RegScale Handoff Kit · 05 of 06 · v1

What You Need To Do Yourselves — The Human Side of the Chain

A boundary card. Cowork drafts; you decide, approve, and verify. This artifact names the boundary explicitly so the work that's yours stays yours.

Audience: Esty, Brittany, Morgan, Amanda, Alex, Elyse Time to read: ~5 min Time to remember the boundary: indefinite Link styles: blue = Monday Doc · orange = live URL · yellow = cowork kit zip
TL;DR

What this is: the inverse of a Cowork capability sheet. This card names what stays human in the AI-native motion. The v6 motion artifact frames it cleanly: "AI does the heavy lifting on what's clearly specified. Judgement gets spent on the parts that actually need it: strategic calls, partner relationships, creative decisions, the moments only the person in the seat can make." How to use it: when you're about to delegate something to Cowork and a small voice asks "wait, should I be doing this?" — scan section ② for your seat, scan section ③ for whether it's a judgment moment, decide accordingly.

①

The boundary — Cowork drafts, you decide

Two columns. Same chain, two responsibilities. The chain runs because both halves do their work.

What Cowork generates (the heavy lifting)

The drafts and the records

  • Asset drafts — email body content, landing page copy, ad set, deck slides, day-of execution kits, analyst one-pagers — anything that hydrates from a JSONB instance + Asset Spec template
  • Substance + style check records — the substance check (against the GTM Messaging Book) and the style check (against the voice guide) run as part of the work and get attached to the Monday subitem
  • Cross-asset consistency — when the May 5 date moves, every asset that referenced it re-renders from the single JSONB source
  • State transitions — Workshop Status moves from Drafting → Ready for Review automatically when Cowork pushes a draft back
  • Provenance — every asset carries a record of which SOP version it ran against, which proof points it cited, which voice guide version it scored against
  • Lookback / repurposing drafts — SW-05 follow-up artifacts (resource page, replay blog, post-event recap email)
What you decide / approve / verify (the judgment)

The calls only you can make

  • Strategic calls — why-anything / why-now / why-us at SW-01; audience segment + persona priority; pillar selection; channel commitments
  • Voice Pass approval — the PASS / FAIL / CONDITIONAL decision at SW-01 review; Cowork's Quick-Scan output is input, not verdict
  • Tier classification — Webinar / Tier 1 / etc. at SW-00; tier determines budget + cadence + governance
  • Partner relationships — Carahsoft, FS-ISAC, Gartner; the human relationship layer Cowork has no signal for
  • Design intent — brand color, typography, layout choices; the design eye that's earned its trust
  • R&R closure decisions — at QG-5; the call to file or postpone the post-event Report & Review (the gate the FedRAMP 20x failure mode crashed through)
  • Verification — Cowork's draft is right enough to ship vs. needs another round; this is the operator's eye on the page
The shape of the question matters. Bolting AI onto existing work would ask "how do we make this faster?" Rebuilding work to be AI-native asks "what would this process look like when the spec is tight enough for AI to run it?" The first answer saves time. The second changes what's possible. — v6 GTM motion artifact, "What would shift, if this is adopted"
provenancev6 GTM motion artifact § "What would shift" + § "A typical cycle — pull, run, push" → kit/v6-ai-native-gtm-motion.html · grounded in the Workshop Sandbox board April 29 chain (Cowork drafted; role-holders reviewed)
②

Your seat — what each of the six anchored roles owns

For each role, what's yours to decide and what Cowork does for you. Drawn from the canonical Role Holders FY26 and your own workshop assignment cards in the kit zip.

Slot 1 · brand gatekeeper

Esty Peskowitz

VP of Marketing · Brand Authority · Messaging Authority

What stays yours
Strategic brief authoring (SW-01: why-anything / why-now / why-us); Voice Pass approval (PASS / FAIL / CONDITIONAL on every external-facing asset); SOP escalation regardless of category; pillar selection per campaign; partner relationship calls; brief approver for all campaigns. Quick-Scan ≤ 2 min; the call is yours, not committee's.
What Cowork does for you
Drafts the brief in canonical SW-01 format from your inputs; runs the substance check; runs the style anti-pattern gate (the count + show-stopper detection feeds into your Quick-Scan); auto-appends Voice Pass records to the audit log. kit/workshop-assignments/01-cmo-esty.md
Slot 2 · primary asset author

