What if a single, well-timed email could change the trajectory of your entire career? In this episode of Who Got Me Here, Annie Riley sits down with Drew Sechrist, one of Salesforce’s earliest employees and the founder & CEO of Connect the Dots. Drew shares how a cold email to Marc Benioff landed him a front-row seat on Salesforce’s rise from pre-revenue to over $1B—and how intentional relationship-building made him a top-performing sales leader. Together, they unpack why meaningful networking isn’t about volume, how to stand out when everyone around you is an A-player, and why imposter syndrome is often a signal, not a weakness. This conversation is a masterclass in being curious, being intentional, and building relationships that compound over decades.
00:00 Introduction to Drew Sechrist
00:48 Drew's Early Career and Salesforce Journey
01:45 The Power of a Well-Timed Cold Email
05:48 Navigating Relationships and Networking at Salesforce
08:50 Mentorship and Early Sales Lessons
16:14 Building Community Across Geographies
18:55 Learning from Mistakes and Iterating
20:18 The Importance of Feedback in Networking
23:16 Tools for Building and Maintaining Relationships
27:51 Final Thoughts on Relationship Building
Cold outreach works when it’s targeted and informed. Drew’s email to Marc Benioff wasn’t clever—it was relevant. He understood the problem, the timing, and why the idea mattered.
Practical takeaway: Before reaching out, ask:
If you can’t answer those, don’t hit send.
As automation increases and responses drop, trust becomes scarcer—and more valuable.
Practical takeaway: Stop relying solely on cold outreach.
The future doesn’t belong to the loudest inbox—it belongs to the most trusted network.
One of Drew’s biggest accelerators was finding mentors—sometimes in unexpected places—and being honest about what he didn’t know.
Practical takeaway: Identify one person this month and say:
“I’m trying to get better at X, and I think you’re great at it. Could I learn from you?”
Most people want to help. Waiting to “deserve” mentorship just slows you down.
@ 2024 Who Got Me Here, Inc.
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