#48 - Real Sales Cycles That Made (And Broke) Us in Tech Sales

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 AWSLosing 6-month sales cycles via email because of missed executive prioritiesHow selection firms quietly stack RFIs against youWhy being “single-threaded” will kill your pipeline—and what to do insteadHow to push back when demos don’t align with true business goalsThe difference between working with power vs. taking their word as gospelTactical ways to use onsite meetings and internal champions to accelerate cyclesAnd 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.Want live coaching from reps who’ve actually done it?Join the community or get training at HigherLevels.com