Technology Recommendations & Execution Plan
Four categories of recommendations spanning immediate pre-event fixes, organizational restructuring, growth strategy, and architecture modernization.
Four Categories of Recommendations
After reviewing the current systems, codebase, analytics, and team structure — and meeting with both the executive team and the engineering team — I'm presenting four categories of recommendations:
- Immediate fixes before March UPW — cart validation, portal access, reporting
- Organizational restructuring — Build vs. Run teams
- Growth strategy — from event-dependent to recurring revenue
- Architecture modernization — Q2-Q4 roadmap
The good news: The engineering team has already made significant improvements that haven't been fully communicated to leadership.
The bad news: The organizational structure guarantees recurring crises. Fixing the structure is more important than fixing any single system.
What's Already Fixed (That You May Not Know)
Before recommending changes, it's important to acknowledge work already completed by the engineering team:
| Issue | Previous State | Current State | Status |
|---|---|---|---|
| Page load speed | 19+ seconds (GTM scripts blocking render) | Scripts deferred to window load | Fixed |
| Portal access delay | 4-6 hours | 3-5 minutes (logic moved out of Salesforce) | Fixed |
| Apple Pay | Disabled due to bug | Re-enabled on Stripe | Fixed |
| Google Pay | Working | Working | No change needed |
| European checkout | Apple Pay disabled; iframe cross-origin issues | Apple Pay re-enabled; checkout functional from all locations | Fixed |
| Salesforce bottleneck | All business rules ran inside Salesforce | Fulfillment objects inserted directly | Fixed |
| Data lake | No centralized data | AWS Glue → S3 → Redshift lake house | Completing this week |
Key insight: The engineering team shipped meaningful improvements in December–January. The communication gap between engineering and leadership is itself a problem to solve.
Immediate Fixes Before March 12
2A. Checkout — Validate, Load Test, and Harden
Current state: The checkout is functional. Apple Pay is re-enabled, European customers can purchase, and the GTM bottleneck is resolved. The immediate fires are out.
Remaining risk: The checkout uses a multi-layered iframe architecture that is inherently fragile. When a customer clicks "Order Now," it loads an iframe from tonyrobbins.com/widget/order-form, which then loads 5+ additional Stripe iframes inside it (address fields, payment fields, Google Pay, hCaptcha, Google Maps autocomplete). That's up to 4 levels of iframe nesting across 6+ domains. We verified it works today — but it broke repeatedly under load during the summit. The architecture is vulnerable to browser security updates, ad blocker changes, third-party cookie deprecation, and cross-origin policy shifts.
What we need before March:
- Comprehensive load testing from real browsers worldwide — not server-side stress tests. Actual browser-based synthetic testing:
- 30,000+ concurrent sessions from US, UK, Germany, Australia, Brazil
- Chrome, Safari, Firefox, Brave, iOS Safari, Android Chrome
- With common ad blockers and privacy extensions enabled
- Measuring page load, checkout render time, and payment completion
- Pre-event checkout validation checklist: Apple Pay e2e, Google Pay e2e, credit card from US/UK/EU, mobile browsers, desktop with ad blockers, quantity > 1, promo codes, error states
- Continuous synthetic monitoring: Automated checks every 5 minutes against live checkout. Alert Run team if load exceeds 3 seconds or checkout fails.
Recommended tools: Checkly or Catchpoint for synthetic monitoring. k6 with browser module or BrowserStack for real-device load simulation. These become permanent infrastructure.
Longer-term (Q2): Replace the iframe-based checkout with Stripe Payment Element — a direct integration not locked to a domain whitelist, removing the 4-layer iframe nesting entirely.
2B. Portal Access — From 3 Minutes to 20 Seconds
Problem: Customers wait 3-5 minutes (previously hours) for confirmation email and portal access. During a live event selling the next event, even 3 minutes feels broken.
Root cause:
- Order enters Heroku job queue (~1.5 jobs/second at peak)
- Email triggered through HubSpot's API
- HubSpot rate limit: 200 calls per 10 seconds
- At summit scale, HubSpot becomes the bottleneck
Solution: Send the confirmation email directly from the order processing API (SendGrid, Postmark, or AWS SES) and log the email-sent event back to HubSpot as an activity on the contact record. Customer gets email in ~20 seconds. Marketing still sees the event in HubSpot. No data is lost.
