In this episode of The Pennock Knockdown, host Nikki Pennock is joined by Jason Berkowitz, founder and CEO of the SEO agency Break the Web. With over 15 years in SEO, Jason brings a practical perspective to the most turbulent year in search history.
Jason shares his origin story, from studying physical therapy to stumbling into SEO by trying to rank for "personal trainer NYC". This led to a freelance career and the 2017 launch of Break the Web—a name conceived after "a little too much whiskey".
Jason breaks down his agency's philosophy, built for in-house DTC marketing teams. He aims to make SEO "less annoying, more measurable, [and] accessible" with a 12-month strategic roadmap. The process starts with foundational technical SEO and UX, then moves to keyword research (informational vs. transactional intent), on-page SEO, and finally, off-page digital PR for high-quality backlinks.
The conversation pivots to AI's disruption of search. Jason confirms Google's AI Overviews have "taken tons and tons of clicks" from top-of-funnel content. While impressions are up, clicks are down. His strategic response is to focus on mid-bottom-of-the-funnel content. He shares an example of an ultra-high-net-worth client (products start at $100k) for whom they advised against a traditional blog strategy, as their persona "know what they want".
If blogging is on shaky ground, where should brands focus? Jason argues that Schema markup is "more powerful... than it's ever been". It powers rich snippets in traditional search (star ratings, price) to increase clicks and provides clean, structured data for AI bots, which "could only help". While hard data on AI impact is "inconclusive," he insists it's essential foundational SEO.
How can brands track this new AI landscape? Jason discusses new tools like Profound and SEMrush's AI tracking feature, and reveals his team built their own internal tool to track brand mentions within AI prompts.
This leads to a discussion on agency life. Jason defines two types of SEO agencies: those brilliant at SEO but "stink at communication," and those great at communication but "kind of suck on the SEO delivery side". His goal is to "bridge that gap".
Finally, Jason shares his top advice for leaders. His productivity hacks: segment your day and be strict with your calendar—"if it's not in your calendar, it doesn't exist". His advice to his 2010 self? Get mentorship earlier and learn to delegate sooner.
Key Moments & Timestamps:
00:00:30 Jason's Origin Story: How a physical therapy student and personal trainer discovered a passion for SEO 15 years ago.
00:01:50 The "Break the Web" Rebrand: The whiskey-fueled story behind the agency's name.
00:04:06 A 12-Month SEO Roadmap: Jason details his agency's process, from technical foundations to digital PR and link-building.
00:05:15 The Impact of AI Overviews: How AI is "taking tons and tons of clicks" from top-of-funnel content.
00:06:43 When Not to Write Blog Content: The case of a $100k+ product and why their customers aren't browsing informational queries.
00:07:38 Why Schema Markup is More Powerful Than Ever: Its dual benefit for traditional search (rich snippets) and AEO (AI understanding).
00:09:40 Is AI Killing Your Traffic? Analyzing the split between rising impressions and falling clicks.
00:12:17 How to Start Tracking Your Brand's AI (AEO) Mentions: A look at new tools like SEMrush and building your own.
00:13:29 The Two Types of SEO Agencies: How to bridge the gap between technical expertise and client communication.
00:15:37 There is No "Foolproof Framework" for AEO: Why the best AEO strategy right now is just "great foundational SEO".
00:19:57 Productivity Hacks for Agency Owners: The power of a strict calendar and segmenting your day.
00:23:06 Advice to His 2010 Self: Get a mentor and delegate sooner.
00:24:23 How to Connect: Find Jason and his team at BreakTheWeb.agency.