Train your team.
Your AI tools are deployed. Half your team isn't using them.
Workforce AI fluency programs built on Win-Win Workplace research. Role-based training, written playbooks, champion networks, and workforce-outcome reporting that runs alongside your business KPIs.
Fixed fee · 2-12 weeks. Three tiers.
The pain you know
The tools are live. Adoption never landed.
You bought the AI tool. Three months in, half the team is still doing it the old way. The other half uses it for one thing. Roughly 60% of AI investments are wasted on adoption that never lands. Underneath the tool problem is a people problem: workers heard the announcement and started waiting to see if they'd be replaced. Adoption stalls because nobody wants to teach themselves the tool that might do their job.
What it does
Five focus areas your team learns to use AI in.
Upskill is a workforce fluency program. The curriculum covers the same five areas across every engagement, with depth that scales to your team's needs.
Working with AI without losing what you know
How to use AI as a multiplier for expertise, not a substitute for it.
Role-based workflows
The specific workflows your role handles, redesigned around what AI excels at and what it doesn't.
Prompting habits that actually work
The patterns that get reliable outputs from the AI tools you have in place.
Spotting the slop
AI sounds confident when it's wrong. Spot it, verify, and know when to push back.
Owning the change
What it means to be the AI expert on your team. Heaviest in Plus and Pro.
The foundation
The Win-Win Workplace foundation
“What if the most powerful growth strategy in business today isn't AI or cost-cutting, but your people?”
Upskill is built directly on the research Jackson published from her work across more than twelve hundred companies. Her finding: organizations that invest in workforce capability see profit margins up to 50% higher than peers and turnover nearly halved. The thesis is that companies don't grow by cutting people. They grow by making the people they have more valuable.
That research is the operating system underneath this product. Five principles run through every Upskill engagement, from Base through Pro.
Center employee voices
The discovery phase of Upskill includes interviews with the people who do the work, not just the executives who signed the check. The workshops we run, the playbooks we write, and the champions we name come from what the workforce actually told us.
Mutualistic working relationships
The deployments that stick are the ones where the worker gets something real (hours back, less drudgework, a job that grows) and the business gets something real (margin, throughput, retention). Both sides win, or neither does.
Develop deep talent benches
Most AI strategies say 'hire ten AI specialists.' That's the wrong move for a mid-market business. The right move is making the team you already have AI-fluent. They know the customers. They know the workflows. They know the institutional context that the new hire would spend a year learning.
Distributed leadership
The champion networks Upskill builds aren't a top-down assignment. They're the people inside each team who already get it, given the structure and the standing to coach their peers. Distributed leadership at the practitioner level, not just the org chart level.
Human capital reporting
Pro tier builds quarterly workforce-outcome reports for leadership, alongside business KPIs. The same way you measure CAC, MRR, or margin, you measure hours returned per role, fluency assessment scores, retention by team, and satisfaction with the AI deployment.
Generic AI training programs don't have this foundation. They sell you a course library and call it done. Upskill is engineered to make the workforce more valuable, because research shows that's where the margin actually comes from.
How it works
Four phases. Same as every Databender engagement.
The phases land slightly differently for Upskill because the deliverable is human capability rather than code. The Audit is the front door. Most Upskill engagements start there.
Audit
2 weeks
Senior diagnostic. We sit with leadership and the workforce, walk through where the AI tools are landing well and where they aren't, and come back with a ranked list of fluency gaps by role. The Audit report tells you which Upskill tier fits your situation, what the curriculum should cover, and which champions to name.
Implementation
2-12 weeks · Fixed fee by tier
The Upskill program itself. The executive briefing, the workshops, the playbooks, the champion bootcamp (Plus and Pro), and the Center of Excellence (Pro). On-site or remote, depending on team distribution. Most engagements run a mix.
Adopt
Embedded in Implementation · Included
The training, the playbooks, and the champion networks are put into practice and executed thoughtfully.
Run
Ongoing · Included in Pro, retainer-optional for Plus
Workforce-outcome reporting on a quarterly cadence (Pro). Office hours and escalation support from a forward-deployed Databender (Pro, ninety days). Optional ongoing coaching retainer for Plus engagements that want continued support past the 30/60/90 check-ins.
