The Real Reason You’re Losing Deals (And How to Fix It) – Deep Dive for SDRs & AEs:
This isn’t another fluffy LinkedIn list of “Top 5 Sales Tips.” In this raw and in-depth episode, Eric Finch and Connor Murray (Datadog Enterprise AE) break down real lost deals—step-by-step. If you’re an SDR looking to promote or an AE trying to crack mid-market and enterprise, this episode will save you months of trial and error.

We unpack brutal losses that looked like wins until the final hour, including:

• Getting outmaneuvered by cloud partners like GCP and AWS

• Losing 6-month sales cycles via email because of missed executive priorities

• How selection firms quietly stack RFIs against you

• Why being “single-threaded” will kill your pipeline—and what to do instead

• How to push back when demos don’t align with true business goals

• The difference between working with power vs. taking their word as gospel

• Tactical ways to use onsite meetings and internal champions to accelerate cycles

And yes—we also cover how we turned those battle scars into wins, including how to reframe deals, co-sell smarter, and push back without losing credibility.

Whether you're just getting your first AE role or trying to break into enterprise, this episode is packed with hard-earned, unfiltered sales lessons you won’t find anywhere else.

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