Webinar Details
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.
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.
Session Highlights
“Easy Mode” in sales is over.
The environment has changed while most teams still use outdated playbooks. Channels are saturated, attention is fragmented, and past tactics no longer work. Sales isn’t harder; it’s simply been exposed.
Old playbooks fail because the channels themselves are broken.
Cold email, cold calling, and LinkedIn are overcrowded. More volume cannot fix channels that no longer hold attention. If the medium is failing, the message can’t break through.
Personalization is overrated; timing is what actually matters.
Hyper-personal facts do not increase replies. What moves people is relevance in the moment. Outreach only works when it aligns with what the buyer cares about right now.
The timing gap is killing outbound.
Outbound still runs on brute force instead of intelligence. The future is signal-driven outreach triggered by real buyer changes like hiring shifts, leadership moves, budget changes, and new initiatives.
The SDR role was designed for a world that no longer exists.
The traditional high-volume, template-driven SDR motion collapses in today’s environment. The role must evolve rather than be automated away.
The new funnel begins long before the meeting.
Buyers engage with people who teach, share, create, and participate. Modern SDRs should focus on building audience, credibility, and community instead of chasing appointments.
In-person interaction is becoming a new advantage.
As everyone defaults to virtual selling, showing up physically becomes a differentiator. Trust forms more easily over coffee than over Zoom.
Big meetings fail because teams do not prepare.
High-stakes meetings need rehearsal, clarity, roles, and structure. Most teams show up disorganized, and deals die from lack of preparation. AI should help create coordinated pre-meeting alignment.
What replaces easy mode?
The next era rewards originality, creativity, timing, precision, community, and human connection. Not automation. Not volume. Teams that adapt will win.
This is just the beginning.
The piece opens a larger conversation about rebuilding how sales works and discarding outdated thinking. The challenge is to embrace discomfort and evolve.
