What I learned from pitching a top Enterprise seller

Hey there 👋 it’s Dec 23rd … are you still in the trenches pushing DocuSign reminders? Trying to get that last deal closed?

Wishing everyone a very happy holiday season. ESPECIALLY to those brave souls fighting to close deals until Dec 31st at midnight. I believe in you 🫡

As a reminder this newsletter is effectively my journal to better understand & elevate the craft of Sales. Thank you for joining me on this journey.

Inside today’s edition:

• How I got ripped apart by a top enterprise seller + what I learned

• Elite Sales Recruiter: “The #1 in-demand skillset is Curiosity”

• Why Qualification is the top priority for SDR teams right now

Let’s dive in 👉

What a top enterprise seller had to teach me about Sales

I had the worst, best sales call the other day. I say it’s the worst because I got schooled. But it was also the best because he gave me the greatest gift: direct, actionable, and generous feedback.

Here are the top 3 pieces of feedback I took away:

1. When a prospect fits your ICP, make sure they KNOW IT.

   His company perfectly fit our ICP. But I never told him that.

   Your prospect should feel as though the product was made with them in mind. That out of ALL the 1,000+ AI sales products, this just so happens to be the AI sales product built precisely for him. And I missed that opportunity. It won’t happen again.

   My New Mental Model: In Formula 1 racing 🏎️, each car costs ~$15M and is built with the body shape of the driver in mind. When I can, tell each prospect that my product (the Formula 1 race car) was built specifically for them.

2. When selling to the Enterprise, look for PERSONALITY OVER TITLES

   When prospecting for an enterprise-size deal ... it matters less what the individual's title is. What matters more is the personality of that individual.

   Is my champion still upwardly mobile in their career? Or are they settling down in their personal life and looking to de-risk? How comfortable will they be in taking on the risk to work with new vendors? These are the questions to answer.

   My New Mental Model: Can I see this person skydiving? 🪂 If yes, there’s a good chance they’ll be open to a new vendor. If no, proceed with healthy skepticism.

3. Make EVERY MINUTE COUNT

   Towards the end of the demo, I transitioned to show a feature that didn’t address his core pain. He kindly asked if I thought this was the best use of time, or if we should focus elsewhere.

   In a tight 30min demo, you want to maximize the value from every minute - both for you and the prospect. You can’t afford to spend that time carelessly.

   My New Mental Model: the average 30second Super Bowl ad costs $7M 📺️. Each minute of my demo is also expensive airtime. Would you spend that precious airtime showing something irrelevant to your prospect?

My main takeaway from this conversation was a reminder that sales done right is true art. It requires a radical level of care, preparation, and dedication to your craft. The result is the best outcome for your buyer, and for you. THAT is what I’m searching for.

Elite Sales Recruiter: “The #1 in-demand skillset I’m hearing is Curiosity”

For those that aren’t familiar, Jake Citrano and his cofounder Jay Green are two of the top Sales Recruiters in early-stage B2B software. Both are elite at their craft, and both freely share their insights on LinkedIn to help sales reps successfully navigate their career decisions.

Together they run ClosedWon Talent and Quota Hunters … and I had the opportunity to interview Jake about the job market for sales talent heading into 2025.

As someone on a journey to develop their own sales skillset, I wanted to ask Jake what the most in-demand skillsets from hiring managers are. Is it natural closing ability? The ability to write good sales emails with ChatGPT? Or something else??? His answer:

Especially for early-stage startups, Jake mentioned he’s being asked to help them hire candidates who spike on curiosity. What they’re looking for are candidates who will go above-and-beyond in understanding their buyers.

That means finding reps who are motivated by a true and powerful desire to understand the person they’re talking to, and the market they’re operating in. The type of curiosity that compels a rep to ask that extra follow-up question…which may just be the difference between a closed-lost and closed-won deal.

This conversation was full of good nuggets. More coming soon 👀

Why 7/10 SDR leaders shared that “Qualification” is their top priority in Q4

Speaking of curiosity … when I hear the same challenge come up multiple times from prospects, I get curious. But if that same challenge is mentioned on 7/10 calls? I get VERY CURIOUS.

Last week something strange happened. 7/10 VPs & Directors of SDR/BDRs all said the same thing. The thing they’re being pushed hardest on for next quarter is QUALIFICATION.

They shared that in almost all cases - the push for Q1-Q3 was volume, volume, volume. More net-new prospects, more calls, more emails. And they often had to do this with FEWER SDRs.

But this quarter is different. The game in Q4 has shifted from volume to qualification. The push I’m hearing is: “How do I help my reps continue to hit & exceed quota, given these new qualification requirements? This level of qualification means a 1-call book is unlikely. We need to figure out how to maintain outputs (already hard), and with a higher qualification standard (mega hard)”.

That means more coaching on how to run effective follow-up calls, how to ask for BANT and related questions, and proper task tracking to ensure tight follow-ups.

Jameel Rehman over at Tech Sales Academy said it best: “Great qualification has always been the lynchpin for great sales.” The best sales teams not only generate more pipeline, but they also convert a higher % of their pipeline into closed-won deals.

So what’s the best way to do this? I’m going to find out. I’ll be diving into this more in coming Salescraft editions … but I’m also curious for your feedback. How have you seen sales teams effectively tighten qualification? And doing this while keeping the SDR team motivated + pipeline flowing?

Please let me know if if anything in this edition resonated! And as always, ideas / questions / feedback / rants are all welcome. It’s what I’m here for 😃

-Ross

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