⚖️ Awaiting exec sign-off

Pending decisions

Jessica-framework structured: the ask, the context, the options, a recommendation, and who's blocking. Surfaced here so nothing sits in a Slack thread waiting to be rediscovered.

⚖️ Pending Decision

Replit Enterprise — approve?

The ask

Approve ~$20K/yr + $100/mo per seat for ~10 dev licenses to stand up Replit Enterprise for the RevOps + AI build layer.

Context

Replit is already the host for every RevOps automation we've shipped (Deal Execution Score, Upsell Detector, Golden Script scorer). Enterprise tier unlocks non-usage-based pricing + team admin + SSO, which is required as we scale adoption across Sales + CX.

Options
  • Approve Enterprise ($20K/yr base + $100/mo/seat)
  • Stay on Pro tier (per-seat, usage-based, unpredictable)
  • Migrate production workloads to Railway and skip Enterprise
Recommendation

Approve Enterprise. ROI frame: every custom automation ships without an engineering ticket. Even 2-3 additional RevOps builds this quarter pays for the seat cost.

Owner
Kevin + Ian (proposers) · Nick + Jessica (approvers)
Blocked on
Finance review
Deadline
End of Q2 2026
⚖️ Pending Decision

Outreach tooling investment — finalize

The ask

Close the pending Outreach review + align the engagement stack with broader GTM roadmap.

Context

Outreach is our current sales engagement platform. Documented review exists in the RevOps Notion page but hasn't been resolved. Open question: renew, consolidate, or rip and replace.

Options
  • Renew as-is
  • Renew with reduced seat count + consolidate
  • Evaluate replacement (Salesloft, Apollo, HubSpot native)
Recommendation

Renew with reduced seat count. We underutilize rep activity sync back to HubSpot; consolidating seats gives us ROI headroom to evaluate alternatives in H2.

Owner
Kevin
Blocked on
Sales leadership input on seat count
Deadline
Before renewal window (check contract date)
⚖️ Pending Decision

GTM Brain GitHub repo — exec sign-off

The ask

Approve the shared GitHub repo as canonical AI agent context — Nick + Melissa need to sign off on brand voice + product positioning.

Context

Ian is standing up a RevOps GitHub repo that acts as the 'brain' every AI agent reads from. Needs exec sign-off on the brand + positioning markdown so agents don't drift.

Options
  • Sign off on current draft
  • Request revisions (comment in repo)
  • Require formal brand review before using in production
Recommendation

Sign off on v1, iterate in-place. Cost of waiting is that each agent re-invents voice.

Owner
Ian
Blocked on
Nick + Melissa review
Deadline
Next 2 weeks
💡 The Jessica template

Every pending decision on this page follows the Problem → Benchmarks → Metrics → Andon → Solution → Tradeoffs → Feedback structure. BLUF every time.

Trust builder: surface problems proactively — don't wait for 1:1s. Trust eroder: vague answers or half-baked solutions. This page is the proactive surface.