AI Advisory for business

Find your path forward.

I help businesses improve the customer experience through smarter systems and automation.

Est. 2026 — Detroit, MI

I bring over 20 years of real operating experience to the table. I've run the business, owned the numbers, and answered for results.

Cairn is built by operators, for operators.

About Me
Jacob Fenton
Jacob Fenton, Founder & CEO

I've built my career inside some of the most demanding digital businesses in the world.

I bring 20+ years of experience leading marketing, customer experience, and product functions for global brands. I specialize in helping companies solve problems by building the systems and processes that increase loyalty, trust, and lifetime value.

My leadership spans startup through global scale, from Amazon's early connected-device ecosystem to StockX's worldwide dual-sided platform.

Certifications
Education
MBA
BBA
CX Certificate
VP, CX & Product Marketing

Built the global CX program from scratch. Managed 1B+ CRM messages annually, drove brand trust from 27% to 48%, and applied AI to unstructured customer data.

Marketplace Detroit
VP, Business Operations

Ran Business Operations across CrowdRise through its acquisition by GoFundMe — managing large cross-functional teams, building KPIs, and driving a streamlined customer service experience.

Platform Detroit / SF
Senior Product Manager

Led Kindle and pioneered the Dash Replenishment Service — a recurring-revenue channel built across four major OEMs, with strategy presented directly to Amazon's CEO.

Product Management Seattle
Industries

Where I focus...

01
Concierge Medicine

Independent and boutique practices using AI to elevate the patient relationship and reduce operational friction.

Case study 44 handouts, four tools, one solo practice. Read the build →
02
E-Commerce & Retail

Marketplaces, DTC brands, and omnichannel retailers navigating AI-driven personalization, CRM, and operations.

03
Consumer Tech

Apps, platforms, and software companies integrating AI into product experience and the customer journey.

04
Small Business Entrepreneurs

Real estate operators, promotional products, CPAs, coaches, and service businesses using AI to compete and operate more efficiently.

How I Help

Work we do
together.

Every engagement starts with the same question — where does your business actually stand today — and proceeds in steady, useful steps from there. No big-bang transformations. No tools bought before the work is understood.

01
The AI Audit

A clear-eyed look at where your business actually stands — before a single tool gets purchased. We identify the highest-leverage opportunities and produce decisions, not a slide deck of possibilities.

Learn More →
02
Implementation & Integration

We work inside your operations to build AI into the systems your team already uses. No big-bang transformations — steady progress that sticks because we built it with your people.

03
Ongoing Advisory

AI moves fast. Your business does too. I stay alongside you as a trusted resource — helping navigate new tools, prevent expensive mistakes, and build internal capabilities.

Trail Notes

Notes from the trail.

All Notes →
Case study May 2026 — 6 min read
44 handouts, four tools, one solo practice.

What AI advisory work actually looks like when it's pointed at the real work of running a small business — and the compounding return that shows up after the first week.

Read the note
Field note April 2026 — 7 min read
What it actually means to run an AI assessment.

"AI Assessment" is becoming one of those phrases that sounds important but often means very little. A real one identifies where AI can create measurable impact — and where it shouldn't be used at all.

Read the note
Field note April 2026 — 6 min read
How to tell if someone actually knows what they're doing in AI.

There's a lot of confidence in the AI market right now. There's not nearly as much competence. Here's how to tell the difference before you spend.

Read the note
Get in Touch

Find
your footing.

It's never been a better time to build. Let's talk.