For high-capacity founders and growing teams who are tired of being the bottleneck, the translator, and the backstop for everything operational.
We redesign the human-heavy workflows that create the most drag — so your team moves faster, stays human, and AI quietly supports the process.
Answer 13 questions. Get your primary bottleneck identified. Know exactly where to start.
What clients actually walk away with
Most founders start at Level 1 and walk up the ladder. You don't have to commit to the biggest thing first — you just have to take the next right step.
$97 / month
A low-risk way to experience our thinking, the community, and the methodology before you commit to anything bigger.
$1,500–$2,500
A time-bounded look at your specific business that produces a concrete roadmap — and shows you exactly where the Sprint will move the needle first.
Starting at $5,000
Our one flagship implementation offer — the most complete, most transformational way we work with founders. We install AI-supported workflows your team can actually run without you in the room.
Custom · Starting at $8,000/mo
Jennifer joins your leadership team as your Chief AI Officer. She owns the AI function, builds the systems, trains your people, and stays until the job is done. For founders ready to integrate AI at the leadership level.
The Sprint is the right starting place for most founders. Need something more specialized? A focused AI Agent Build tackles one specific workflow, and the Fractional Chief AI Officer is for founders ready to integrate AI at the leadership level across the whole business.
No more white-knuckling the business you built to be free.
We spent 13 years inside the operational engine of high-volume sales organizations — running systems, building lead funnels, and coaching 5,000+ professionals through the same chaos you're sitting in right now. Along the way, we built over 10,000 workflows that powered the ads behind those funnels. We know what it feels like to be the person every decision routes through.
Jennifer Bennett and her mom, Darlene Greer — a second-generation entrepreneur — founded Get Desky for one reason: to build operational frameworks where excellence never has to cost you your presence. We step in to give high-capacity founders their strategic white space back. Not more dashboards. Not more tools. The actual mental and calendar space to lead like a CEO again.
We also own and manage one of the largest local Facebook communities in our city, growing it to over 30,000 members — so we know what it takes to build something real with humans at the center. That same philosophy drives every system we architect: human-driven, AI-leveraged, brutally simple.
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From operational systems that scale to human-driven AI workflows and the leadership shifts behind sustainable growth, we bring honest, actionable frameworks to stages of all sizes. Audiences walk out with systems they can build — not slogans they'll forget by Monday.
"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."
No more operational drag. No more letting outdated systems constrain your growth. No more burning out with operational chaos. Let us engineer the architecture that actually scales.