Build a Proposal-Sent Auto-Follow-Up Workflow

You are a sales-ops automation engineer for digital marketing agencies — every workflow you build is paste-ready into Zapier/Make/HubSpot Workflows and uses production-grade error handling.
Agency: [AGENCY_NAME] — [SERVICES] | CRM: [CRM_TOOL] | Automation tool: [AUTOMATION_TOOL] | Email sending tool: [EMAIL_TOOL] | Proposal tool: [PROPOSAL_TOOL] | Trigger: [TRIGGER_EVENT] | Cadence: [CADENCE] | Stakeholders to notify: [STAKEHOLDERS]
Design a follow-up automation that fires when a proposal is sent, drafts 3-4 sequenced touches at increasing intervals, sends from the rep's inbox (not generic), and auto-pauses on any reply, meeting booked, or stage change.

- Every step has action, tool, inputs, outputs, conditions
- Drafts only — touches must be queued for rep approval, not auto-sent, unless [AUTO_SEND]=true
- Cadence variables: day 2 nudge, day 5 value-add, day 9 break-up
- Listen for reply / meeting / stage change → halt immediately
- Include error / fallback path if email API fails
- No actions that risk sending spam (max 4 touches, hard stop)
- Personalization tokens pulled from CRM + proposal data

Output as: Trigger | Step 1..N | Cadence Table (day / channel / template / personalization tokens) | Halt Conditions | Error Handling | 3 Sample Email Drafts. Paste-ready into [AUTOMATION_TOOL].

• [AGENCY_NAME] — Your agency name
• [SERVICES] — Service lines
• [CRM_TOOL] — Your CRM
• [AUTOMATION_TOOL] — Workflow platform
• [EMAIL_TOOL] — Gmail, Outlook, HubSpot Sequences, Salesloft
• [PROPOSAL_TOOL] — PandaDoc, Proposify, DocuSign, Better Proposals
• [TRIGGER_EVENT] — e.g., Proposal 'Sent' status webhook
• [CADENCE] — Day offsets and message intents
• [STAKEHOLDERS] — Rep + manager on stalled cycle
• [AUTO_SEND] — true = auto-send, false = draft for approval

Agency: Spark & Stone — branding + paid social | CRM: HubSpot | Automation tool: Zapier | Email tool: Gmail | Proposal tool: PandaDoc | Trigger: PandaDoc webhook 'document_state_changed' = sent | Cadence: Day 2 nudge, Day 5 case study, Day 9 break-up | Stakeholders: Rep DM + manager DM at day 9 | Auto-send: false (drafts only)

TRIGGER: PandaDoc webhook 'document_state_changed' = sent.
Step 1 — Lookup HubSpot Deal by proposal recipient email.
Step 2 — Update Deal stage → 'Proposal Sent', set proposal_sent_at = now.
Step 3 — Schedule Day 2 task in Zapier Delay.
Step 4 — Day 2: check Deal for reply/meeting/stage change → if any, halt. Else, draft email in Gmail from rep's account with template T1 (nudge). Slack DM rep to review + send.
Step 5 — Day 5: same halt check, draft T2 (case study tied to prospect industry).
Step 6 — Day 9: same halt check, draft T3 (break-up). Also DM manager.
CADENCE TABLE: D2/Email/T1 nudge / {firstname, proposal_link, top_question}; D5/Email/T2 case study / {industry, case_study_url}; D9/Email/T3 break-up / {firstname, soft_close}.
HALT CONDITIONS: reply received | meeting booked | deal stage moved | deal lost.
ERROR HANDLING: Gmail API fail → retry 3x, then Slack rep with template to send manually.
3 SAMPLE DRAFTS:
T1: 'Hi Sarah — wanted to check the proposal made it through and answer any questions on scope or timeline. Want me to walk you through the social plan live?'
T2: 'Hi Sarah — one we just wrapped with [similar brand] hit 3.2x ROAS in 60 days. Quick teardown attached. Useful for your team's review?'
T3: 'Hi Sarah — should I close out this proposal on my end or keep it warm? Either is fine, just don't want it lingering.'

• Drafts > auto-send for high-ticket retainers — reps catch personalization gaps and the prospect can't tell it's templated
• Pull the prospect's top question from the discovery call notes into the day-2 draft — instant lift in reply rates
• Track 'days from proposal sent to next reply' as a workflow KPI; if it doesn't drop after 30 days, your templates are the problem