Social Selling Secrets to Supercharge Your Sales with Sam McKenna - Ep. 48

Plus, What are Your WORST Webinar fails?

Mar 28, 2025

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

Well, that was a quick Q1…

No matter how you’re numbers turned out, we’ve got some great stuff this week to help you kick last quarters ass in Q2 (Or give you a laugh if you’ve got a lot of free time because you had a less than optimal Q1).

Here’s what’s on deck this week:

What Craig’s Reading x2
Recent Insights from Past Guests: Scott Albro + David Politis
Latest Episode: Social Selling Secrets to Supercharge Your Sales with Sam McKenna - Ep. 48

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

What Craig’s Reading: The Valley LinkedIn Playbook via Zayd Syed Ali

Right now, the best examples of GTM innovation are coming from startups. Growth hacker mindsets are creating new plays…and they work. This piece has a lot of great ideas.

Read Zayd's Piece

What Craig’s Also Reading: The 11x Scandal

Well, salestech has to make the news somehow. I have a secret: a lot of startups do what they did. The accounting irregularities? No, don’t do that. The fake customer logos, a three-month out on your annual contract, etc. This happens all the time.

Recent Insights from Past Guests

Scott Albro (speaking of the 11x controversy)

Scott's Post

Scott's Episode

David Politis (his new show has great founder insights)

David's Post

David's Episode

Latest Episode: Social Selling Secrets to Supercharge Your Sales with Sam McKenna - Ep. 48

It’s painfully pitiful what passes as personalized prospecting presently. However, we’ve got just the guest to help sales reps get back on the right track.

Sam McKenna is the Founder of SamSales Consulting and is the foremost expert on social selling and leveraging LinkedIn to drive revenue. Sam and her team are redefining the go-to-market status quo for modern organizations through unmatched sales training and LinkedIn branding. Sam joins co-hosts Craig Rosenberg and Matt Amundson for a very fun and fascinating dive into how to improve your personalized sales messages to prospects, the secrets to successful social selling, and the best time to prospect. Plus, we share stories from some of our worst webinar fails.

Also, Craig denies claims that he was in fact the heavy breather while hosting a webinar with Guy Kawasaki a decade ago and Matt reveals the truth about the size of a certain actor’s mouth.

Critical Takeaways

Sales reps, please take 3 seconds to THINK before sending another stinky, smelly, no-good, automated email to a prospect. If you want to stand out to them and get their attention, earn it by doing the work that none of the other reps reaching out to them won’t. Show them you know them.
A simple way to stand out to decision makers at target accounts is to engage with their LinkedIn posts. However, hitting “like” does not qualify as engaging in a way that will stand out. The smart play is to comment something insightful.
Prospecting during non-working hours, like weekends and evenings, can capture the attention of busy executives. Emails sent during these times can stand out because prospects are usually less overwhelmed and more likely to engage with content beyond their regular work distractions.
Don’t buy a ‘great new tool’ until you know what you’re going to do with it. Figure out how to solve the problem you’re addressing before you ever get close to buying a tech solution.

Chapters

00:00 Intro Sales Insights with Sam McKenna
04:38 Introducing Sam McKenna, Founder of SamSales Consulting
08:02 Announcing The New Sam McKenna Award For The Best Guest
10:13 A Particularly Titillating LinkedIn Controversy
11:44 The Airing of Our Webinar Woes
22:41 Companies Suck at Solving Problems & Try to Techstack Their Way Out of Issues
28:50 How to Run the “Been Awhile” B2B Prospecting Play using LinkedIn Sales Navigator
30:24 How to Use Social Selling in SaaS
34:40 Spearfishing for B2B Leads Using This Tactic on LinkedIn Sales Navigator
41:44 Why Putting in the Work is the Way to Wow Prospects and Customers
45:50 Why the "Show Me You Know Me" Method Works so Well for B2B Sales Reps

Epic Quotes

“ Why is it that so few people will just put in the actual work that that converts?” - Sam McKenna
“ Make the effort.” - Sam McKenna
“Don’t air any of this.” - Sam McKenna

“ Anything that you can't automate won't be done.” - Matt Amundson

Connect with Sam

LinkedIn: https://www.linkedin.com/in/samsalesli/
Website: https://www.samsalesconsulting.com/
Sam’s new Podcast: https://www.samsalesconsulting.com/showmeyoukknowmeshow/

Shoutouts

Hayley Hoad: https://www.linkedin.com/in/hayley-hoad-2565549/
Bobby Axelrod (Billions)
Jill Rowley: https://www.linkedin.com/in/jillrowley/
Paige Tills: https://www.linkedin.com/in/paige-tills/
Joy Wilder Lybeer: https://www.linkedin.com/in/joywilderlybeer/
Gail Moody-Byrd: https://www.linkedin.com/in/gailmoodybyrd/
Adam Robinson: https://www.linkedin.com/in/retentionadam/
Adam’s episode of The Transaction: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal
Toby Carrington: https://www.linkedin.com/in/tobycarrington/
DocuSign
ON24
Marketo
Engagio
Guy Kawasaki: https://www.linkedin.com/in/guykawasaki/
Jon Gray: https://www.linkedin.com/in/jon-d-gray/
DailyMail Article about the “LinkedIn Boobs Post”: https://www.dailymail.co.uk/news/article-14406563/linkedin-post-fury-comparing-woman-breast-size-confidence.html
Bobby Axelrod/Damian Lewis Tiny Mouth Investigation: https://www.maxim.com/entertainment/damian-lewis-tiny-mouth-2016-3/
Reddit discussion of Bobby Axelrod/Damian Lewis’s tiny mouth: https://www.reddit.com/r/Billions/comments/8jcnx5/anyone_else_getting_annoyed_by_damian_lewis_tiny/

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Follow the Hosts

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

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