What you own when we're done
- Role-based adoption playbooks (one per role, written for your actual workflows)
- Executive briefing materials and the signed Workforce-First commitment document
- Champion network charter and training materials
- Change management framework with a 30/60/90-day plan (Plus and Pro)
- Center of Excellence charter, operating model, and intake process (Pro)
- Cross-functional fluency curriculum (Pro)
- Fluency assessment instruments and scoring rubrics
- Quarterly workforce-outcome reporting template wired to your business KPIs (Pro)
This is not a course library that turns off when the subscription lapses. If you run it again next year with a new team, you have everything you need to do it without us.
Workforce ROI tracked at Run
The metrics we track.
Hours returned per role
The single most concrete workforce metric. How many hours per week did the role get back from drudgework once the AI tool started getting used the way Upskill trained them to use it? Tracked by sampling and self-reporting. Baselined at the start and remeasured at thirty, sixty, and ninety days.
Fluency assessment scores
Pre- and post-measurements of how comfortable and capable each role is with the AI tools in their stack. Role-specific scenarios that mirror their actual work.
Satisfaction with the AI deployment
Survey instrument we run at baseline and thirty days post. How much does the worker trust the AI in their workflow? How much do they feel the deployment was done with them, not to them? The single best leading indicator of whether the rollout will stick.
Retention by team
Tracked over six to twelve months. The Jackson research shows that workforce-first companies see turnover nearly halved. Upskill engagements get added to that statistical base. We don't promise the same number for your company. We do measure it, and the data goes in the quarterly review.
Escalation patterns
What kinds of questions are workers escalating to champions? What are champions escalating to the CoE? What's the CoE escalating to Databender? Each layer of escalation tells us where the fluency is still thin, and the curriculum gets retuned accordingly.
These metrics aren't soft. They're the same shape as the business KPIs your CFO already trusts.
Pricing
Three tiers. Fixed price per tier.
Most mid-market clients land at Plus. Base fits companies that already have strong internal change-management muscle and just need the curriculum and playbooks. Pro fits companies that have publicly committed to a Workforce-First strategy and need a measurement structure to back it up.
Upskill Base
$12,500 · 2 weeks
Best for: Companies that already have strong internal change-management muscle and just need the curriculum and playbooks to round out an existing AI rollout.
Includes. Half-day executive briefing with a signed Workforce-First commitment, 3 role-based workshops scoped to the work each role actually does, 3 written adoption playbooks (one per role, with real prompts, workflows, and screenshots), and 2 to 3 champions identified and named by the end of the engagement.
Upskill Plus
Most common$25,000 · 4-5 weeks
Best for: The typical Upskill engagement. Most mid-market deployments land here.
Includes. Everything in Base, plus: 5 role-based workshops, 5 written playbooks, a champion network bootcamp that turns the named power users into in-house experts, a change management framework with a written 30/60/90-day plan and owners and milestones, and 30/60/90-day check-ins to review what's working, fix what isn't, and retune the playbooks.
Upskill Pro
$45,000 · 8-12 weeks
Best for: Companies that have publicly committed to a Workforce-First strategy and need a Center of Excellence and a measurement structure to back it up.
Includes. Everything in Plus, plus: 8 role-based workshops, 8 written playbooks, Center of Excellence setup (charter, operating model, governance, intake, escalation path), a 90-day coaching retainer with a forward-deployed Databender available to your CoE and champions, a cross-functional fluency curriculum so AI fluency travels across teams, and quarterly workforce-outcome reporting that goes to leadership alongside business KPIs.
Optional retainer (Plus and Pro). $2,500/mo for ongoing coaching, office hours, and quarterly reporting after the engagement closes.
Included in every tier. Discovery interviews with workforce and leadership, role-based curriculum scoped to your actual workflows, all written materials and playbooks, and the Workforce-First commitment document.
Common add-ons
Tight tiers are the headline. Add-on prices are transparent so you know the cost upfront, no negotiation.
| Add-on | Price |
|---|---|
| Workforce size beyond 200 staff | $5,000 |
| Custom curriculum for niche roles | $3,500 per role |
| On-site travel | Passthrough at cost |
| White-glove rollout (500+ workforce) | $20,000 |
| Custom assessment instrument development | $5,000 |
*Each tier price is fixed for the published tier scope. Final scope and price confirmed during the 2-week Data & AI Audit.
The Audit confirms which tier fits, the final scope, and the curriculum scoped to your roles.
FAQ
The questions leadership teams ask before booking the Audit.
Adoption is the deployment.
Imagine what your team can do when complemented by machines that work with them.