I caught up with two sales leaders recently — both seasoned, both with strong track records, both ethical operators. And both had just washed out of their latest sales roles in under 6 months.
That seemed… odd.
So I dug deeper. What I found was a common thread that might surprise you: Neither had really spent time with their teams in person. Almost none at all.
Case #1: The Top 10% AE Who Now Couldn’t Close
This rep had crushed it at multiple well-known startups. Always in the top 10%, at least for a while. Strong closer, respected by his peers.
He joined an SF-based startup remotely from the East Coast. He never met anyone face-to-face during the interview process. He never flew out to the west coast office before — or after — signing the offer letter. In fact, he never visited the office once. All he did IRL was attend a team event in person several months after starting.
Here’s the kicker: A few months in, as he was struggling to hit quota, the team organized a meetup about 2 hours from his home. He didn’t show. He said it was too long a drive.
The Result? He struggled to learn the product, couldn’t build internal relationships, and closed almost nothing. His boss stopped routing him leads after he didn’t come to the meetup. Managed out in 5 months.
Case #2: The CRO Who Lost Half His Business
This one stings more because the stakes were higher.
An experienced CRO was recruited to lead a 50-person global sales organization. Two main segments: Enterprise (mostly US-based) and SMB (primarily Latin America). SMB was driving about 40% of revenue.
He spent maybe 3-4 days total in person with the CEO during his entire tenure, the rest on Zoom. All their strategic planning happened over Zoom. He never really understood the CEO’s vision for the SMB business or why it mattered so much to the company’s growth trajectory.
He met regularly with the enterprise team — joined their QBRs, joined some customer meetings, built some relationships. But the SMB team in Latin America? Never visited once. Not even a quick trip to Mexico City or São Paulo to understand how they operated.
The SMB team had different challenges: smaller deal sizes, higher velocity, different competitive landscape, unique cultural dynamics around relationship-building. Without understanding any of this firsthand, he couldn’t provide the leadership they needed.
Result? The SMB team saw 60%+ attrition within 4 months. Top performers left for competitors. Pipeline dried up. The segment that was supposed to be their growth engine became a liability.
SMB revenue dropped 35% quarter-over-quarter. CRO was out in 6-7 months.
The Fragility Factor
Remote work isn’t going anywhere. But there’s something about never breaking bread with your team — never looking them in the eye, never understanding their daily reality — that creates fragility. I see this way too often today.
You miss:
- Cultural nuances that affect performance
- Product knowledge that only comes from organic conversations
- Trust that builds when you show up where your people are
- Early warning signals that save your bacon
- Strategic alignment with leadership that only happens face-to-face
The Bottom Line
Maybe there were other issues here. There always are.
But I was shocked that two proven performers never invested in the basic human connection with their teams and key stakeholders. In sales — where relationships drive everything — that’s not just a missed opportunity.
It’s a career killer.
A great related post here:
