— Pillar III · Programs —

Past the one-off project. Built for the long arc.

Three tracks for businesses that need ongoing technical leadership, packaged outcomes, or structured learning. Pick the shape that fits where you are.

Book a fit call→Compare tracks

— Three tracks —

i.

Retainer

Ongoing care

Monthly engagement with rolling hours and availability. For businesses with an active stack that needs continuous attention but doesn't justify a full-time hire. Three tiers from Operator to Fractional CTO.

ii.

Bundle

Packaged outcome

Fixed-scope multi-service engagement tied to a specific business outcome — a launch, a migration, an automation rollout. Single price, defined deliverables, clear start and end. Three named bundles to date.

iii.

Cohort

Structured learning

Time-bounded group engagement for business operators who want to build technical fluency on AI and automation, not be sold a solution. Hands-on, small-group, with a working deployment at the end.

— Track i · Retainer —

Continuous care for an active stack.

Three tiers ranging from regular operational care to embedded fractional-CTO. Pick by hour budget and response SLA. All tiers include same-day response on urgent issues and a quarterly architecture review.

Operator

$2,000/mo

Ongoing care for an existing deployment.

  • 10 hours of work per month, rolling
  • Same-day response on urgent issues
  • Quarterly architecture review
  • Includes Pitt Sentinel monitoring on your stack
  • Cancel anytime, no minimum commitment
Discuss retainer
Recommended

Partner

$5,000/mo

Embedded operator role on a single business.

  • 30 hours per month, rolling
  • Direct Slack / Discord channel; 4-business-hour response
  • Monthly priorities sync
  • Quarterly architecture review + roadmap update
  • First option on new AI / automation work
  • Three-month minimum
Discuss retainer

Fractional CTO

$8,500/mo

Strategic and hands-on, for businesses without an in-house technical leader.

  • 60 hours per month, rolling
  • Direct stakeholder access; same-business-day response
  • Vendor selection, hiring input, and technical due diligence
  • Quarterly board-level reporting
  • Six-month minimum
Discuss retainer

— Track ii · Bundle —

Packaged for an outcome.

Three named bundles built around shapes we see often. Single price, defined deliverables, clear start and end. If your shape isn't one of these, see Custom Business Solutions.

  1. i.

    from $4,500

    Launch Program

    For brand-new businesses. LLC formation, website, custom domain + email, and an inbound-intake AI workflow — wired together as one engagement.

    • Business Formation (Standard)
    • Web Builds (Starter)
    • AI Integration (intake workflow)
    • Domain + email setup

  2. ii.

    from $7,500

    Operations Program

    For existing businesses with manual workflows eating staff hours. Self-hosted automation runtime + 5 custom workflows + first AI integration + 90 days of optimization.

    • Workflow Automation (Pro)
    • AI Integration (one workflow)
    • Pitt Sentinel monitoring
    • 90-day optimization included

  3. iii.

    from $12,500

    Sovereignty Program

    For businesses moving off SaaS. Self-hosted cloud + private file sync + Zero Trust access + email/calendar migration + 6-month operator retainer.

    • Pitt Cloud (Family)
    • Zero Trust Setup
    • Migration and training
    • 6 months of Operator retainer

— Track iii · Cohort —

Learn to use AI. Not be sold AI.

Six-week, small-group cohorts for business operators. Hands-on, real workflows, working deployment at the end. Maximum eight operators per cohort.

i.

6 weeks, monthly cohorts

$1,800 / seat

AI Foundations for Operators

For business owners who want to actually use AI rather than be sold AI. Six sessions covering: model choice, prompt patterns, RAG over your docs, integration into existing tools, cost monitoring, and the failure modes nobody warns you about.

  • Group sessions (5–8 operators per cohort)
  • Hands-on labs against your real workflows
  • One private 1:1 mid-cohort
  • Completed RAG-over-your-docs deployment at the end
Join the waitlist→

More cohort topics planned. Tell us what you'd learn in.

— Common questions —

Answered before you ask.

— Next step —

Not sure which track?

Book a 30-minute fit call. We'll walk through where you are, what you need most, and which track — if any — would actually move the needle. Honest answer either way.

Book fit call→Email us instead