Prerequisite: IP warm-up for the new sending domain. 30 days is sufficient — this needs to start immediately.
2C. Landing Page — Dual-Deploy Strategy
Problem: Marketing builds pages in HubSpot for flexibility. But HubSpot pages are slow — heavy CMS overhead, third-party scripts, no edge caching.
What we already proved: I rebuilt the UPW landing page as a static page deployed to Cloudflare Pages — sub-second load, served from 300+ edge locations worldwide, identical design.
Proposed workflow:
- Marketing continues building pages in HubSpot (no disruption)
- Before major events, "snapshot" the final page and deploy to Cloudflare Pages
- DNS points traffic to Cloudflare during high-traffic events
- After event, revert to HubSpot for ongoing edits
Marketing keeps their tools. Customers get a fast page. Engineering gets peace of mind.
2D. Salesforce Reporting — Use What You Already Have
Problem: Leadership can't see real-time sales data during events. Salesforce reports are 3-4 hours behind.
Solution: Build 2-3 QuickSight dashboards against the operational database (live Heroku Postgres) for real-time event reporting. Key dashboards: live sales by SKU/time, conversion funnel, revenue by geography.
Organizational Restructuring — Build vs. Run
This is the most important recommendation in this document.
The Core Problem
The current team structure combines everyone into one group that does everything: operations, maintenance, new development, event support, DevOps, QA, and firefighting. The result:
- Developers get pulled to events to set up kiosks
- The same people running production are building new features
- No sprint has been closed in 3 weeks
- The team worked 3-4 weeks straight of 10-hour days and burned out
- Half the team is currently sick or on vacation
- When fires happen, all development stops
- When development is prioritized, operational issues pile up
This is not a people problem. This is a structure problem. The current structure guarantees failure regardless of who fills the roles.
Current Structure
Proposed Structure: Build Team + Run Team
How It Works in Practice
| Aspect | Run Team | Build Team |
|---|---|---|
| Methodology | Kanban (continuous flow) | 2-week sprints with planning |
| Work type | Incidents, maintenance, monitoring, event ops | New features, migrations, improvements |
| Prioritization | Severity-based (P1/P2/P3) | Quarterly roadmap + sprint planning |
| Budget | Operational (predictable monthly) | Project-based (phased funding) |
| Staffing | Stable, no reassignment during events | Protected from operational interrupts |
| Emergent work | 100% reactive — this IS their job | 80% planned, 20% buffer for urgent |
Key Principles
- Run team never builds new features. They fix, maintain, monitor, and support.
- Build team never gets pulled for event ops. They plan, build, test, and ship.
- Event operations use contractors, not developers. Kiosks are not engineering work.
- QA is consolidated — one supports Run, one supports Build.
- Spork leads the Run team and stays as architecture authority across both teams.
- Justin leads the Build team and stays as product authority — roadmap, priorities, UX decisions.
Budget Impact
| Role | Purpose | Est. Annual Cost |
|---|---|---|
| AI Engineering Workshop | Cole Medin — upskill all engineers on AI-native development | $20K (one-time) |
| Systems/DevOps Engineer | Infrastructure, Heroku migration, monitoring | $130-150K * |
| Integration Engineer | Salesforce, data pipelines, API maintenance | $120-140K * |
| Data Engineer | Lake house, dashboards, analytics | $130-150K * |
| Event Ops Contractors (2) | Kiosk setup, event tech support | $50-80K/yr |
Total additional investment: $450-520K/year + $20K one-time workshop
* Roles marked with * are subject to review after the AI Engineering Workshop. Once the team is upskilled and AI agents are deployed to support workflows, some positions may be reduced in scope, delayed, or eliminated entirely.
What this buys: protected Build team that ships on schedule, dedicated Run team that handles incidents without stopping development, no more burnout, real sprint velocity, and predictable delivery timelines.
