In 1998, asking a search engine for anything useful felt a little like consulting an oracle with poor hearing. The web was unruly, the results were erratic, and respectable advertising people still had plenty of other places to spend their money. Jeffrey Herzog looked at this confusion and saw a market. He founded iCrossing around the proposition that a company could deliberately improve where and how it appeared when someone went looking.
It is easy to make that insight sound obvious from the polished side of history. It was not. Google had only just been incorporated. Search engine optimization was closer to a craft practiced in back rooms than a line item in a global marketing budget. Herzog, an American University graduate whose degree joined communications with law, economics, and government, entered from a useful angle: he understood that visibility was never purely technical. It was also commercial, institutional, and human.
That combination became the thread through three companies and nearly three decades. iCrossing organized the first era, when search offered a page of links. ZOG Digital addressed the next one, when content and social distribution crowded the screen. Avenue Z is built for the present moment, when the screen may offer a composed answer and quietly decline to mention everyone else.
Before search had a dress code
Early iCrossing sold companies on the value of intent. A person typing a phrase into a search box was doing more than browsing. They were declaring an interest, perhaps even a need. Herzog’s phrase for the company’s DNA was “consumer interest and intent.” That idea pulled iCrossing beyond organic rankings into paid media, research, analytics, web development, mobile, and broader digital work.
The agency expanded by acquisition as well as by hiring. In the two years before 2008, Herzog and incoming chief executive Don Scales worked on five acquisitions. When Scales took the chief executive role, Herzog moved to vice chairman and kept responsibility for strategic direction. The company then counted 620 employees across 15 offices and served more than 40 Fortune 500 companies. The scale is worth pausing over: an obscure specialty had become an international agency business before social media had settled on the shape we now take for granted.
“We’ve come a long way in the past 10 years, but today feels like a new beginning.”Jeffrey Herzog, 2008
Hearst acquired iCrossing in 2010. The original announcement kept the price private, although later reporting and company accounts have supplied varying numbers. The strategic meaning was less coy. A publisher built on print had purchased a large digital marketing organization with expertise in the mechanism that was redirecting readers, customers, and advertising money.
Herzog did not retire into tasteful hobbies. In 2011 he started ZOG Digital, adding content strategy and social media to the search discipline he already knew. Investis acquired the business in 2018 and integrated it into what became Investis Digital. Herzog stayed on as a senior advisor until 2020. The second act was quieter in the public imagination than the first, but it sharpened the pattern: every new channel eventually has to answer the dull, decisive questions of distribution and proof.
Avenue Z starts with a shopping list
Avenue Z arrived publicly in 2023 with financial backing from Herzog and Baleon Capital and an appetite for parts. It bought The Snow Agency, a social and performance shop; Bevel, a communications firm with roots in technology and venture capital; and Designzillas, a digital agency in Orlando. Three acquisitions in roughly six months gave the new firm skills that would have taken years to grow one hire at a time. In 2025, Herzog bought Baleon’s remaining interest and became the full owner. In 2026, Avenue Z added Varfaj, a Shopify development and conversion specialist.
The shopping list reveals the strategy. Public relations creates credible third-party evidence. Content supplies explanation. Technical optimization makes that evidence legible to machines. Performance media buys distribution. Creators lend a human voice. Commerce closes the distance to a transaction. Each discipline can work alone, but Herzog is wagering that the joints between them now matter more than the individual pieces.
The new route to being chosen
create public evidence
interpret the record
trust, and choose
There is a neat irony here. Advertising spent years becoming more precisely measurable, while public relations guarded an aura of mystery. AI search pushes the two toward the same table. If an answer engine cites a publication, summarizes a company’s own pages, and absorbs the language used by independent creators, reputation becomes part of technical performance. The press release meets the database schema. One brings adjectives; the other would prefer labeled fields.
The answer box changes the contest
Herzog’s case for AI optimization begins with a plain change in interface. Traditional search gives the user options. An answer engine reduces those options into prose. A brand omitted from page one could still win through an ad, a review, or patient scrolling. A brand omitted from a synthetic answer may be absent from the decision entirely.
The change also scrambles a comfortable division of labor. Search specialists once concentrated on what a crawler could parse. Publicists concentrated on what an editor might print. Social teams concentrated on what a person might share. An AI answer can take signals from all three domains, then present its synthesis with the serene confidence of a maître d’ who has misplaced the reservation book. The response cannot be managed from a single desk.
This is why creators sit beside AI search in Herzog’s current argument. Machines can accelerate discovery, but a recommendation still needs a believable carrier. A specialist explaining a product on video supplies context that a banner cannot. A reported article supplies independent scrutiny that a company page cannot grant itself. A useful product page supplies the precise facts both people and systems need. The valuable unit is no longer simply a keyword or an impression. It is a corroborated claim moving across several kinds of media without changing its meaning.
His response is not to pour more copy onto the internet. It is to build a clearer public record: authoritative coverage, consistent facts, structured content, visible expertise, and enough genuine human authorship to survive the suspicion created by cheap machine-made text. In 2026, PRovoke Media included Herzog in its Innovator 25 Americas, highlighting his effort to connect earned media and content strategy with visibility inside large language model products. ADWEEK also included him in its 2026 AI Power 50.
“The shift is clear: from coverage to computation.”Jeffrey Herzog, 2026
The line is tidy, perhaps suspiciously tidy, but the idea has teeth. A magazine mention once ended as a clipping in a report. Now it may become evidence in a machine’s response to a future customer. Coverage has always affected belief. Herzog argues that it increasingly affects retrieval too.
Three companies, one recurring question
Watch what people do quietly
Herzog describes opportunity spotting with less romance than one might expect from a serial founder. Real changes, he says, begin as persistent problems. Search grew because people were overwhelmed by information. AI grows because organizations are overwhelmed by complexity. His other instruction is to watch behavior before headlines. If people keep using a rough product because it solves an urgent problem, the roughness is noise and the habit is signal.
He also likes what he calls the “plumbing” of the internet: indexing, ranking, recommendation, and the price of attention. This is an operator’s taste. Plumbing lacks glamour right up until it fails, at which point it becomes the only subject in the building. Herzog has repeatedly located his businesses near the pipes.
People who encountered him early remember the energy as much as the analysis. One former eMarketer interviewer recalled that a publicist once asked Herzog to lower the temperature before an interview because he was ordinarily so animated. Herzog later hired that interviewer at iCrossing. Another early recruit remembered meeting him socially around 2000 as the “internet guy” who persuaded him to sell search marketing for the young firm. Both stories suggest a founder for whom recruitment and persuasion were not separate activities.
“Speed without clarity is just motion.”Jeffrey Herzog, 2026
That sentence may be the best guide to Avenue Z. The company has moved quickly, but its thesis is narrow enough to repeat: brands want revenue and reputation; discovery now runs through AI systems and creator networks; the work must be integrated and measurable. Whether that produces another category-defining agency will depend on execution, particularly on proving that AI visibility changes business results rather than merely creating a fashionable new dashboard.
For Herzog, the attraction is familiar. Search in 1998 was important, awkward, and underestimated. AI answers today are important, awkward, and surrounded by extravagant claims. The technology is different. The commercial puzzle is practically an old colleague: understand where people have begun to look, learn what the system rewards, and help a company deserve to appear there.
The internet keeps changing its front door. Jeffrey Herzog has made a career of arriving while the hinges are still visible.