Insight-Driven Outreach Beats Personalization with Ana Leyva - Ep 51

Plus, Scaling Beyond Your Founder-Led Sales Motion

Apr 19, 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

Who would have thought that we’d be able to keep this little podcast on the rails (for the most part) for 50 51 episodes? Well, enough of the sappy crap, let’s get into the good stuff.

Also, allegedly, Craig has been “too busy” doing his actual job, prepping for some ‘go-to-market summit’ thing, to send Producer Sam anything for this edition, so welcome to Sam’s 26-year-old Marketer Newsletter 2: Electric Boogaloo.

Here’s what’s on deck this week:

What ~~Craig’s~~ Sam’s Reading & Watching
Recent Insights from Past Guests
This Week’s Movie Poster Mock Up
Latest Episode: Insight-Driven Outreach Beats Personalization with Ana Leyva - Ep 51

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

What Sam’s Reading & Watching

First up, I’ve been a big fan of Jen Allen-Knuth for a few years now, back to when she was still at Challenger. She’s a great follow for sales and messaging tips, like this recent post about crafting more impactful follow up messages for ‘those deals that have stuck around since last quarter.’ She highlights the problem with most of these messages that sellers send to ‘check in’, and she gives a great example of how to flip things around by hypothesizing why the deal might be stuck and still provide long-term value to the buyer.

Read Jen's Post

Second up, as a marketing major on the East Coast, I didn’t have any real exposure to the tech/startup/VC world until a few years ago. So, aside from being thrown into it by working with a bunch of B2B SaaS startups and consuming a lot of podcasts, I’ve really started to understand the landscape much better, thanks to videos like these from Dan Toomey at Good Work (Part of Morning Brew). Is my knowledge of how Silicon Valley works actually based on these videos? No. However, I think they’re funny and I don’t have anyone else to share them with. Enjoy.

What VCs actually do:

Third up, I’ve been loving the AICMO video podcast series that Bruno Bertini’s been doing for the past few weeks. Bruno, the CMO of 8x8 co-hosts this short-form podcast with AI CMO, aka: ChatGPT. I think it’s an intriguing format, generates interesting content, and is excellently put together.

Episode 1: Intro to the Series
Episode 2: Improving your “AIQ” & Driving Change
Episode 3: Merging Performance with Creative & Brand as a Marketing Leader
Episode 4: How AI can co-exist with Creativity
Episode 5: How AI shifts Demand Gen from Reactive to Predictive

Recent Insights from Past Guests

Sam McKenna, Sam’s Episode of The Transaction

We’ve all been there, you join a sales call and the buyer isn’t fully there… The instinct is to be accommodating, which is a great way to garner even less of their attention. I love Sam’s take on how you should respond in these situations to judo-flip the conversation on its head. Sams have to stick together.

Read Sam's Post

Jon Miller, Jon’s Episode of The Transaction

Wait, let me get this straight, a video with a cocktail recipe and an interesting take on 1:1 personalization delivered by one of the marketing greats? Say no more.

*“The idea was good, but the technology wasn’t ready” - Jon said the same thing in a review of the CGI for Dwayne The Rock Johnson’s Scorpion King in The Mummy Returns (Sommers, 2001)*

Enjoy Jon's Post

Latest Episode: Insight-Driven Outreach Beats Personalization with Ana Leyva - Ep 51

Ana Leyva advises early-stage startups at Pear VC on their go-to-market strategy to help them build stunning sales motions that set them up to scale. Ana provides pre-seed and seed startups with her first-hand experience as a seasoned operator with past roles at tech unicorns Box, ServiceTitan, and Vanta. Ana joins Co-Hosts Craig Rosenberg and Matt Amundson to delve into how to transition beyond a founder-led sales motion without losing their special perspective, why insight-driven outreach beats crappy sales personalization in B2B, and the two foundational pillars that you need to have in place to build a strong go-to-market strategy.

Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company.

Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter.

Critical Takeaways

The crappy bit of personalization you grabbed from LinkedIn and added to your stale cold outbound email is not going to set you apart. ‘We went to the same school’ doesn’t help that decision maker develop a solution to the problems they’re facing.
Rather than relying on bare-minimum ‘personalization’, put your thinking cap on and reach out with a business insight that can actually help your prospect learn more about their business, understand their problem better, or make a more informed decision.
As hard as it can seem to turn down customers early on, founders need the discipline to focus on prospects who will truly benefit from their product, and saying no to the wrong fit is crucial for building long-term customer relationships.
The bedrock of your go to market strategy should be built upon endless customer obsession and very strict ICP (Ideal Customer Profile) parameters. That ensures you deeply understand the pain your customer solves and can build a product to solve that pain effectively.
Don’t just let your customers come to you, you need to pick the right protagonists for the epic narrative that you are creating for yourself and your customers. Be picky about who you allow to join and steer the arc of this grand story you are embarking on.

Epic Quotes

“I am sick of personalized emails.” - Ana Leyva
“I always tell our founders, you’re not selling for the initial close; you’re selling for the renewal.” - Ana Leyva

Connect with Ana

LinkedIn: https://www.linkedin.com/in/analeyva/
Pear VC Website: https://pear.vc/

Shoutouts

AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/
Brandon Redlinger: https://www.linkedin.com/in/brandonredlinger/
Brent Adamson: https://www.linkedin.com/in/brentadamson/
Brent’s Episode
Chris Orlob: https://www.linkedin.com/in/chrisorlob/
Chris’s Episode
Jen Allen-Knuth: https://www.linkedin.com/in/demandjen1/
Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/
Jason’s Post on LinkedIn: https://www.linkedin.com/posts/jasonmlemkin_so-theres-a-lot-of-angst-on-linkedin-about-activity-7308223252420509697-EJCS
Stevie Case: https://www.linkedin.com/in/steviecase/
Scott Albro: https://www.linkedin.com/in/scottalbro/
Gong
Scott Barker: https://www.linkedin.com/in/ssbarker/
Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/

This Week’s Movie Poster Mock Up: Lethal Weapon

Based on the resounding silence of the feedback created by last week’s poster of Craig and Matt’s stylized faces plastered onto a classic movie’s poster, we’ve decided to double down out of spite.

It’s amazing what you’re able to accomplish when you’re motivated by spite.

Anyway, here you are. Enjoy.

Love the show? Give us a shoutout on LinkedIn and tell us what you loved! Conversely, hate the show? Email Sam.

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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