What it saves: lost revenue from broken checkouts (millions per event), support costs, delayed project opportunity cost, and employee turnover from burnout (replacing a senior engineer costs 1.5-2x salary).
3D. AI Engineering Upskill — The $20K Force Multiplier
Before hiring anyone, invest in the team you already have. A 2-day intensive AI Engineering Flow workshop led by Cole Medin — one of the leading practitioners in AI-native development — will bring every engineer up to a new standard of building with AI.
What this covers:
- AI-assisted development workflows — how to write, test, and ship 3-5x faster using AI coding tools
- Building AI agents — how to create autonomous agents that handle repetitive engineering and operational tasks
- Prompt engineering for production systems — not chatbots, but real AI integrated into business workflows
- Evaluating build vs. buy — when to build custom agents vs. use existing tools
The goal isn't to replace engineers — it's to turn each one into a team of five. A $20K investment that potentially saves $300K+ in hiring.
3E. AI Agents — Augmenting the Team Before Expanding It
After the workshop, the next step is an AI agent audit of the current roadmap and operational workflows. Before filling any open headcount, we inspect every planned hire and ask: can an AI agent handle 80% of this role?
The process:
- Map current workflows — document what each team does daily, weekly, monthly
- Identify agent opportunities — repetitive tasks, data processing, monitoring, reporting, triage
- Build and deploy agents — starting with highest-impact, lowest-risk automations
- Evaluate remaining gaps — only hire for what agents genuinely can't do
Likely agent candidates:
- Monitoring Agent — watches production systems, triages alerts, escalates only real issues (reduces DevOps load)
- Integration Agent — handles Salesforce sync, data pipeline failures, retry logic (reduces integration engineering load)
- QA Agent — automated regression testing, visual diff checks, pre-deploy validation
- Reporting Agent — generates daily/weekly dashboards, pulls data from lake, formats for leadership
- Support Agent — handles L1 internal support tickets, routes to right person, maintains knowledge base
The principle: Hire humans for judgment, creativity, and relationships. Deploy agents for everything repeatable. Every agent you build is an employee you never need to hire, manage, or replace.
Growth Strategy — From Event-Dependent to Recurring Revenue
The Structural Problem
The business model is almost entirely event-dependent and transactional. Revenue depends on filling arenas and virtual rooms, event by event, campaign by campaign.
| Tier | Product | Price | Model |
|---|---|---|---|
| Free | Summit | $0 | Lead gen (1.2M registrants) |
| Entry | UPW Virtual | $495 | One-time ticket |
| Mid | Life/Wealth Mastery, Leadership | Varies | One-time virtual tickets |
| Premium | Business Mastery, Date with Destiny | $2K-10K | One-time in-person |
| Ultra-Premium | Life & Wealth Mastery Fiji | $10K+ | One-time in-person |
| Subscription | Inner Circle | $97/mo | Content + group coaching |
| Subscription | Tony Robbins AI | $99/mo ($390/yr) | AI voice coaching |
| Subscription | Business Accelerator | $995/yr | Membership + masterclasses |
| Coaching | Results Coaching | $695/mo | 1-on-1 with trained coach |
| Elite | Platinum Partnership | $85-120K/yr | Travel, elite access |
When the checkout breaks at the summit, revenue falls off a cliff — because there's no recurring base to cushion it. The 10% YoY decline isn't just a marketing problem. It's a model problem.
The existing subscriptions (Inner Circle $97, Tony AI $99, Business Accelerator $83/mo) are low-priced, loosely connected to the event experience, and not positioned as the natural next step. They feel like add-ons, not a path.
The goal: Make every event attendee a subscriber, so that between events, revenue continues, engagement deepens, and the next event sell becomes a renewal — not a cold reacquisition.
4A. The "Mastery Path" — A Unified Progression System
The gap: Someone attends UPW, gets fired up, goes home, and... nothing structured happens. There's no guided bridge between the $495 event high and ongoing transformation.
The concept: A single, structured progression system that every customer enters at their first event.
- Level 1: Foundation — Post-event implementation program + Tony AI + community. Included 90 days post-event, then $149/mo.