Amanda Greenspan-D'Souza

Field Marketing Operations · ~81% of Active Marketing Programs board activity

What stays yours
Cross-team coordination (you're the operational hub); content judgment on which proof points fit which audience; the operator's eye on Cowork's draft — "is this right enough to ship, or does it need another round?"; HubSpot list segment selection; SF campaign association decisions.
What Cowork does for you
Drafts the T-14 / T-7 / T+1 email cadence body content from kit/data/sans_email_*.json; drafts landing page copy; ensures cross-asset consistency (May 5 in the email matches May 5 in Elyse's ad headline because they both pull from the same source). Kills the "second-guess whether it's good enough" friction by shipping the Voice Pass live. kit/workshop-assignments/02-fmops-amanda.md
Slot 3 · paid media

Elyse Hoekstra

Paid Media Contractor · LinkedIn Campaign Manager + Sales Navigator + Google Ads

What stays yours
Audience targeting setup (LinkedIn segments, Sales Nav lists); paid media performance reads + budget allocation; the call on whether to activate paid LinkedIn boost (per Webinar Lifecycle SW-03's conditional activation — when registration velocity falls below threshold); creative direction for ad sets.
What Cowork does for you
Drafts the 300×250 ad creative + the LinkedIn paid post copy from the locked SW-01 brief and the verbatim proof points (so the ad headline grounds in the same line that the email body uses, no coordination required). Generates IAB-size variants from one source. kit/workshop-assignments/03-paid-elyse.md
Slot 4 · brand + design · backup gatekeeper

Morgan Johnson

Brand & Design Lead · backup for SW-01 Voice Review when Esty is occupied

What stays yours
Design intent decisions — brand kit choices, color, typography, layout integrity; the design eye on every visual asset; voice review when Esty is occupied (same Quick-Scan procedure); the *"can I edit this directly"* call on AI-generated visuals (per the recap, the answer is yes — pull SVG, edit manually, push back).
What Cowork does for you
Drafts deck slides from the brief + proof points (e.g., the "Why Us" slide 9 with three verbatim Register proof cards); generates ad creative variants in SVG so you can edit at code level rather than dragging design files between tools. kit/workshop-assignments/04-design-morgan.md
Slot 5 · field marketing lead

Brittany Gleason

Field Marketing Lead · campaign Monday item PM · commitment + tier classification at SW-00

What stays yours
Tier classification (Webinar / Tier 1 / etc. — drives the entire downstream cadence); commitment decisions (this event, that partner, this date); the operational alignment work — *"defending why certain programs were chosen, multiple stakeholders sign off with no clear goal defined"* — that's your call, not Cowork's; quarterly + regional plan structuring.
What Cowork does for you
Drafts the SW-04 day-of execution kit (run-of-show timing, dial-in coordination, speaker prep checklist) from your inputs; drafts status-update digests from Monday subitems + HubSpot metrics (so the *"work about work"* of status reporting is an authoring + review pass, not a from-scratch write). kit/workshop-assignments/05-fmlead-brittany.md
Slot 6 · product marketing

Alex White

PMM Lead · competitive positioning · technical content drafting · Messaging Book backup gatekeeper

What stays yours
Competitive positioning calls (Wiz / Drata / Vanta differentiation); analyst engagement strategy (Gartner / Forrester / IDC); technical content judgment (SOC 2 vs. FedRAMP nuance); product/category authority on Messaging Book contributions; substance gate when Esty is occupied.
What Cowork does for you
Drafts the SW-05 post-event analyst briefing one-pager (audience: BDR Josh's qualified PoC leads); drafts data-sheet variants from product team intel; cross-references the GTM Messaging Book Differentiation file so the same competitive line shows up consistently across assets. kit/workshop-assignments/06-pmm-alex.md
provenancekit/workshop-assignments/01–06 cards (per-seat scope) + Role Holders FY26 (canonical responsibilities) + Workshop Assignments — April 29 (slot mapping)
③

The five irreplaceable judgment moments

Five points in any campaign where the call is yours to make. Cowork can draft the artifact around the call, but the decision itself is human. With a clear "what happens if you delegate this" warning per moment.

