Multi-Touch Outreach Playbook — Email & LinkedIn Sequence

Overview

This playbook defines a manual, multi-touch outreach sequence for engaging the Aviary "Top 100" prospect list. The approach was deliberately designed to be run manually first — allowing rapid iteration on messaging and timing — before being automated via ^[1]. This avoids premature investment in expensive HubSpot automation features while the sequence is still being validated.

The sequence combines email and LinkedIn touchpoints to maximize surface area with prospects across channels.

The Sequence

Step 4 — LinkedIn Comment: Optional Only

The LinkedIn comment step must be treated as conditional, not automatic. Many target executives in this space are self-described "lurkers" — they scroll and consume content but do not post. Commenting on a post that is six months old (or nonexistent) wastes effort and can appear tone-deaf.

Rule: Only execute Step 4 if the prospect has posted on LinkedIn within the last 30 days. Active posters tend to respond well to engagement; non-posters will not notice it.

"A lot of the executives, like, how do you guys use LinkedIn? They're like, we're lurkers. We scroll and we learn, but we don't post." — Aaron Grossman

Rationale

• Manual-first: Testing the playbook manually allows the team to observe what works before locking logic into automation. Sequence timing, messaging, and channel mix can all be adjusted quickly without touching code.
• Avoid HubSpot costs: HubSpot charges incrementally for automation features. By using ^[1] (already licensed) once the playbook is validated, the team avoids those costs entirely.
• Automation endpoint: Once the sequence is confirmed to be working as intended, the full flow will be built in N8N. Prospect engagement signals (website visits, form fills, link clicks) will trigger notifications for Aaron to follow up personally.

Supporting Infrastructure

Prospect List

• Source: HubSpot "Top 100" segment (91 contacts)
• Uploaded to ^[2] for real-time activity tracking (funding rounds, hiring signals, etc.)
• See: ^[3]

Email Platform

• Tool: ^[4] (seat to be provisioned by Justin)
• Integration: SendGrid connected to HubSpot to maintain a single source of truth for all prospect communication history
• Backup log: A Google Sheet will also record every sent email as a redundant audit trail
• Template: HTML email template to be designed by the design team (Sebastian coordinating)

CRM

• ^[5] serves as the system of record for prospect history
• SendGrid activity synced back into HubSpot contact timelines

Action Items

• [ ] Mark — Draft the full playbook document (steps, timing, message templates) and share with Aaron for review
• [ ] Mark — Send Aaron Sales Navigator upload instructions + pre-exported HubSpot "Top 100" file
• [ ] Aaron — Upload "Top 100" list to Sales Navigator upon receipt
• [ ] Aaron — Message Justin to provision a SendGrid seat
• [ ] Sebastian — Brief designers on HTML email template requirement
• [ ] Sebastian — Build out the drip campaign in SendGrid once template is ready
• [ ] Mark — Implement validated playbook in N8N once manual testing confirms the sequence works

Related

• ^[3]
• ^[1]
• ^[4]
• ^[5]
• ^[2]
• ^[6]
• ^[7]