SaaS Backwards Podcast

SaaS Backwards Podcast Interviewing CEOs and CMOs of SaaS firms to find out what's working, and lessons learned from what didn’t

Stop feeding the beast.That’s what you’re doing every time you throw more SDRs at a pipeline problem. ▪️ You know the mo...
03/21/2025

Stop feeding the beast.

That’s what you’re doing every time you throw more SDRs at a pipeline problem.

▪️ You know the model’s broken.
▪️ You feel it in the numbers.
▪️ You see it in the burnout.

But it’s hard to kill a sacred cow—especially one called “predictable revenue.”

Here’s the truth:

Cold outbound? Not working.

Third party intent data? Better than nothing, until everyone is chasing the same leads.

Sequences with follow-ups like “Did you read my last email”?

They’re not just ignored—they’re annoying.

Buyers don’t want noise. They want relevance.

And context is the only way to get engagement today.

Yes, it’s hard to scale.

But AI is starting to show real promise—if you use it the right way:

▪️ Not to replace SDRs.
▪️ Not to write more generic emails.
▪️ Not to crank up your spam cannons.

The goal isn’t to create a bigger spam cannon.

It’s more precision.

Point SDRs in the right direction by giving them signals and lead intelligence so they can provide context and relevance to why the buyer should care.

That’s where AI can actually help.

I wrote this to help you sell the change—to your team, your board, and maybe even to yourself.

👇

Not too long ago, when inboxes weren’t flooded with sales pitches, a white paper download actually meant something. SDRs could pick up the phone, call someone who attended a webinar, and have real sales conversations—sometimes even faster than through referrals.

02/26/2025

Imagine this...

You walk into a doctor’s office and say your knee hurts.

The doctor nods, says “Got it” ✅, and writes you a prescription without asking anything else.

Would you trust that diagnosis? No chance. 🚫

Yet, in software sales, reps do this ALL THE TIME in discovery.

They hear a pain point... then rush to a solution without figuring out:

❓ How bad is it? ("How much is this costing you?")
⏳ What’s the cost of doing nothing? ("What happens if this isn’t fixed?")
📆 Is fixing it even a priority? ("When does this need to be solved?")

The result? Deals stall. Buyers disappear. Pipelines dry up.

Peter Cohan explains how to avoid this discovery disaster 🚨—because if you don’t quantify pain, you’ll be in danger of losing the deal to “no decision.”

👀 Watch the clip to learn how to stop this from happening.

02/23/2025

🚨 The biggest mistake in discovery? Thinking pain is enough.

Peter Cohan has analyzed thousands of discovery calls. And most follow the same broken script:
👉 Small talk about the prospect’s background décor
👉 A basic “What’s keeping you up at night?”
👉 A brief discussion of pain
👉 Then… a product pitch

At best, reps spend 10-15 minutes on actual discovery. That’s not enough to uncover value.

The best sellers don’t just surface pain—they quantify it and define the future state.

🛠 Next time you hear pain, ask:
🔹 How long, how much, how often? → Make the pain real.
🔹 What do you need it to be? → Show the path forward.

Pain alone doesn’t sell. Value does.

Watch Peter break it all down in this clip. 👇

02/22/2025

🚨 Your CEO Thinks Marketing is a Gumball Machine—Here’s How to Fix That

For years, marketing success has been boiled down to MQLs, campaign reports, and short-term pipeline.

📊 Jon Miller—who literally helped build the demand gen playbook at Marketo—now says:
👉 We trained CEOs & CFOs to measure marketing like a vending machine.
👉 But today, that model doesn’t work.
👉 We need to move the conversation from lead gen to long-term market impact.

💡 So how do you change the mindset of a CEO/CFO who still thinks in MQLs?

1️⃣ Talk to them like buyers—Ask them, “How did you find your last software vendor?” Spoiler: It wasn’t from a cold email.
2️⃣ Show them why measurement needs a new timeframe—Short-term lead gen is easy to track, but brand & demand creation drive long-term revenue.
3️⃣ Position marketing as a market function, not a service function—Smart CMOs are rebranding themselves as Chief Market Officers.

🚀 The future of marketing isn’t about feeding SDRs leads—it’s about shaping the market.

If your exec team still sees marketing as a cost center, it’s time for a different conversation.

🔗 Watch Jon Miller explain why this shift is critical.

02/20/2025

🚨 Buyers Don’t Want to Talk to Sales—So What’s Your Plan?

77% of millennial buyers want zero interaction with a sales rep until they’ve already made a decision.

80% of their research is done before they ever engage with your brand.

If your entire GTM motion depends on lead forms, SDRs, and outbound, you’re already behind.

📊 Steve Brothers put it best:
👉 Buyers don’t care about your sales process—they care about getting the answers they need.
👉 They’re already in your sales pipeline before they ever talk to you.
👉 If they can’t self-educate, they’re bouncing to someone who lets them.

The Shift We Need to Make:
✅ Stop forcing buyers into your sales process—start meeting them in theirs.
✅ Ditch the outdated “request a demo” model and create self-serve content that actually helps.
✅ Align marketing and sales around enabling buyers—not chasing them.

💡 The companies winning today are selling without “selling.”
Because when a buyer is finally ready, the real question is: Are they ready for YOU?

🔗 Watch Steve Brothers break this down.

02/19/2025

🚨 Your Outbound Sales Playbook is Broken—Here’s the Data That Proves It

Most B2B teams are chasing buyers who aren’t ready—and getting ignored.

