Our Team

The operators behind your AI employees.

ShooflyAI is led by two Managing Partners, Jonathan Hessing and Diego Herrera Rios. We are operators and engineers who run our own company on the agents we build, then hand you the systems, code, and IP to keep.

Operators, Not Consultants We Run On What We Build You Own Everything
Managing Partners

Two operators. One standard.

ShooflyAI is run by people who use the same agentic systems we build for clients. We do not sell theory. We ship AI employees, then hand you the code, data, and models to keep.

Jonathan Hessing, Managing Partner at ShooflyAI
Managing Partner

Jonathan Hessing

Jonathan helps mid-market operators adopt custom AI employees, agents, and agentic operating systems that drive measurable ROI. He runs his own company on a fleet of AI agents he built, so the playbook he gives clients is one he uses every day. His focus is simple: hard ROI estimates before you build, and systems live in weeks, not quarters.

Leads AI strategy & operating systems

Diego Herrera Rios, Managing Partner at ShooflyAI
Managing Partner

Diego Herrera Rios

Diego leads the design and engineering of the custom AI agents and agentic systems clients own. A research professional turned AI architect, he builds infrastructure that companies can trust with core operations. His work centers on AI systems engineering, machine learning, and managed AI infrastructure built to run reliably at scale.

Leads AI engineering & infrastructure

How We Operate

We work the way good operators work.

Assessment first, ownership always, and outcomes you can measure on a P&L. These are the rules we hold ourselves to on every engagement.

You own it, you do not rent it

You own the code, data, models, and IP. On full payment, the work product is 100 percent yours. No vendor lock-in, no per-seat tax that grows forever.

Assessment before we build

We start with a paid diagnostic or operating assessment and give you a hard ROI estimate up front. If the numbers do not work, we tell you before you spend on a build.

Live in weeks, not quarters

We ship working AI employees into your operations in weeks. You see real output early instead of waiting two quarters for a slideware roadmap.

Measured on outcomes

We tie every system to a number you care about: deals closed, cycle time, cost saved. We win when that number moves, not when a project ships.

Proof You Can Defend

What that looks like on a real P&L.

One client, Strickland, ran the assessment, then we built the systems they now own. Real numbers, not promises.

22% → 41%close rate, nearly doubled
3 wks → 8 dayssales cycle, cut by two thirds
$15K → $28Kaverage deal size
We run our own company on the agents we build. The advice you get is field-tested on a live business, not pulled from a deck. We only win when the build is worth doing, so our incentive is your ROI from the first conversation.
Jonathan Hessing & Diego Herrera RiosManaging Partners, ShooflyAI
Questions We Hear

FAQ

Who runs ShooflyAI?

ShooflyAI is led by two Managing Partners, Jonathan Hessing and Diego Herrera Rios. Jonathan focuses on AI strategy and operating systems for mid-market businesses, and Diego leads the design and engineering of the custom AI agents and infrastructure clients own.

What makes the ShooflyAI team different?

We are operators and engineers, not consultants. We run our own company on a fleet of AI agents we built, and we give clients a hard ROI estimate before any build. You own the code, data, models, and IP we deliver.

Does ShooflyAI work with companies my size?

Yes. We build for mid-market operators running roughly $10M to $75M and up in revenue. We start with a paid assessment so the fit and ROI are clear before you commit to a build.

What results has the team delivered?

One client, Strickland, nearly doubled its close rate from 22% to 41%, cut its sales cycle from 3 weeks to 8 days, and grew average deal size from $15K to $28K, on systems they own outright.

How do I start working with the team?

Start with a paid $6,000 AI Operating Assessment. The fee credits 100 percent to your retainer if you move forward.

Do I own what the team builds?

Yes. On full payment you own 100 percent of the work product, including the code, data, models, and IP. These are AI employees you own, not software you rent.

Work With Us

Work with operators who own the outcome.

Start with a paid assessment and get a hard ROI estimate before you build. The fee credits 100 percent to your retainer if you move forward. AI Operations Retainers run on a 12-month term, scoped from your assessment.