The path to "#1 in Trinidad by 2028" — month by month, week by week, with a clear owner for every deliverable.
Each month has a clear goal, deliverables with an owner (a real person, not "the team"), and the dependencies that need to be resolved before or in parallel.
The 2028 goal isn't tackled in one leap. It's tackled by opening the marketplace in controlled phases — 10 champions → 55–60 sellers → scale — while building the system (processes, content, support) that will sustain that growth without burning out the team.
| Deliverable | Owner | Notes |
|---|---|---|
| Share the 33-lead list with Pablo | Whoever has the list today | Blocker — nothing else in this block starts without this |
| Prepare Excel + upload 33 contacts to HighLevel with tags (Stage/Profile/Priority) | Pablo | See Onboarding SOP, Part A — Stage 0 |
| SOP for bug/improvement reports to Wappsi documented and shared | Pablo | See Wappsi SOP |
| SOP for product photo verification (new arrivals) documented | Laura + Joel | See Product QC SOP |
| Formal question to Wappsi: SLA for responding to improvements/bugs | Pablo | Tomorrow 07/16 — see Wappsi SOP, ticket #4 |
| Request to Wappsi: automatic "Out of Stock" visual label at 0 units | Pablo | See Wappsi SOP, ticket 1.b |
| Roadmap kickoff presented to the team | Faiber | See Kickoff Script |
| Monthly + weekly marketing planner | Tevin | Already his function — integrated into the roadmap, not a new task |
| Deliverable | Owner | Notes |
|---|---|---|
| Initial contact with first 5–6 already-tagged leads begins | Sasha / Rosannah | See Onboarding SOP, Stage 1 |
| Verification of first accounts created | Pablo / Sydney | Final approval authority |
| Payout + package configuration + first products of that initial batch | Assigned CSR | Guide the seller, don't create the product for them |
| Email drip campaign (10 emails) built and loaded into HighLevel | Kriston | See Email Drip document |
| Basic platform process documentation | Kriston | Document what he builds in HighLevel/automations — feeds Email Drip resource |
| Wappsi SLA response received and communicated to the team | Pablo | Closes ticket #4 |
| Deliverable | Owner | Notes |
|---|---|---|
| Onboarding continues — second batch of 5–6 leads | Sasha / Rosannah | Pilot pace: 5–6/week |
| First anchor seller testimonial recorded | Ian + Tevin | 2–5 reels/month is this duo's goal |
| Google Business Profile created + first reviews requested | Kriston | Already validated in Master Strategy Doc |
| First product photo QC check on "New Arrivals" | CSR on duty + Laura | See Product QC SOP |
| Deliverable | Owner | Notes |
|---|---|---|
| Onboarding continues — third batch (≈18–20/33 completed) | Sasha / Rosannah | Pilot pace maintained |
| Weekly team checkpoint | Tevin (coordinates) | Part of the defined reporting rhythm |
| Month 1 close — bi-weekly report #1 to Faiber | Tevin (coordinates) | First formal roadmap review point |
| Second anchor seller testimonial published | Ian + Tevin | Completes the month's goal of 2 testimonials |
| Deliverable | Owner | Notes |
|---|---|---|
| Onboarding pace increases to 8–10/week | Sasha / Rosannah + Pablo/Sydney | See Onboarding SOP — pace goal |
| WhatsApp support active for new sign-ups | CSR on duty | Channel already validated in Channel Map |
| Google Search Ads active (high-intent keywords) | Kriston | E.g., "how to sell online in Trinidad" |
| Weekly checkpoint | Tevin (coordinates) |
| Deliverable | Owner | Notes |
|---|---|---|
| Onboarding of all 33 closed (goal: 33/33 complete) | CSR + Pablo/Sydney | End of estimated 4–5 week window |
| First success story published (seller with real sales) | Kriston + Tevin | Social proof for Phase 2 |
| Review of open tickets with Wappsi | Pablo | Report results to Faiber |
| Bi-weekly roadmap progress report #2 | Tevin (coordinates) | Weekly checkpoint + report every 2 weeks |
| Informal go/no-go decision to open Phase 2 in Month 3 | Faiber | Based on actual pilot onboarding results |
| Deliverable | Owner | Notes |
|---|---|---|
| Tagging new batch in HighLevel | Kriston | SOP already exists from Phase 1 |
| Launch radio campaign (Hott 93, RED 102, WACK 90.1FM) | Kriston | Targeting 35+ demographic |
| Outdoor activations (events, pop-ups) | Ian + Tevin | Community presence to recruit sellers face-to-face |
| Billboard campaign | Kriston + Tevin | Key Trinidad locations for brand awareness |
| Aggressive YouTube campaign | Ian + Tevin + Kriston | Seller stories, product showcases, marketplace how-tos |
| Payment provider partnerships | Kriston + Tevin | Expand payment options beyond current setup |
| Referral program design ("bring a seller, get a free month") | Tevin + Kriston | Mechanics approval via Faiber |
| Full channel performance review — reallocate budget based on actual CPA | Kriston | With data from Months 1–2 |
| Deliverable | Owner | Notes |
|---|---|---|
| Consolidate onboarding pace at 8–10/week sustainably | CSR + Pablo/Sydney | With Phase 2 volume |
| Evaluate need for a third support person for sellers | Laura | Validate with actual volume data |
| Start B2B outreach to Shopify owners (prep Phase 3) | Kriston | Cluster 4 — Established Sellers |
| YouTube campaign momentum tracking | Ian | Report views, sign-ups per channel, adjust content strategy |
| Second success story published | Kriston + Tevin |
| Deliverable | Owner | Notes |
|---|---|---|
| First KPI cut: active sellers, GMV, cold lead reactivation, NPS | Kriston | Input for Phase 3 decision |
| Formal go/no-go decision for Phase 3 | Faiber | With data, not intuition |
| Consolidated quarterly report (Months 3–5) | Tevin (coordinates) | Presented alongside the go/no-go decision |
| Deliverable | Owner | Notes |
|---|---|---|
| Automate more of the onboarding funnel (bulk upload, real self-serve) | Pablo | Reduce CSR 1:1 dependency |
| Formalize B2B/LinkedIn channel for Established Sellers (Cluster 4) | Kriston | |
| Kriston full-time confirmed — reassess Marketing Systems/BI load | Kriston + Faiber | Kriston returns full-time in August |
| Deliverable | Owner | Notes |
|---|---|---|
| Evaluate need to expand Logistics/Fulfillment team | Sydney + Laura | Based on actual accumulated volume |
| Consolidate BI dashboards — reporting is no longer manual | Kriston | |
| Second KPI cut of marketplace performance | Kriston | Compare against Month 5 cut |
| Deliverable | Owner | Notes |
|---|---|---|
| Annual team capacity vs. contracts review | Faiber + Laura | Direct input for contract renewals |
| Year-end consolidated results report 2026 | Tevin (coordinates) + Kriston | Active sellers, GMV, actual vs. roadmap progress |
| Preliminary 2027 planning | Faiber + Andrea + Kriston | Detailed month-by-month 90 days before starting |
Not detailed month-by-month yet (that would be premature); reviewed quarterly and detailed 90 days before each phase.
Consolidation as Trinidad's #1 marketplace — deepen market penetration, don't expand geography.
Brand milestone: "#1 in Trinidad." At year-end, the formal conversation about if/how to expand to the rest of the Caribbean begins.