Breakmark Roadmap
May → November 2026

Post-meeting plan • Mat + Brad + Jackson, 2026-04-30

August must-ship: Egypt-direct + Website refresh 5 external blockers 48 tracked items
v1.1 · 2026-05-01
Click any item to drill in
Phases
7
May → Nov+ 2026
Tracked Items
48
across all phases
Dev Days Total
~146
uninterrupted build time
Calendar Days
~378
incl. reviews + soak
External Blockers
5
Terry, Mico, Ellen, Taylor, vendors
Hard Deadlines
7
3 in August alone

★ Critical Path

Terry approval → Egypt-direct backend → Egypt UI → Egypt cutover  |  In parallel: Website refresh (Brad's mid-Aug deadline, no DB risk). Everything else descopes if Terry punts.

Hard Dates

May 1
Sequencing digest to Mat
Owner: Jackson
May 1
RollerCon QR redirect live
Brad / ad due
~Jun 15
Designer interviews complete
Gates Drive + workflow build
Early Jul
AfterShip renewal decision
Group; depends on Mico
Jul 15
Designers in backend (ideal)
Brad's preferred
Aug 1
Designers in backend (latest)
Brad's hard latest
~Aug 15
Customer website live
Brad's true deadline

Phase Timeline

May'26
Jun'26
Jul'26
Aug'26
Sep'26
Oct'26
Nov'26
P0 — Derisk + Dispatch
This
P1 — Foundation
May
P2 — Build Heavy
June
P3 — Integration + Designer Prep
July
P4 — Cutover
August
P5 — Consolidation + Scale Prep
September
P6 — Looming Chaos / Multi-Tenant
November

Phase Detail

Phase 0 · This Week (May 1 – May 7)

Derisk + Dispatch

Quick wins. Unblock external dependencies. Ship the digest.
active
9
items
2.8000000000000003
dev days
~10
calendar days
Phase 1 · May (week 2 – 4)

Foundation

Merge unmerged work. Spike Egypt arch. Lock vendor decisions.
queued
7
items
17
dev days
~44
calendar days
Phase 2 · June

Build Heavy

Egypt backend. Website prototype. Production automation.
pending
8
items
28
dev days
~72
calendar days
Phase 3 · July

Integration + Designer Prep

Clerk on COM. Designers onboard. AfterShip exit.
pending
8
items
26
dev days
~65
calendar days
Phase 4 · August

Cutover

Egypt live. Designers cut over. Website ships. Inbox v1.
high-risk
6
items
25
dev days
~62
calendar days
Phase 5 · September – October

Consolidation + Scale Prep

Builder full. Drive migration. POS evaluation. Captain portals.
pending
6
items
28
dev days
~79
calendar days
Phase 6 · November +

Looming Chaos / Multi-Tenant

Terry equation. External customer ready. Comms automation full.
future
4
items
19
dev days
~46
calendar days

External Blockers · Cannot Sequence Without These

Owner: Mat

Terry approval — cut NC

Gates entire Egypt-direct architecture. Until known, design must support both paths (NC-in fallback adds lag).

Blocks: 2 items
Owner: Jackson chasing Mico

ShipStation tracking parity (G1–G3)

G1–G3 gates from memory project. If G3 = no, full v1→v2 label refactor required (multi-week).

Blocks: 2 items
Owner: Jackson

Designer interview · Ellen

Defines Drive replacement scope. Blocks Phase 2 art-checker finishing + workflow design.

Blocks: 2 items
Owner: Mat → Taylor

Branding files

Gates website concept work. Mat connecting to set deadline.

Blocks: 1 item
Owner: Mat

Vendor backend tours

Feature wishlist input for Egypt UI design. Next 2 weeks.

Blocks: 1 item

Effort Allocation by Track

Egypt-direct
23d
Builder
16d
Multi-tenant (Terry)
12d
Quick wins
11.8d
Website refresh
11d
Designer workflow + art-checker
10d
ShipStation
9d
Inbox + Trello displacement
9d
Captain portals
9d
Drive replacement + migration
8d
Clerk migration
7.5d
Stripe deeper integration
7d
Order-status cleanup + bugs
6.5d
Customer comms automation
6d

Risk Dashboard

Terry says 'no' to NC cut

critical

Egypt-direct architecture must accommodate NC middleman. Adds queue lag, PO sync layer, accounting splits.

Builder August slip

expected

Greenfield UI. ~16 dev-days. No existing Builder code in repo. Recommend P5 (Sept-Oct).

Drive 7.5TB migration window

high

Two distinct projects: (1) build storage UI ≠ (2) physical 7.5TB move. Mat collapses these. Bandwidth-bound.

ShipStation G3 = no

medium

Forces v1→v2 label refactor. Multi-week. AfterShip stays. Decision deadline early July.

Hasura role coverage gaps

medium

New Egypt + designer roles must include every column referenced by every .gql query. Per memory feedback.

Clerk admin scope creep

medium

If migration extends to admin (not just COM customer), 2-3x effort. Recommend phased: customer side first.

Designer disruption pre-Aug

mitigated

Mat: no workflow changes till late Jul / early Aug. Background work only till then.

Pete (customer w/ admin)

trivial

Role demote in P0. Kills email noise to him.

Two Alexis identities

mitigated

Mat bridged @greaterboston / @inxpress threads. Reply-all going forward.

Action Items by Owner

JT
Jackson · 13 items

  • 1Implement Clerk (full auth replacement)
  • 2Detail Clerk recap doc
  • 3Modernize backend dashboard libs (PR #470 merge)
  • 4Tighter Stripe integration (tax refund, sync)
  • 5Interview designers (Ellen, others)
  • 6Review design workflow w/ Ellen
  • 7Sequence implementation plan + estimates
  • 8Send Mat-facing digest (May 1)
  • 9Schedule meeting w/ Alan
  • 10RollerCon QR redirect
  • 11Fix Check Orders pending tab rename
  • 12Update paid-tab query logic
  • 13Enable coupon edit/delete (with usage guard)

MG
Mat · 6 items

  • 1Show Jackson vendor backends (next 2 weeks)
  • 2Confirm Terry approval on cutting NC
  • 3Validate Terry + Egypt receptive to system
  • 4Acquire branding files from Taylor
  • 5Improve checkout promotion ideas
  • 6Decide AfterShip renewal (group, by July)

GR
Group · 3 items

  • 1AfterShip renewal decision by early July
  • 2Validate Terry requirement
  • 3Customer-facing automated emails (separate meeting)