- Level 2: Growth — Advanced content, peer accountability groups, monthly group coaching. $249/mo.
- Level 3: Mastery — Bridge to Results Coaching or Business Accelerator. $497/mo.
- Level 4: Leadership — Teach, lead communities, become certified. Application-based.
Revenue impact: If 20% of UPW attendees (3,000 of 15,000) enter at $149/mo, that's $5.4M in annual recurring revenue from a single event cohort. It compounds with every subsequent event.
4B. Post-Event Implementation Program — The Missing Bridge
The biggest drop-off happens in the 30 days after an event. The emotional peak fades, patterns return, people drift.
The product: A structured 90-day program starting the day the event ends. Not content. Not a replay. A daily practice system.
- Week 1-2: Integration — daily 10-minute exercises. Tony AI guides with personalized prompts.
- Week 3-8: Practice — weekly challenges, peer accountability pods (5-7 people), live group coaching every 2 weeks.
- Week 9-12: Momentum — 12-month goals, daily rituals, "transformation story" presentation. Celebration event.
Pricing: Bundled into Mastery Path ($149/mo) or standalone $397 one-time.
4C. Tony AI as Connective Tissue — Not a Standalone Product
Currently Tony AI competes with Inner Circle ($97/mo) and Business Accelerator ($83/mo) for the same wallet. Three low-cost subscriptions that feel similar from outside.
Reposition: Tony AI becomes the platform layer connecting everything:
- After UPW: Implementation coach with personalized daily prompts
- Before next event: Reviews what you learned, sets intentions, identifies breakthrough areas
- During coaching: Reinforces sessions between calls, tracks commitments
- In the portal: Intelligent layer on all content — recommends based on history and progress
- For sales: Qualifies leads via conversation before a human calls
Tony AI stops being a $99/mo product and becomes included in every Mastery Path tier. Its data becomes the most valuable asset in the business.
4D. Annual Event Passport — Predictable Revenue
Every virtual event is sold individually, requiring a full acquisition campaign each time.
- Event Passport — All virtual events for one year: $1,997/yr
- Event Passport + Mastery Path — All events + progression: $2,997/yr
- Event Passport VIP — All virtual + one in-person event: $7,997/yr
Revenue impact: 5,000 passports at $1,997 = $10M in predictable annual revenue — locked in before a single event campaign runs.
4E. Load Testing as Revenue Protection
The summit cost millions because no one knew it was broken until customers reported it. Implement permanent synthetic monitoring and load testing: 30K+ concurrent sessions from 12+ countries, real browsers, real devices. Pre-event confidence reports to leadership.
4F. Speed-to-Lead: 8 Minutes → 60 Seconds
Lead routing flows through HubSpot → Salesforce → LeanData → sales rep. 7-8 minute delay. Responding in 1 minute vs. 5 increases conversion 3-5x.
Fix: Bypass Salesforce for routing. Webhook from HubSpot to a lightweight service that notifies the rep via SMS/Slack in 30 seconds. Better yet: Tony AI as first responder — qualifies the lead and warms them before the call.
4G. Activate the 700K Summit Leads + 4.5M Dormant Database
700K new leads (now): "Bring a friend" referral, SMS sequences, Meta/Google retargeting, physical mail to 33K cart abandoners.
4.5M dormant (Q2): Segment by value (phone call vs. email vs. direct mail), use the data lake, run a reactivation micro-event, build lookalike audiences.
4H. European Market + Local Payment Methods
Enable Klarna (installments), SEPA Direct Debit, iDEAL, Bancontact in Stripe. 1-2 days of configuration. Target EU summit attendees who couldn't checkout before.
4I. Real-Time Event Intelligence
Real-time dashboards during events enable mid-event offer adjustments, flash promotions to segments, and data-driven decisions instead of panic. Half of the panic comes from not knowing.
4J. Corporate/B2B Channel
No product exists for teams. A B2B subscription: team Tony AI access, quarterly workshops, custom Mastery Path tracks, engagement dashboards. $500-2,000/seat/year. One 50-person company = $50K replacing 100 individual subscriptions.
