey, that’s me.”

Your prospect needs to see themselves - their world, their context, their workflows - in everything you do from a sales perspective.

When they see this, you automatically become the best solution to their problem.

Often founders are told to focus on the solution.

But they forget the real definition of a solution.

It says it right here - problem or dealing with a difficult situation.

Features, functionality, and product without the context of pain rarely gets you anywhere.

So your positioning, outreach, discovery, and demos should be centered around your prospect’s pain.

How to bring pain into your sales cycles

Here’s how to focus on pain in different parts of the sales cycle:

• ICP definition + targeting: When you’re coming up with your ideal client profile, don’t focus on “filters” like funded or 200-500 employees. It tells you nothing about the pain the prospect is experiencing. Focus on identifying traits that signal the pain might exist. Let’s pretend you're helping founders who are struggling with managing delivery from their eng team. Stuff that might identify issues could be a fractional CTO who has a distributed eng team spread across many time zones. Then your targeting would look at eng team located somewhere else than HQ location of the company. ICP/targeting should help you isolate pain, not just a type of company..

• Relevance + messaging: When doing outreach, if you’ve narrowed down a few qualifying filters in your targeting, the message tends to write itself. You show your research, and write a pain-based message. This will make your outreach much more relevant. Example: Hey Joe, saw you just brought on a fractional CTO to manage your overseas dev team. A lot of non-technical founders are struggling with getting consistent commits and delivery from devs spread across timezones. Leads to features getting delayed. Does this match what you’re seeing?

• Discovery: A lot of founders do qualification over discovery. Qualification is selfish - usually covers what tech do you use, people they have, workflows, etc., to see if your product would be a fit. What it misses are painful moments in the workflow, how that’s impacting other parts of the business, and what happens if they don’t solve for it soon. Discovery needs to uncover a $1M problem to create enough momentum for a company to fix the issue. You need to probe on how the pain manifests in the business.

• Sales story: Your story should summarize a lot of the pains you’ve uncovered in your discovery. When you’re going through your pitch, there should be moments where they recognize themselves in the story. It should prompt them to share examples and stories of their own. When your story is about them, you get reactions.

• Demo: Your demo should be structured in chapters, centered around painful workflows. It should summarize the context in which the workflows are important, the problems with existing workflows, the capabilities they’ll gain. Then show exactly how the workflow will solve their problem. Then ask a pain-related question that makes them think about how the workflow compares to what they’re doing now.

• Follow-ups: Your follow-up emails after each call should articulate the pain, how it impacts the business, how your product helps solve the painful workflows, and any action items or next steps that were discussed to move the deal forward.

Do this, and you’ll immediately see a positive impact on how your deals are going.

There are 4 motivators for buying decisions, and they go in this order of importance:

1. Current pain

2. Current gain

3. Future pain

4. Future gain

When you talk about yourself, and the outcomes you can drive, you come across as a “future gain.” Which is the least likely reason a B2B SaaS will buy a product.

So focus on current pain, and things will run much smoother.

Let me know what you think of the newsletter! Always want to cover topics that you care about.

For more practical early-stage sales tips, connect with me on LinkedIn.

If you’re looking for more hands-on help implementing your first sales process, reach out for coaching packages.