📊 Kerry Cunningham’s latest research confirms what we’ve all suspected:

➡️ 85% of B2B buyers initiate the first conversation with a vendor themselves.
➡️ 50% receive outreach for weeks or months before engaging—but ignore it until they’re ready.
➡️ Cold outreach isn’t moving buyers faster—it’s just burning resources.

👉 So what’s the move?

1️⃣ Stop trying to force buyers into a sales cycle before they’re ready.
2️⃣ Invest in demand creation—so when they do engage, they already know and trust your brand.
3️⃣ Build a brand that attracts inbound interest instead of relying on brute-force outbound.

💡 The future of sales isn’t about how many calls you make.
It’s about how many buyers you attract before they even enter the market.

If your pipeline is drying up, this is why.

🔗 Watch the full clip from Kerry Cunningham here:

01/27/2025

"Right place, right time, right ecosystem."

Sometimes success isn’t just about working hard—it's about working hard in the right environment.

This clip from Michael Nee on the SaaS Backwards Podcast nails it:

✅ If you align with the right megatrend, even a stumble can take you farther than relentless effort in the wrong market.

In Silicon Valley, the ecosystem itself can do 90% of the heavy lifting. That same grind in a different context might not yield even a fraction of the results.

The lesson?
Hard work matters.
But where you focus that effort matters even more.

What do you think—is the right environment the ultimate growth hack, or do you believe grit can overcome any odds?

Why Your AI Messaging Is Killing Your Demo PipelineHere’s the brutal truth: “AI-powered” isn’t special anymore. It’s whi...
01/22/2025

Why Your AI Messaging Is Killing Your Demo Pipeline

Here’s the brutal truth: “AI-powered” isn’t special anymore. It’s white noise. If that’s all your messaging says, you’re invisible.

Every day you stick with vague, generic claims, you’re losing potential demos.

Prospects land on your site, skim your headline, and bounce—off your page, and into your competitor’s pipeline.

The problem? You’re talking like it’s 2015. Back then, “AI-powered” turned heads.

Today, it’s table stakes. Buyers don’t care what powers your product—they care about how it solves their specific problem.

This article shows you how to fix that by aligning your messaging with your market’s sophistication. You’ll learn:

- Why buyers ignore generic claims and how to reframe your value.

- The critical step SaaS marketers skip—and how it costs them demos.

- How to use insights that actually matter to stand out in a crowded market.

When you land on a software homepage boasting the phrase "AI-powered," does it inspire you to dig deeper? Probably not. If this were 2015, that claim might have been enough to grab your attention.

01/17/2025

De-Risking Advertising: The Playbook for CROs and CMOs in 2025

Today’s buyers aren’t ignoring your ads because they’re busy—they’re ignoring them because your message doesn’t hit home.

Ken Lempit breaks down a smarter way to de-risk campaigns and drive real results:

👉 Start with insight. Talk to your customers and uncover their real problems—the ones your product solves better than anyone else.

👉 Test before you invest. High-frequency organic posts let you refine your message fast, without draining your budget.

👉 Scale what works. Once you know what resonates, your paid campaigns deliver ROI you can count on.

This isn’t just another trend—it’s how the best CROs and CMOs are winning in 2025.

🎥 Watch the clip to see how it’s done 👉

01/03/2025

Every marketer talks about pain points. But here’s the truth: pain alone doesn’t get deals across the finish line.

Beth McHugh breaks down the critical difference between identifying "pain points" and finding the struggling moment—that point where your buyer's frustration is so intense they have to act.

This isn't just about understanding your audience; it’s about uncovering the deep struggles that create urgency. Because if your buyer doesn’t believe their problem is worth solving NOW, you’ll keep losing to “no decision.”

If you're a SaaS marketer looking to sharpen your messaging, create true differentiation, and turn “maybe later” into “yes, let’s do this,” this clip is for you. Watch now to learn how finding the struggling moment can transform your go-to-market strategy.

🎯 Think attribution is helping your team grow? Think again.Attribution was supposed to bring clarity to sales and market...
12/31/2024

🎯 Think attribution is helping your team grow? Think again.

Attribution was supposed to bring clarity to sales and marketing. Instead, it’s fueling the blame game:
👉 Marketing says, "Look at all these MQLs!"
👉 Sales says, "None of them are closing!"
👉 Meanwhile, your pipeline? Stalled. 🚧

Here’s the truth: buyers don’t follow a straight line.
They’re influenced by dark social 🌒, peer recommendations 💬, and touchpoints attribution tools just can’t measure.

The real problem?
It’s not the tools—it’s the siloed system keeping sales and marketing at odds.

If you’re ready to stop wasting resources and start driving real growth, here’s the fix:
✅ Align around customer outcomes.
✅ Incentivize collaboration over competition.
✅ Stop tracking what’s convenient—and start tracking what matters.

💡 Ready to break free from attribution wars?

Check out our latest post for the full breakdown. 👇

Let’s fix the system, together. 🔧✨

Let’s face it: Attribution is broken. Marketing claims they’re generating plenty of MQLs.

12/27/2024

🚨 Thinking about hiring or becoming a Fractional CRO?

Let’s get real: A true CRO isn’t just a fancy sales title. They’re responsible for aligning all revenue-driving functions—sales, marketing, customer success, and beyond.

Can that be done fractionally?

Nope.

Most fractional CROs are actually just sales leaders. Nothing wrong with that, but let’s call it what it is.

If you’re a company considering this move, or thinking about stepping into the role yourself, watch this before you decide. It’s time to set the record straight.

👉 Watch now and let me know if you agree!

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