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Why Hasn’t the B2B Sales Playbook Changed?


Nate Nasralla (Fluint), Rachel Shi (Metadata), and Mark Kosoglow (Formerly Catalyst Software) share their theories on why the sales playbooks in 2024 are still lagging, and the ways they’re changing the game within their own organizations.

What’s working in B2B selling


Kobe took tap dancing lessons to strengthen his ankles. Arnold Schwarzenegger took ballet lessons to learn how to pose onstage. Going outside of your discipline gives you a better perspective and helps break tired plays.

What’s not working in B2B selling


”Hey, what are the 3 biggest problems you’re facing right now?” – ask that, and your prospect is already zoned out. It’s time to find new tactics that will engage and impress as a first impression.

The key takeaways

  • Tailor your training: Rachel Shi underscored the importance of moving away from a one-size-fits-all model of sales training to a more tailored approach that addresses the nuances of B2B SaaS. B2B marketers should assess the specific needs of their sales team and customize their training programs to improve effectiveness.
  • Speak your buyer’s language: Rachel, Nate Nasralla, and Mark Kosoglow emphasized the significance of understanding and using the buyer’s language within business cases and sales conversations. Marketers should ensure that sales tools and materials resonate with their target audience by aligning them with the buyer’s internal terminology and perspective.
  • The power of polarizing questions: The guest panel discussed the strategic approach of using polarizing questions early in the sales process to identify qualified prospects and position solutions effectively. Marketers should consider developing materials that assist the sales team in deploying these questions to uncover key customer pain points and motivations.
  • Prioritizing empathy and relationships: Nate highlighted that empathic accuracy is imperative for building genuine sales relationships, but it’s often lacking. Marketers must foster an empathetic understanding of their potential buyers to craft campaigns and messaging that resonate on a human level.
  • Embrace the deeper discovery: Nate and Mark discussed the importance of engaging buyers with deep, pattern-breaking questions. Marketers should go beyond surface-level insights and leverage storytelling and illustrative examples in their strategies to provoke thoughtful buyer engagement and uncover the true drivers of purchase decisions.

The things to listen for

00:00 Sales reps trained poorly in industrialized model

05:11 Building relationships requires understanding and empathic accuracy

08:58 Reps need mindset shift for effective sales

11:50 Rachel, do you do commission pieces? Summary: Discussion about sales and diversity in selling

15:24 Evaluating mental effort and fatigue throughout the day

18:38 System two thinking in complex deal dynamics

21:01 Engage individually, personalize outreach and follow-ups

26:13 Building business cases requires deep discovery conversations

29:59 Emphasize positioning, change, and asking effective questions

33:47 Clarify objections, redo role play to assess

36:45 Applicants share unique opinions and personal projects

40:32 Using written content helps shave sales time

41:26 Creating message together, internalized value in writing

45:26 Diving deep into buyer’s language for solutions

48:29 Remember seeing Rachel’s old business case

51:34 “Thanks for having us, of course.”

The recap

Rachel Shi got us thinking with her take on why some sales reps might as well be trying to sell with one arm tied behind their backs – hint: it’s all about the training. Nate Nasralla wasn’t shy about calling out the elephant in the room – leadership, or the lack of it, which is causing a cycle of ‘meh’ in sales mentoring.

And let’s not forget Mark Kosoglow’s trip down memory lane, teaching us a thing or two about how selling shoes taught him the magic of tuning into customer needs. The gang tackled empathic accuracy – a fancy term that basically means understanding your peeps, and hilariously, they played a round of ‘guess the average level’ with ‘Price is Right’ flair.

Nate dropped a bomb on us revealing that most deals are running around like headless chickens without a solid business case – yikes! He’s got a fix, though: Talk the buyer’s talk, and keep things tight and bright with a killer one-pager.

Ever wondered how to make your pitch stick like gum on a shoe? The crew shared secret sauces, like finding those sneaky internal phrases, storytelling to wake up buyer’s brains, and spicing things up with polarizing questions. Job interviews in sales? They chat about why it’s less about ‘What’s your biggest weakness?’ and more about ‘Show me you can learn and hustle.’

Zoom culture, observation skills nabbed from the design world (props to Rachel), and the mind-game tango between system one and system two thinking also made the cut. Navigating sales is not just about selling; it’s also about reading the room like a best-selling novel, making champions out of clients, and all that behind-the-scenes drama you never see on LinkedIn.

In a nutshell, this episode isn’t just another sales strategy sermon – it’s a treasure chest of what it really takes to make it in the B2B SaaS sales world, with a side of real talk and a few laughs. Don’t miss it. Seriously, tune in and get your sales game face on this episode of The Proof Point.

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