Architecture Roadmap — Q2-Q4 2026
The Tony Robbins OS — The Brain of the Business
Every system RRI runs today — Salesforce, HubSpot, Heroku, the portal, coaching tools, event platforms — is a disconnected island. Data lives in silos. Teams context-switch between 10+ tools. No single view of a customer exists.
The vision: Build a Tony Robbins Operating System (TROS) — a centralized intelligence layer that connects every system, powers every team, and gives every employee a custom work interface built for their role.
Backstage — Role-Based Dashboards:
- Executive Dashboard — real-time revenue, event sales, MRR/ARR, coaching pipeline, agent activity, escalations
- Events Dashboard — logistics checklists, attendee management, real-time sales during events, satisfaction tracking
- Sales Dashboard — lead pipeline, speed-to-lead metrics, conversion rates, Tony AI qualification handoffs
- Marketing Dashboard — campaign performance, audience segments, page speed, funnel analytics
- Coaching Dashboard — member progress, session notes, health scores, renewal predictions
- Operations Dashboard — system health, integration status, ticket queue, SLA tracking
Frontstage — Customer-Facing Intelligence:
- Tony AI Concierge — the unified customer touchpoint across web, app, SMS. "What program is right for me?" / "What's my Mastery Path progress?" / "Connect me with someone in my cohort"
- Unified Portal — single sign-on across all products. Progress tracking, event history, content recommendations powered by the shared brain
The Shared Brain — a single data layer powering everything:
- Customer profiles (enriched continuously from every touchpoint)
- Event history and transformation metrics
- Coaching program content and progress
- Sales and marketing intelligence
- Operational knowledge base (playbooks, runbooks, escalation procedures)
How we get there — The AI Org Chart Framework:
Following the transformation methodology from The AI Org Chart, we execute in three phases:
Phase 1: Map — Document the current org chart, every role's workflows, tools, and data touchpoints. Identify where humans are doing work that machines should own.
Phase 2: Vision — Create the AI Org Chart — a parallel digital org chart where every department has AI agents handling the repeatable, the predictable, and the data-heavy. Humans focus on judgment, relationships, and creative strategy.
Phase 3: Build (AAA Framework)
→ Automation (The Hands) — Basic task automation. Data syncs, report generation, alert routing, email triggers. Quick wins, immediate ROI.
→ Augmentation (The Suit) — AI-assisted workflows. Tony AI as coaching assistant, sales lead qualifier, event intelligence layer. Humans in the loop, AI doing the heavy lifting.
→ Autonomy (The Brain) — Self-operating systems. Agents that monitor, decide, and act without human intervention. The OS runs the business while leadership steers it.
Prerequisites — Planning Period:
- Executive requirements sessions — 2-3 workshops with leadership to define what each department needs from the OS
- Justin leads product roadmap — translates requirements into a phased build plan with the Build team
- Data architecture review — ensure the data lake can serve as the shared brain
- Agent inventory — map which AI agents are needed per department (output of the AI Engineering Workshop)
Q2 2026 (April-June)
1. Heroku Migration — Contract ends September. Move order ingestion API and job queue to own virtualization (Sacramento/San Diego). Already planned.
2. Checkout V3 — Replace custom Stripe cart entirely. Stripe Payment Element with native Apple/Google Pay. Works from any CMS. Mobile-first, i18n for Europe.
3. Real-Time Data Pipeline — Increase lake sync to near-real-time. Build executive dashboards in QuickSight.
Q3 2026 (July-September)
4. Portal Unification — Merge 11 customer portals into single Tony Robbins Experience. New SSO. Built on Sanity + Next.js.
5. Salesforce Rationalization — Move reporting to data lake/QuickSight. Salesforce becomes CRM + finance only. Evaluate Blackthorn replacement with batch optimization (200-record bulk loads).
Q4 2026 (October-December)
6. Marketing Independence — Evaluate dedicated page builder (Webflow, Unbounce, or enhanced Sanity). Amplitude integrated across all touchpoints. Audience building and export.
7. CRM & Sales Engagement Review — Evaluate Salesloft/Outreach to replace Salesforce Sales Engagement. Target: lead response under 60 seconds.
