Reading · The Transaction

Welcome to the latest weekly edition of The Transaction newsletter & podcast. Every Thursday, we share resources you should check out, what we’ve found insightful recently, and tactical ways you can improve your go-to-market today. For more: Podcast | YouTube

Really feeling an emptiness since the world cup ended… On the upside, however, there’s a lot less dual screening to be done (until NFL pre-season kickoffs… Oh, the HOF game is only 16 days away… Splendid.)

Here’s what’s on deck this week:

What Craig’s ~~Reading~~ Shamelessly Self-Promoting
Recent Insight from Past Guests
Latest Episode: How Founder POV Helps Sales Build Buyer Confidence with Jim Wilson - Ep 84
Movie Poster Mockup: The Odd Couple (Gene Saks, 1968)

Did someone forward you this newsletter? I’m sorry about that, but since you’re here, you might as well subscribe…

I hate putting my own posts in the “what Craig’s reading” section but well, I am. This came from my presentation at Jen Igartua’s (past guest) RevFest. RevFest is the best show I go to each year. My keynote was inspired by a memo from Scale Venture Partners investor Max Abram.

Jim Wilson is an Operating Partner at Costanoa Ventures and cut his teeth leading global sales teams for decades at major companies including SumoLogic, Microsoft, Merced Systems, PTC, and NICE Systems.

Jim joined Co-Hosts Craig Rosenberg and Matt Amundson to discuss the impact that strong Founder vision has on the sales team’s narrative, why paid POCs (Proof of Concepts) are making a comeback in B2B sales, and what truly sets B2B events apart for buyers.

Plus, Jim examines why corporate gifting swag has gotten so bland while also providing some great examples from B2B brands that are doing it well.

Also, Craig reads verbatim from the article of a past guest, Matt extolls the virtues of the loop-swoop-pull technique, and Producer Sam shouts out a fellow Sam.

Develop and weaponize a strong founder point of view, and then cascade it to sales. The single biggest differentiator in a crowded market is a bold, opinionated narrative that challenges the status quo.
Train sales reps to lead with a prescriptive point of view on how to evaluate your product. Rather than asking prospects “what do you want to do next?”, top reps proactively outline a logical, step-by-step evaluation process. Top B2B sellers consistently become trusted advisors by doing this, which ultimately means they are invited to help prospects draft the RFP and frame competitors.
B2B events are producing outsized pipeline, especially intimate dinners of 10–12 people. The key rule: no structured pitches, no selling at the event itself. Rather, use the event to learn where prospects went to school, what their kids are up to, and what makes them laugh; then follow up the next day with a warm, specific outreach.
Implement paid, time-boxed POCs with both technical and business validation built in to validate not just technical fit but business ROI. Stop running open-ended “kick the tires” evaluations with no end date; set a timeline, assign a kickoff call, schedule the readout with decision-makers, and build a report that champions can use to get internal approvals.
When it comes to effectively planning events and corporate gifting, GTM teams should ask: what does our buyer persona find genuinely interesting, and how do we build an experience around that?

00:00 - Episode Preview
02:25 - Introducing Jim Wilson, Partner at Costanoa Ventures
05:57 - Why Creativity is Key to Effective Corporate Swag
13:27 - A Disastrous First Encounter with a Bidet & Other Sleepy Sales Stories
22:42 - How a Strong Founder POV Helps Sales Teams Build a Narrative
33:36 - Events are Back as a Major GTM Channel
45:09 - Why Paid Proof of Concepts are Comin Back in B2B Sales Cycles

“ I love sales teams that have a strong point of view on how you should evaluate our product.” - Jim Wilson

LinkedIn: https://www.linkedin.com/in/jimwilsonbayarea/
Costanoa Ventures Website: https://www.costanoa.vc/

Carilu Dietrich: https://open.substack.com/pub/thetransaction/p/advisor-avengers-assembling-your
Business Bricks: https://businessbricks.com/
Maria Boulden: https://open.substack.com/pub/thetransaction/p/steak-dinners-dont-close-deals-with
Sam McKenna: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge
Brian Halligan: https://www.linkedin.com/in/brianhalligan/
Chris Orlob: https://open.substack.com/pub/thetransaction/p/solving-the-go-to-market-skills-crisis
Scott Albro: https://open.substack.com/pub/thetransaction/p/founder-led-gtm-growth-bets-and-why
David DMo Morse: https://www.linkedin.com/in/yodavidmorse/
Topline: https://substack.com/@toplinemedia
Craig’s Article for Topline about Driving Demand:

Omar Akhtar: https://open.substack.com/pub/thetransaction/p/how-the-most-successful-b2b-marketing
David Politis: https://open.substack.com/pub/thetransaction/p/narrow-down-your-damn-icp-with-david
Joe Sullivan: https://www.linkedin.com/in/joesu11ivan/
Robert Koehler: https://www.linkedin.com/in/rkoehler/
Bugcrowd: https://www.bugcrowd.com/
Feldera: https://www.feldera.com/

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Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/

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How Founder POV Helps Sales Build Buyer Confidence with Jim Wilson, Partner at Costanoa Ventures - Ep 84

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