Didit’s Kevin Lee interviews Shay Prescott Willis, a veteran
B2B and SaaS demand generation leader, about how marketing leadership and
go-to-market strategy are changing in an AI-first world. They begin with the
rise of the fractional CMO: Shay notes that many CMOs are moving into
fractional roles as a “try before you buy” model for both executive and
company, particularly as average CMO tenure hovers around 24 months. Budget
constraints and a limited number of full-time CMO positions make fractional
work attractive, allowing leaders to step in, build pipeline and systems, and
then decide whether a full-time role makes sense.
Kevin then raises the tension between short-term results and
long-term investments, especially in private equity–owned companies with two-
to three-year time horizons. In these environments, management often
prioritizes initiatives that can move pipeline within six to twelve months (targeted
digital campaigns, event activations, demo-driving programs) over slower-burn
efforts like brand building, PR, SEO, and partnerships. Shay agrees that
pipeline and revenue targets dominate the agenda, but she also emphasizes that
long-term visibility work is becoming more important as large language models
(LLMs) change how buyers research vendors.
A central theme is preparing for this LLM-driven discovery
era. Shay shares advice that companies should update their websites now to be
LLM-friendly by adding question-and-answer style content, refreshing pages, and
structuring information so models like ChatGPT, Claude, and Gemini can easily
understand and surface it. Kevin distinguishes between traditional SEO, which
can be influenced by what a company says about itself on its own site, and what
he calls generative engine optimization (GEO), which depends on consistent
corroboration across review platforms, communities, and industry media. This is
similar to “barnacle SEO,” where brands ensure they appear on all the key
properties that shape both search results and LLM outputs.
From there, the discussion turns to AI’s broader impact on go-to-market. Shay believes AI will sit at the center of the GTM engine, providing real-time insight into what prospects engage with and enabling faster optimization of campaigns. For BDRs and sales teams, that means better context and more relevant outreach; for demand gen leaders, it means quicker detection and repair of underperforming initiatives, but also more pressure to deliver. Both Kevin and Shay stress that AI augments, rather than replaces, human judgment: teams still need to interpret data, validate it through real customer conversations, and ensure that content remains authentic and trustworthy. Events, in-person interactions, and a clearly defined ideal customer profile (ICP) remain foundational to building the trust and relevance that AI alone cannot create.