Insight-Driven Outreach Beats Personalization with Ana Leyva, Go-To-Market Advisor at Pear VC

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The Transaction

Craig Rosenberg & Matt Amundson | B2B Sales & Marketing Experts - Hosts of The Transaction

72 episodes

21 hours ago

Welcome to The Transaction. The #1 Go-To-Market podcast on the planet. Hosts Craig Rosenberg and Matt Amundson, two legendary go-to-market leaders in their own right, talk weekly with the best sales, marketing, operations, and product leaders in the B2B SaaS world to understand what's working in the new playbook of the post-ZIRP market. But Craig, Matt, and their guests don't just talk theoretically, they share the stories and actionable tips, tactics, and strategies behind what's driving revenue growth that you can take and implement in your own go-to-market roles. Whether you're a Chief Revenue Officer leading a B2B SaaS sales and marketing organization, a marketing leader trying to drive bigger outcomes with your demand gen team, or a new sales rep, you'll learn and laugh every episode. From ABM to PLG, from MEDDIC to MEDDPICC, the world of business is constantly evolving. We’ll cover the who, what, where, when, why and most importantly how you get… The Transaction. About Your Hosts Craig Rosenberg is the Chief Platform Officer at Scale Venture Partners. He is a seasoned expert in B2B revenue growth, helping SaaS companies transition from founder-led growth to becoming high-growth Go-To-Market machines. Previously, Craig was a Distinguished VP Analyst at Gartner and co-founder of TOPO Inc., a research and advisory firm acquired by Gartner in 2020. Craig thinks Die Hard is a Christmas movie. Matt Amundson is the Chief Marketing Officer of DuploCloud. He is also an advisor for companies such as Sendoso and Salesloft. Prior to DuploCloud, Matt spent time as an Executive In Residence with Scale Venture Partners and led marketing departments at Census, Very Good Security, and Everstring, to name a few. Matt thinks Die Hard 2 is better than Die Hard. The Transaction is produced by Sam Guertin.

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Insight-Driven Outreach Beats Personalization with Ana Leyva, Go-To-Market Advisor at Pear VC - Ep 51

The Transaction

52 minutes

6 months ago

Insight-Driven Outreach Beats Personalization with Ana Leyva, Go-To-Market Advisor at Pear VC - 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.

Sponsored Segment

Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com

Chapters

00:00 - Episode Preview

00:20 - Squishy Pineapples & The 1995 UCLA Bruins

04:01 - Introducing Ana Leyva, GTM Leader at Pear VC

08:29 Selling at B2B Conferences on the Road as a New Mom

11:32 - Focus on Providing Value, not on Bland “Personalization”

21:33 - B2B SaaS Founders Need to Rewrite New Go To Market Playbooks

27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales

34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup

45:06 - Is Cold-Calling Coming back in Style for SaaS Sales Teams?

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/

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