1

Strategic brief authoring

Owner: Esty Peskowitz · Phase: SW-01 · Reference: SW-01 Strategic Brief

The strategic brief decides why the campaign exists, who it's for, and what proof points anchor it. Cowork drafts the brief in canonical format using your inputs — but the inputs themselves (audience, pillar choice, channel commitments, partner agreements, hero offer framing) are decisions only the operator with full context can make.

the brief becomes generic. The why-anything / why-now / why-us defaults to the closest pattern in the kit (probably FedRAMP 20x) regardless of whether that fits this campaign. Audience targeting drifts. Pillar selection collapses to whichever is most-cited rather than which best matches the actual audience.
2

Voice Pass approval (PASS / FAIL / CONDITIONAL)

Owner: Esty Peskowitz (backup: Morgan Johnson) · Phase: SW-01 Voice Review · Reference: Brand Voice SOP

Per Brand Voice SOP Key Rule 2: "Voice review decision sits with the brand gatekeeper, not committee." Cowork's Quick-Scan output is your input — the count of anti-pattern triggers, the show-stopper detection, the section-level scoring — but the PASS / FAIL / CONDITIONAL call is yours. The Quick-Scan is fast (≤ 2 min) precisely so the human call stays cheap.

voice drifts. The substance gate catches verbatim proof-point violations, but the editorial judgment ("this technically passes but reads off") is what keeps the brand sounding like RegScale. Lose that and on-voice becomes "passes a checklist," which over time becomes generic.
3

Tier classification + commitment

Owner: Brittany Gleason (Field Marketing Lead) · Phase: SW-00 · Reference: SW-00 Commitment & Tier Classification

Tier (Webinar / Tier 1 / etc.) determines the entire downstream execution shape: budget, cadence, governance overhead, status-update frequency, post-event scope. Cowork can read past commitments and suggest patterns, but the call on this commitment, this partner, this moment in the year requires operational context Cowork doesn't have.

misclassification cascades. A Tier 1 event running on webinar cadence under-resources by 3–4×. A webinar getting Tier 1 governance over-burdens the team and slows the cadence below partner expectations. Tier is small to set and expensive to fix.
4

Partner relationship calls

Owner: Esty Peskowitz + Brittany Gleason (per partner) · Phase: any cross-suite call into Speaker Session Lifecycle or partner co-marketing · Reference: Master Chain Definition § Chain 1 anchor

Carahsoft, FS-ISAC, Gartner, CSA — partners aren't tasks; they're relationships with history, sensitivity, and unwritten rules. Cowork has no signal for the difference between "Carahsoft is busy this week, postpone the ask" and "Carahsoft will be offended if we postpone." Tone, timing, and what-not-to-say are human judgment.

relationship damage. Cowork will be perfectly polite, perfectly clear, and miss every social cue. Partner co-marketing depends on trust accumulated over many small moments; a mishandled scheduling exchange can cost goodwill that took months to build.
5

QG-5 closure decision (post-event Report & Review)

Owner: Marketing Operations Lead [Jon Collette] by default · escalation to VP of Marketing [Esty Peskowitz] · Phase: SW-05 / QG-5 exit · Reference: SW-05 Follow-Up & Repurposing

QG-5 is the gate that closes a campaign. The R&R must be filed before the Monday item moves to Closed. Cowork can draft the R&R using post-event metrics (HubSpot pulls, Salesforce attribution, recording analytics) and the Webinar BOM Quality Rubric, but the call to file the R&R — vs. postpone, vs. skip — is human. The FedRAMP 20x failure mode is exactly this: the R&R was scheduled for T+33 (Dec 22, 2025) and was cancelled in March 2026.

QG-5 fails silently. The campaign Monday item never moves to Closed. The Status Update Cadence loses its closure signal. The lessons aren't filed. The next campaign doesn't benefit. Status Update Cadence's weekly checkpoint is what surfaces the drift if R&R ages past T+30 — but only if the human owner notices the prompt and acts.
provenancev6 GTM motion artifact § "What would shift" (the four named judgment categories: strategic calls, partner relationships, creative decisions, in-the-seat moments) → Webinar Lifecycle SOP suite (SW-00 through SW-05 phase ownership) + Brand Voice SOP Key Rule 2 (gatekeeper-not-committee) + Master Chain Definition § Chain 1 worked-example (FedRAMP 20x R&R failure mode) → Master Chain Definition + Brand Voice SOP