Derek Phillips
Fractional Digital Strategy Lead
Grounded in 20 years of enterprise rigor.
Fractional Digital Strategy Lead
Grounded in 20 years of enterprise rigor.
In a world of generative AI content and automated workflows, the most expensive mistake is assuming a tool can replace a strategy.
AI can generate text, but it cannot navigate the complex internal politics of a global relaunch or identify the quiet, predictable failures that kill your technology ROI.
There are some things you simply cannot automate:
Contextual Governance: AI doesn't know who is actually accountable for your content or how to build the "M" in your CMS so it doesn't become a "sophisticated junk drawer."
Stakeholder Alignment: Tools don't lead discovery workshops or conduct the stakeholder interviews necessary to turn ambiguous business needs into a clear vision.
Human Sentiment: I specialize in extracting the "human moment" from raw data; shaping narratives that make a user stop scrolling because they feel seen, not just targeted.
I have a lot of thoughts on this and you can read them (and more!) on The Signal Path, my blog and confessional.
I am Derek, Your Digital Strategist. If I had to describe myself in five words, I would say, "More clever than smart. Funny." I have spent two decades working with big agencies and brands, and I have learned that playing the smartest person in the room is a rigid trap.
I focus on the "Day Two" of digital transformation; the moment after go-live when the real work of governance, optimization, and scaling begins.
1. The Architect: Digital Experience Roadmaps
I don't rely on intuition or templates. I draw on 20 years of patterns learned from the world’s biggest brands to build multi-year roadmaps grounded in consumer research and competitive audits.
2. The Operator: Content Systems & Governance
Content isn't a volume game; it's an asset management challenge. I build the operating models, editorial workflows, and quality standards that allow your team to scale without the chaos.
3. The Strategist: Connecting Brand to Commerce
I ensure your brand promise and your commercial outcomes are the same priority. From acquisition to retention, I connect your channel strategy to measurable human behavior.
I bring the clever strategic direction, you bring your internal expertise, and together we find some great insights. Check out my services and let's see if there's something I can do for you.
I bring the rigor of an enterprise executive to the agility of a mid-market partner.
Scaled a 35-person practice at Concentrix Catalyst, driving 198% revenue growth through two acquisitions.
Standardized global operations for Critical Mass, ensuring strategic consistency across international offices for brands like AT&T, SUPERVALU, Valvoline and Nissan.
Led 1,600+ asset audits and large-scale CMS migrations for AARP and the National PTA, fixing the structural debt that kills digital performance.
I've worked with some awesome people and I have been lucky enough that many have said nice things about me. Check out my references and see for yourself.