How to sell when you are being squeezed from both sides

Dr. Strangebot: How I learned to stop worrying and love Agentic AI

Does agentic AI pose an existential threat to B2B Sales, or is it an Iron Man™ suit that gives us super revenue generation powers? This week we dig into Yasar Yilmaz’s compelling thesis on Agentic AI & the future of Sofware Sales. Will AI agents take over core selling functions like opportunity qualification and deal progression, and is this a good thing, or  is it the beginning of the end of what we know of our roles and value? Or is it only the end of the beginning? Bonus material: Road tripping with Bill Murray and Ryan Reynolds

Selling your way out of Sales Purgatory

This week we take on the painful and common problem of how to sell and market to those who love our products, but still do not buy.  This is the tech win/business loss conundrum that takes up far too big of a piece of any given fiscal year’s pipeline. Join us for some ideas on how to uplevel your execution to either avoid or win more often in these situations. Bonus: Jake creates a tie.

Two Decades Worth of Sales Advice | Our Interview w/Yosh Eisbart

Everybody BEHAVE! We have a GUEST! In celebration of our 30th episode, we welcome 3-time co-founder & Saas scaler, 2-time published author, and 1 time brother of Jake: Yosh Eisbart, VP of Sales for VASS Solutions.   In this power packed 45 mins, Yosh shares his insights on the importance of thought leadership, leveraging referrals as a core demand gen driver, and what to look for when building your sales team.   Bonus Track: Who would you rather Vice Versa with: Michael Jordan or Yo Yo Ma?

It's time to have "the conversation" with your prospects.

The US Dollar and consumer confidence are down. A recession is most likely coming. Higher inflation looms and the new Superman movie looks like...well not great.   These aren't nice things to say or hear...but maybe that's EXACTLY why they need to be said and heard.  Join us on this week's episode of YBT where we take a page from the Dutch playbook...Be direct, be honest and address the elephant in the room head on. Bonus material: Who builds more pipeline, a Jedi or a scoundrel?

How to sell when you are being squeezed from both sides

The buy-side wants price relief, the sell-side wants higher margins…and we want to hit our numbers. Are we now selling into the perfect storm, with budgets on shifting sands and SaaS company margins under unexpected pressure…maybe…no wait? Through all of this uncertainty, we have to get more creative than usual. On this week’s episode Jake and I dive into the importance of face time and partnerships when the skies start to darken, and walking the tightrope of selling both near term returns to secure budgets while selling long term returns to maximize TCV…kind of like asking a receiver to go short and long at the same time. Join us for some shelter from the storm and ideas for weathering it. Bonus material: When is a cave a preferred living arrangement?