Why Your Best Deals Keep Slipping Away: Insights from Win-Loss Analysis Expert

Despite stacks of promising pipeline, too many SaaS deals ended in heartbreak rather than high-fives in 2023.

So what's causing so many late-stage opportunities to mysteriously crumble?

I sat down with Mike Hoffman, founder of win/loss analysis platform PathSight, to dig into his data on recurring sales killer trends:

Today's Revenue/GTM Leader Speaker:

• Mike Hoffman
• CEO and Co-founder of PastSight
• mike@pastsight.com
• Co-Head Chapter, Pavilion - NYC Chapter

It's Not Your Product. It's How You Sell It.

After parsing insights from hundreds of customer interviews, Mike surprisingly found product rarely was the reason why deals closed lost.

Instead, deals hinged on effectively selling value - which begins by deeply understanding each buyer's unique pain points and decision criteria beyond ROI.

Without that insight, reps push generic pitches that fail to land. And they leave enterprise deals exposed to eleventh-hour attacks from savvier competitors.

As Mike said, there's "so much more within a sales team's control than they think." So before crying for more features, fix the selling first.

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Lead With Insight and Kindness

Looking inward, Mike realized even experts slip on Sales 101 when actually grinding in deals daily. As he put it, there's "more empathy, probably, than I did."

So for 2024, he's doubling down on consistency - following structured processes, meticulous discovery questions, prompt follow-ups. Mastering the basics breeds results.

He's also determined to lead with compassion, making genuine connections and kindness top priority even when stressed or outcomes disappoint.

Lifting others lifts revenue too over the long run. And it's the right thing to do.

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Get Back to Basics

When everything gets noisier amid economic uncertainty, creatively standing out matters more than ever according to Mike.

Rather than one more cold call, he suggests reimagining go-to-market completely through avenues like events and communities.

Ultimately, real relationships triumph over transactions. And back-to-basics execution beats flailing for silver bullet hacks.

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To Recap

If deals keep dying on the vine, take an honest look at selling skills before blaming product - then get to work.

Strengthen foundations and lead with care. The smallest shifts net big returns as markets rebound.

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Giving Back to the Community

What Mike Hoffman can do for you

Looking for a job in sales? Mike Hoffman would be happy to help point you in the right direction! He's helped 7-8 people get jobs last year with at least 2 people he knows. Helping the sales community brings him joy. 💙

What you can do for Mike Hoffman

Referrals! Connect Mike Hoffman with any revenue leaders that are interested in win-loss analysis and see how they can take their revenue teams to the next level.

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About Recapping with Recapped 🎯

Recapped CEO Mark Fershteyn interviews and unpacks the critical lessons learned by top revenue and GTM leaders in 2023. This series dives deep into their insights, strategies, and hidden tactics, offering you the blueprint to dominate 2024.

Recapped believes in the power of knowledge sharing. We're passionate about amplifying the voices of these industry leaders and helping their insights reach a wider audience. Learned something? Share this page with others, you're not just gaining valuable knowledge – you're becoming part of a community dedicated to pushing the boundaries of revenue excellence.

‍Apply to interview for our Recapping with Recapped series by emailing explore@recapped.io.