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TOOL HOW-TOOctober 23, 20267 min read

How to Use Woodpecker to Run Condition-Based Cold Email

JH

By Joris van Huët

Enterprise Interim CMO & Marketing Leader · 15+ years · 50+ orgs

Published

2026-10-23

The short answer: connect your mailbox and add warm-up, point a custom tracking domain at Woodpecker, then build the campaign path with steps and YES/NO conditions, set delivery times and a modest daily enroll, add prospects, switch on the unsubscribe options and click Run.

Disclosure: I may earn a commission through some links on this site. It does not change what this page says.

Woodpecker's onboarding is short: the app shows a checklist in the corner of every new campaign draft and ticks items off as you go. The decisions that matter sit in the settings the checklist does not force, such as daily enroll and tracking. For the product and its prices, see the Woodpecker glossary entry.

Groundwork

  • An account. The trial lasts 14 days or 500 cold emails, whichever ends first, with no card, per the pricing FAQ. The smallest paid tier is $39 a month for 5,000 emails on monthly billing (checked on 23 October 2026).
  • A mailbox on a domain you control. Woodpecker connects Google and Microsoft natively and most other providers over IMAP and SMTP.
  • A daily volume in mind. Woodpecker's daily limit article recommends 25 to 35 emails per mailbox per day and advises against more than 50. If your target needs more, plan more mailboxes, not more mail per box.
  • A lawful list. The European Commission's answer on marketing with data received from a third party expects you to tell people, at the latest in your first message, that you hold their data and will use it for marketing, and to respect anyone who objected. Cold email rules vary between countries; check the ones you send to.

1. Connect the mailbox

Go to Settings and click Add Email Account, or click Connect email under a campaign's name. For Gmail, the connection article describes a one-click integration that asks for access to read, send and manage your mail. Set the From name and signature, save, and look for the "Testing your email connection" message in your inbox: it confirms the link works.

2. Add warm-up

Open the Warm-up tab under the email account and click Add warm-up. Choose Mailivery or Warmy, then enter an app password for Google or the SMTP and IMAP details for other providers, as the warm-up article explains. Both providers start with a few emails a day and climb to 50 a day by default. Each plan includes free warm-up slots, and extra slots cost $5 a month.

3. Set a custom tracking domain

By default, open and click tracking and the unsubscribe link point at a generic Woodpecker domain. The tracking domain article has you add a CNAME record pointing your chosen subdomain at lime.wcheck.org, wait some hours for DNS, then enter the subdomain under Settings, Email Accounts, your mailbox, Sending, Custom Tracking Domains. Links then match the domain of the sending address. Check the article before you add the record, because the CNAME target may change.

4. Create the campaign

A new account opens on three choices: an AI Agent draft, a sample campaign, or a manual build, per the onboarding article. Whichever you pick, read the copy before you run it. The editor has four tabs: Sequence for the path, Workflows for routing prospects by response, Settings, and Summary.

5. Build the path: steps, follow-ups and conditions

Click Step 1, write the subject and body, and paste from a plain-text editor rather than Word; the editor article warns that formatted text may render badly, and offers a Reset formatting button. Insert snippets from the toolbar for personalisation, with fallbacks for missing data.

The plus icon below a step adds a follow-up or a condition. A condition creates a YES path and a NO path on an open, a click, a task, a snippet value or a LinkedIn connection request. The new editor allows up to 16 steps, and the default delay between steps is two days, counted from each prospect's previous email. A reply stops the follow-ups for that prospect.

Set delivery times per email with the Schedule icon: the days, the hours and up to three sending windows a day.

6. Set daily enroll and the mailbox limits

Daily enroll is the number of opening emails a mailbox sends per day in this campaign. It defaults to 50, applies to each mailbox separately, and is capped by the mailbox's own daily sending limit. With ten mailboxes and an enroll of 40, the daily limit article works the arithmetic as 10 x 40 = 400 opening emails a day; follow-ups come on top and take priority.

The mailbox limits live in each account's Sending section: a daily limit covering openers and follow-ups, and an hourly limit set by the interval between emails. Mailboxes bought through Woodpecker carry provider caps of 250 a day for Google and Microsoft and 100 for Maildoso and Infraforge, per the sending limits article.

7. Add prospects

The onboarding article lists the sources: Lead Finder, manual entry, a file, your Woodpecker database, an integration or LinkedIn. Before running, make sure every snippet used in the copy is filled for every prospect.

8. Choose the settings that protect the sender

In Settings, pick the sender mailboxes; using more than one is what Woodpecker calls inbox rotation. Then work through the rest of the tab as the editor article lists it: timezone, daily enroll, follow-up, unsubscribe and catch-all options, open tracking, ESP matching and auto-pause for prospects from the same domain.

Two opt-out settings are worth switching on, both described in the GDPR and unsubscribe article. GDPR-compliant unsubscribe lets a prospect opt out or have their data deleted. The list-unsubscribe header adds a one-click option in the mail client. Both work only if the Unsubscribe snippet sits in the email or the signature, and Google's sender guidelines require one-click unsubscribe on marketing messages from anyone sending more than 5,000 messages a day to Gmail.

9. Review and run

Check the Summary tab, then click Run. The onboarding article notes that sending can take a few minutes to start inside the delivery window, and that you can edit the campaign while it runs.

Warnings in Woodpecker's own articles

  • Provider limits still apply. Exceeding them can block the address and return the "You've reached your provider's sending limit" error, per the sending limits article.
  • ESP matching needs OAuth. Mailboxes connected with the Other option are marked Other and cannot be matched; unmatched prospects wait as "Paused (ESP Matching)", according to the ESP matching article.
  • Enroll multiplies. The daily enroll you set applies to every mailbox in the campaign, not to the campaign as a whole.

If you are still deciding between tools, Woodpecker vs Instantly compares the two models.

FAQ

How many emails should each mailbox send?

Woodpecker recommends 25 to 35 a day and advises against exceeding 50, in its daily limit article. The app's ceiling for one account is 5,500 emails in 24 hours, per the sending limits article, which says what the software allows, not what a domain can sustain.

Can a campaign include LinkedIn steps?

Yes, on the multichannel plan, which adds $29 a month per LinkedIn account on the pricing page. The page lists up to 30 connection requests and 250 direct messages a day per account, kept within LinkedIn's limits for the account type.

Why did some prospects get paused?

If ESP matching is on and no connected mailbox matches a prospect's provider, Woodpecker pauses them. Change the sender, or turn matching off, then set them back to Active.

TAGS
WoodpeckerCold EmailEmail Warm-UpCampaign ConditionsB2B Outreach

ABOUT THE AUTHOR

I am Joris van Huët, an enterprise interim CMO. 15+ years, 50+ organizations, including ING, P&G, Nestlé, BNP Paribas, WeTransfer and Vinted. I take on innovation projects (venture building, design sprints), agentic marketing (setting up and running AI agents) and hands-on multi-channel work. See the track record.

I wrote and published this with AI assistance, and I answer for it. Claims about my own experience are limited to the track record above, and a statistic links to its source or is labelled as an example. I sell interim and fractional CMO work, which is why this site exists. How this site is written.

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