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

52:18 Apr 19, 2025
About this episode
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 TakeawaysThe 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 SegmentInterested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.comChapters00:00 - Episode Preview00:20 - Squishy Pineapples & The 1995 UCLA Bruins04:01 - Introducing Ana Leyva, GTM Leader at Pear VC08:29 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 Playbooks27:24 - Scaling Yo
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