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A sequence is a series of emails sent automatically on a schedule: an opener, then one or more follow-ups spaced days apart. Enroll people once and HelloSky handles the sending, stops the moment someone replies, and shows you exactly where every person stands. Sequences live on the Outreach page: the Overview tab has a Sequences panel listing every sequence in your organization with its owner, enrollment counts, and reply rate.

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Create a sequence

On Outreach → Overview, click New sequence and choose how to start:
  • Generate with AI: describe the role (or paste a job description or posting URL), and get a complete, editable sequence.
  • Write it myself: start from a blank editor.
Either way you land in the sequence editor:
The sequence editor with a step, merge fields, the AI personalization toggle, and a live preview
  • Each step has a subject, a body, and a delay in days after the previous step. Follow-up steps are delivered as replies in the same thread as the opener.
  • Use the Insert chips to drop in merge fields: First name, Full name, Company, and Title fill in per recipient at send time. The Preview panel shows the result with sample data.
  • Check Personalize each email with AI on a step to have HelloSky write a unique email per recipient from their profile; you approve every one before it sends (see Guardrails & approvals).
Click Create sequence and it’s ready to enroll people into.

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Enroll people

The fastest path is from a saved people list:
  1. Open the list and select the people you want to contact.
  2. In the bulk actions bar, click Add to sequence and pick the sequence.
You can also enroll a single person from the Sequence button on their profile. Enrollment is capped at 1,000 people per batch. Before anything is enrolled, HelloSky shows you whether a teammate has already contacted or enrolled each person, so the same candidate doesn’t hear from two people at your firm. The warning is informational; it never blocks you. People we have no email address for can’t be enrolled: they are skipped and reported back to you, along with anyone who was already in the sequence.

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Track and manage enrollments

Open a sequence to see its Enrollments: every person in it, which step they’re on, their status, and when their next email goes out.
A sequence's enrollments with statuses, current steps, next send times, and pause/stop actions
You can pause, resume, or stop individual people without touching the rest of the sequence, and filter by status to focus on what needs attention.
Reply detection is automatic. The moment someone writes back, their remaining follow-ups are cancelled, so there’s no risk of an automated “just bumping this” landing after a real conversation has started.

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Archive a sequence

Archiving a sequence from its detail page stops its scheduled sends and prevents new enrollments. Past sends and threads remain visible.