I help businesses establish the leadership, standards, systems, and habits required to use AI well. Before unmanaged adoption makes them slower, riskier, and less competitive.
As your Fractional Chief AI Officer, I help turn scattered experimentation into clear priorities, practical guardrails, useful systems, and team practices that hold up in real work. People keep the judgment, relationships, and accountability.
A paid, facilitated assessment of current use, readiness, and priorities.
Explore Fractional AI Leadership →Need someone to lead the function? You can begin there.
What I help you establish
One person is drafting with AI. Someone else is testing an automation. A new subscription appears, and a few useful experiments begin to spread.
The team is moving. The business may still be missing the decisions that connect the work.
Which opportunities deserve time and investment?
What information, outputs, and actions are acceptable?
Who checks the work and owns what happens next?
How does the team learn a reliable way to use it?
Those are leadership decisions. I help you make them and carry them into the business.
An AI agenda connected to business goals, with clear priorities and decision ownership.
Practical boundaries for approved use, information handling, quality, and human review.
AI-supported workflows that fit the business, with understandable handoffs and documentation.
Training, practice, feedback, and review that help the team use AI responsibly over time.
The point is not to make the business look more advanced. It is to build a capability the business can lead, use, and improve.
I establish the standards and decision rights around how AI is used.
I help choose what is worth building, what needs preparation, and what should wait.
I turn approved priorities into workflows, systems, and working practices.
I help the team practice, review, and improve until responsible use becomes part of the work.
I stay connected to implementation because a decision is only useful if people can act on it. I stay connected to the people because adoption is more than a launch.
$97 / month
A low-risk way to experience our thinking, the community, and the methodology before you commit to anything bigger.
Custom · Starting at $8,000/mo
I lead the AI function within an agreed mandate, from priorities and standards through implementation and team adoption.
$1,500–$2,500
I establish what is happening now, what needs attention, and what belongs in the first 90 days.
Starting at $5,000
I help install the initial AI Operating Foundation across selected workflows and team practices.
$750 per person · Custom builds from $2,500
I guide a controlled implementation experiment around one appropriately scoped use case.
I help build a defined AI capability inside the workflow, standards, and review process it needs.
These are different scopes of support, not purchases you have to complete in order. If the business needs an AI leader, we can start with that conversation.
Depending on the engagement, the work can include an approved AI-use standard, a prioritized use-case roadmap, a human-review process for client-facing outputs, or a workflow with named ownership and quality checks. Team practice and leadership review connect those pieces to what happens after launch.
I want you to be able to see what changed, who owns it, and how it is helping. A working capability should leave more evidence than a collection of tools.
AI should strengthen your business. Not leave your people guessing.
I help leaders and teams responsibly integrate technology so it actually works inside the business. I care about the decisions, the systems, and what those systems ask of the people using them.
I co-founded Get Desky with my mom, Darlene Greer, on Christmas Day 2020. As a third-generation woman entrepreneur, wife, and homeschool mom, I want a business to create capacity and opportunity without consuming the people building it.
Get to Know Me
I speak with founders, leaders, and teams about the responsibility behind AI adoption. I help the room move from scattered possibilities to clearer decisions about what to lead, protect, build, and practice.
"Jennifer addressed something our community feels deeply — the tension between scaling a business and staying human in the process. She walked attendees through systems and simple processes for follow-up and relationship management using AI, without sacrificing the personal touch."
"She brought clarity, intentionality, and a relationship-first approach to the stage, teaching our attendees how to use AI to find the right people, build real relationships, and follow up without sounding robotic."
"Joining the Work Smarter Inner Circle was one of the best decisions I have made. Jennifer Bennett has brought together the most amazing group of entrepreneurs intent on growing and building their businesses in smart and efficient ways."
"As a busy social media professional, joining the Work Smarter Inner Circle has been a game-changer for my business. The connections I've made have led to valuable collaborations and even client referrals. Since joining, I've implemented strategies that allowed me to confidently raise my rates."
"You need someone who is willing to look at what you're doing and tell you what's not working. You need to be surrounded by people who will love you enough to tell you the truth and also help you fix what's broken. Jennifer has a knack for gathering them together."
"I love the Work Smarter Inner Circle. One of the most valuable things, thus far, is the relationships that I am building. I am finding that the people who are in this group are top-tier quality people."
"It's technically been one month. I wish I would've listened to you both sooner. You, Jen Bennett, and you, Darlene Greer, have changed my life."
"As someone with ADHD managing multiple businesses, it's been a lifesaver. They're not just efficient — they're also incredibly personal and understanding."
If AI is entering the work, the next step is to decide how the business will lead it. I can help you establish the priorities, guardrails, systems, and team practices that make that possible.