🎙️ Podcast – We’re Not on Easy Mode Anymore EP 01

We Are Not On Easy Mode Anymore, And Maybe That Is A Good Thing

I never planned on starting a podcast. Honestly, I barely planned on having a LinkedIn account. But after a year of ranting with my friend Scott about everything that has gone sideways in sales, it became clear that we had a responsibility. Or at least a calling. Or maybe just enough pent up cynicism to power our own small media empire.

Either way, here we are with a new series called We Are Not On Easy Mode Anymore. The title felt right. It captured that familiar sensation every sales leader feels when they open their dashboard and quietly mutter something that could never appear in a company wide memo.

The world shifted. The playbooks did not. And the gap between those two realities has swallowed entire teams.

This article is the kickoff to the series. It is also my attempt to make sense of the chaos we talked about for an hour straight in our first episode. If you have ever wondered why your messaging is stale, why your SDR team is exhausted, why AI feels both overrated and underused, and why every channel you rely on is collapsing under its own weight, then you and I are about to get very familiar.

It is messy. It is honest. It is uncomfortable. It is exactly what sales needs right now.

If this resonates make sure to check out episode 2.

The Era of Recycling Old Playbooks Has Ended

Somewhere along the way, sales became a ritual. We took the same email templates we wrote twenty years ago and fed them into Outreach like a dehydrated prep meal. Add water. Press send. Call it personalization.

I watched Scott tell the story of how his team at WebEx would fire off mass blasts without even knowing if the addresses were real. They had a spreadsheet filled with every possible variation of a name. It was crude. It was chaotic. It also worked because no one else was doing it.

When a tactic is scarce it looks like strategy. When it is everywhere it becomes noise.

The problem now is not bad messaging. The problem is that the channels themselves are worn thin. Inboxes are flooded. Phones feel radioactive. LinkedIn DMs are a swamp. Buyers stopped paying attention and sellers have not caught up to that reality.

We assume more volume will save us. More emails. More touches. More calls. More sequences. This is like pouring water into a leaking bucket and wondering why the floor is still wet.

If the medium is broken, the message does not stand a chance.

The Personalization Myth That Will Not Die

Inside the recording, we wandered into a familiar debate. The great personalization hypothesis. The idea that if you mention someone's alma mater, or the bus route near their office, or the name of their childhood hamster, they will eagerly book a meeting.

I used to believe in that hypothesis. At Copy AI we ran experiments for months. We generated millions of hyper personal emails. The results were the same every time.

No lift. No meaningful change in reply rates. No extra meetings.

Personalization works only when the context matters and the timing is right. Scott replies to every message about his golf game. Not because it is personal. Because it is relevant to him right now. People do not buy because you say the name of the town they once lived in. They buy because you hit on something they care about today.

We do not need personalization. We need timing.

Which brings me to the real problem.

The Timing Gap That Is Killing Outbound

Right now, outbound is treated like a brute force exercise. Build a list. Blast the list. Repeat. SDRs are measured on surface activity and email tools are evaluated by how much they can automate before someone gets banned from Gmail entirely.

This is how you burn your total addressable market to the ground.

The better question is simple. What would happen if you reached out only at the exact moment when a buyer could actually care?

That has always been the dream. The problem was that no one had a way to do it consistently. And then AI changed that. Not in the hype way. In the practical way.

My team at GTM Engine does one thing extremely well. We look for timing signals. Positive ones. Negative ones. Structural ones. Hiring trends. New leadership. Budget shifts. Department expansions. Announced AI initiatives. Any public breadcrumb that tells us pain is emerging or momentum is building.

Companies do not need you every day. They need you at a few critical moments. If you show up then, the entire channel behaves differently.

If you show up at the wrong time, it does not matter how beautiful your personalization is. You are spam.

SDRs Are Not Broken, But the Role Might Be

This is where the conversation got real. Scott and I have debated the fate of SDRs for years. And honestly, I am no longer convinced the role survives in its current form.

The traditional SDR job was built for easy mode. High volume. Predictable channels. Repeatable templates. A buyer who picked up the phone because no one else was calling.

That world is gone.

Now you are lucky if 1 out of 200 dials becomes a conversation. You are lucky if a prospect even sees your email. And the irony is that many SDR teams are managed as if the channels still behave the way they did in 2015.

