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What We Lose When We Go Fully Remote
There’s no shortage of content celebrating the benefits of remote work—flexibility, productivity, fewer commutes, more time with family, and an endless stream of digital tools that keep us “connected.” All of that is real. And yet, I find myself thinking more about the other side of the equation: what’s lost. Because for all the efficiency we’ve gained, something fundamental has quietly slipped away. The Missing Moments Between the Work When everything happens in a virtual m
redmondgregory
Nov 21, 20252 min read
The Lost Art of Discovery
There’s an interesting (and troubling) trend I’ve noticed in sales conversations lately. Too many salespeople jump on an introductory call with one goal in mind: schedule a demo. But here’s the problem — what good is a demo if your solution doesn’t actually solve a problem for the prospect or deliver measurable ROI?If there’s no clear pain point or value alignment, the demo becomes a waste of time for everyone involved — the salesperson, the solutions engineer, and most impor
redmondgregory
Nov 7, 20252 min read
Running a Start-Up Is Not for the Faint of Heart
There’s nothing quite like building something from scratch. And there’s nothing quite as humbling, either. Founders quickly learn that...
redmondgregory
Oct 12, 20252 min read
When CIOs and CISOs Don’t See the Value in Your Solution
If the people using your solution aren’t the ones controlling the budget—and they aren’t communicating value up the chain—you’ve got a...
redmondgregory
Sep 12, 20251 min read
Cost of Making a bad VP of Sales Hire
A bad hire for a VP of Sales can cost hundreds of thousands to even a million dollars or more, encompassing direct recruitment costs,...
redmondgregory
Sep 10, 20251 min read
For CEOs Who Can’t Afford Another Year of Stalled Growth
Every CEO I talk to says the same thing: “We can’t go through another year like this.” Stalled growth isn’t just frustrating—it’s...
redmondgregory
Sep 10, 20251 min read
The Hidden Reason CEOs Stay Stuck in Flat Revenue
When revenue stalls, most CEOs look at the obvious culprits: Not enough leads Wrong pricing Product gaps Sales team underperforming But...
redmondgregory
Sep 10, 20251 min read
From Chaos to Clarity: Bringing Discipline to Sales with Fractional Leadership
One of the biggest challenges I see in growth-stage companies is sales chaos . Reps chasing every opportunity with no prioritization...
redmondgregory
Sep 10, 20251 min read
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