Process & Planning Discipline
Quarterly Technology Planning
- What we accomplished — demo, not slides
- What's on the roadmap — with effort estimates and dependencies
- What we need — budget, hiring, decisions from leadership
- What we're saying no to — and why
Sprint Discipline
- Build team: 2-week sprints. Every sprint has a goal. Every sprint closes.
- Sprint demos every 2 weeks — leadership can attend
- Mid-sprint requests go to backlog unless P1
- Run team handles all urgent mid-sprint requests
Communication Cadence
| Audience | Frequency | Format |
|---|---|---|
| Executive team | Monthly | Written status + live Q&A |
| Marketing team | Weekly | Standup or async update |
| Full company | Quarterly | Tech roadmap review + demo |
| During events | Real-time | Dedicated Slack channel w/ Run team lead |
Change Management for the Executive Team
The hardest change isn't technical — it's behavioral:
- Stop making last-minute decisions that force fire drills. 30-day freeze before major events.
- Commit to KPIs and don't change them every 3 weeks. The data lake is useless if what you measure keeps shifting.
- Trust the process. If Sprint 4 says Feature X ships, it ships in Sprint 4 — not tomorrow because someone panicked.
- Budget for run, not just build. Operations costs money. That's not waste — it's the cost of keeping lights on while you build the future.
What I Recommend We Do Together
Phase 1: March UPW (Now → March 12)
- Set up load testing + run full pre-event simulation (30K+ sessions, global, real browsers)
- Implement continuous synthetic monitoring on all customer-facing pages
- Validate checkout end-to-end: Apple Pay, Google Pay, EU, mobile, ad blockers
- Implement direct email sending (bypass HubSpot for transactional emails)
- Deploy optimized landing page via Cloudflare for UPW traffic
- Build 2-3 real-time event dashboards
- Enable Klarna and European payment methods in Stripe
- Publish pre-event confidence report to leadership
Phase 2: Restructuring + AI Upskill (March → April)
- Present Build vs. Run recommendation to executive team
- Map existing team members to new structure (Spork → Run, Justin → Build)
- Run AI Engineering Flow workshop with Cole Medin ($20K) — upskill entire engineering team
- Conduct AI agent audit — inspect current roadmap for agent opportunities
- Evaluate remaining hiring needs after agent deployment plan
- Establish quarterly planning cadence
- First quarterly roadmap session
Phase 3: Tony Robbins OS + Growth (Q2-Q4)
- Executive requirements workshops — define what each department needs from the OS
- Justin leads product roadmap for TROS — phased build plan
- Map current org chart → create AI Org Chart vision → plan AAA phases
- Build and deploy first AI agents (monitoring, integration, QA, reporting)
- Guide Salesforce rationalization and Heroku migration
- Design and launch Mastery Path + Event Passport products
- Reposition Tony AI as connective tissue across all products
- Begin TROS backstage dashboards — executive and events interfaces first
- Advisory role: monthly check-ins, architecture reviews, vendor evaluations
Landing Page Proof of Concept
We already rebuilt the UPW landing page as a demonstration:
- Original (HubSpot): go.tonyrobbins.com/march-upw — slow, render-blocking scripts, heavy DOM
- Optimized (Cloudflare): upw-landing.pages.dev — sub-second load, static, edge-cached globally
The Cloudflare version is an exact visual replica with all CSS inlined, fonts preloaded, images served from CDN, no render-blocking JavaScript, and served from 300+ edge locations.
Known limitation: The Stripe checkout widget has a CSP frame-ancestors whitelist that only allows embedding on specific domains: tonyrobbins.com, go.tonyrobbins.com, *.hubspot.com, *.hs-sites.com, *.hubspotpagebuilder.com, and timetorisesummit.com. Any non-whitelisted domain (including our Cloudflare Pages deploy) is blocked — the checkout drawer opens but the iframe refuses to load. This proves the architectural fragility: the checkout is domain-locked, requiring either whitelist addition or a rebuild as a direct Stripe Payment Element (recommended in Part 2A).
This dual-deploy approach can be applied to any sales page before major events.