The entire motion has become a grinding exercise in futility. You spend a million dollars on a ten person SDR team. They spend half their day clicking buttons between AI powered outreach tools. You get a handful of meetings that are barely qualified.

This is not a team. It is a very expensive hope.

The answer is not to replace the team with an AI bot. Automating an ineffective process does not make it effective. The answer is to evolve the role entirely.

The New Funnel Begins Far Earlier Than the Meeting

Here is the uncomfortable truth. Most buyers would rather watch paint dry than take a meeting with a stranger who interrupts their day.

But they will happily follow someone they believe is interesting. They will engage with someone who teaches them something. They will attend an event that seems useful. They will connect with a person who feels relevant.

This is where I think SDRs need to move. Up the funnel. Into audience building. Into social credibility. Into light touch interactions that do not feel like a shakedown for time.

It is not appointment setting. It is awareness nurturing.

It looks like this.

• Writing three thoughtful posts per week tied to your ICP pain points
• Finding the buyers who shape the conversation and joining them
• Commenting with substance and not with promotional fluff
• Sharing insights that feel earned instead of manufactured
• Building community around your brand instead of chasing meetings
• Running events and micro gatherings where conversations feel organic

You cannot measure the impact of this with the precision of a sequence reply rate. You measure it the way you measure advertising. Over time. In aggregate. Brand equity is not a metric. It is a compounding force.

If you want easy mode, this is not it. But easy mode is dead anyway.

Why In Person Might Become the New Edge

We spent a surprising amount of time on the call talking about dinners, trade shows, and human connection. Which felt almost nostalgic given how much selling has migrated to Zoom.

The funny thing is that the move to Zoom created a new advantage for anyone willing to get on a plane. If your competitors will not shake hands, you should. If they will not walk a show floor, you should. If they will not attend a dinner, you should.

The simplest advantage in any competitive market is doing the thing everyone else refuses to do.

I saw it firsthand this year. Dreamforce. Outbound. HubSpot Inbound. We did not have a booth. We barely had a budget. But we had ambition. And we walked every aisle and talked to every salesperson who could not escape their booth because they were chained there for the day.

That is where the real buying power sits anyway.

The truth is that trust is easier to build over coffee than over a screen. Buyers want that again. They just need someone to give them the excuse.

The Art of Running a Big Meeting Like It Actually Matters

The last twenty minutes of our episode were about something most teams never address until it is too late. Preparing for an important meeting.

Not the night before. Not during the first five minutes of the call. Actually preparing.

Scott explained how his team would choreograph major pitches with the level of detail usually reserved for Broadway performances. Roles. Questions. Transitions. Scenarios. Objections. Every movement rehearsed until it felt effortless.

It reminded me of a comedian I once heard talk about his craft. He said he spent endless hours practicing because he wanted the jokes to feel natural. The work behind the scenes was what created the magic on stage.

In sales we expect the magic without doing the work.

Half the time the AE invites the CEO, the CTO, an SE, an architect, and their manager into the same meeting with zero preparation. Everyone joins with their camera on. No one knows who is running the show. The first ten minutes feel like a family reunion for people who are not actually related.

This is how deals die.

Great meetings are built. They do not happen.

I believe AI should give us a space to do that work. A shared planning room. A preflight checklist. A place where every participant knows exactly why they are there. This is the next frontier for tools like ours. Not replacing sellers. Elevating them.

If Easy Mode Is Gone, What Replaces It

I keep coming back to this question because it sits at the center of every problem we face.

It is not that sales got harder. Sales got exposed.

We relied on channels that were artificially inflated by novelty. Once every company copied those tactics, the advantage disappeared. Now we are left with a marketplace that rewards originality. Creativity. Timing. Precision. Community. Connection.

None of those things can be automated away.

The teams that win now will be the ones that find a new way to stand out. The ones who build trust before they need it. The ones who focus on quality over volume. The ones who adapt faster than the environment around them.

Everything else will slowly fade out.

Maybe that is not a loss. Maybe that is the reset we needed.

The Beginning of a Bigger Conversation

This article is the start of a new season for me. A season of saying things out loud that were easier to avoid. A season of building the kind of company that does not pretend sales is simple. A season of exposing the outdated thinking that keeps teams stuck.

We Are Not On Easy Mode Anymore is not just a podcast title. It is a warning. It is a challenge. It is also a promise that the next era of revenue will reward the people willing to face the discomfort.