absolute-dotfiles/.config/omo/skills/cold-email/references/outbound-plays.md

Outbound Plays

A play is a repeatable outbound motion: a trigger, an offer, a sequence, and a definition of success. Plays keep outbound from becoming a pile of one-off emails. This reference covers four that work in 2026, with the conditions each needs.

1. Value-first teardown (services and agencies)

Give a specific piece of the work before asking for anything. It works best when what you sell is expertise someone can see: conversion optimization, design, SEO, ads, copy, analytics.

Trigger: something visible changed or matters right now: a new pricing or landing page, a redesign, launched ad campaigns, a new head of growth, fresh funding with growth targets.

The sequence

1. Email 1 asks permission, with no link. Name one specific thing you noticed on their page, and offer the rest.

   Looked at your new pricing page. The annual toggle defaults to monthly, which usually costs a few points of annual uptake. I noted two other things I'd test there. Want me to send them over?

2. When they say yes, send a 2–4 minute video (or a one-page annotated screenshot) covering 3 specific, testable ideas on their page. Show their page on screen in the first seconds.
3. Follow-up asks a small question about the ideas, not for a meeting: "Was the second one already on your list?"
4. Then offer the call: "Happy to walk through how we'd prioritize the rest."

Why the permission step: no link or attachment in the first email protects deliverability, a "yes" filters for real interest, and the teardown goes only to people who asked for it. That keeps a time-intensive asset efficient.

Rules

• The ideas must be real and specific to their page. A generic checklist dressed as a teardown burns trust and the brand.
• Give enough to be useful, and leave the "how we'd do all of it" for the call.
• Volume is low by design: around 50 well-chosen accounts a week, mostly Tier 1 and 2.
• An agent can draft the teardown (screenshot, analysis against your CRO or design framework), but a human expert reviews every one before it goes out. It represents your expertise.

Measure: permission rate (yes to email 1), teardown-to-call rate, call-to-proposal rate.

2. Product-led outbound (self-serve and freemium SaaS)

Reach out to people already using the product, when their usage shows they're ready for more.

Triggers, in rough order of strength:

• Hitting a plan, credit, or usage limit
• A large job or upload (a much bigger list, project, or import than usual)
• Inviting teammates
• Signing up from a company domain that matches the ICP
• Returning repeatedly to pricing or upgrade pages

The sequence

1. Within minutes of the trigger, a short plain-text email from a founder or named account owner, sent from their own address. Reference what they're doing:

   Saw you're verifying larger lists this week. If you're running these before outbound campaigns, a couple of settings help with catch-all domains. Happy to share them, or set you up with a volume plan if you're doing this regularly.

2. LinkedIn connect the same or next day, for company-domain users.
3. One follow-up with a specific resource for their use case.
4. Stop if they upgrade, go quiet for two weeks, or say no.

Rules

• Speed matters more here than anywhere: the trigger loses most of its value within a day.
• Never make the tracking feel like surveillance. Talk about the job they're doing and leave the logged events out of it.
• Offer help first and an upgrade second. Product-qualified users convert far better than cold contacts (vendors report many times higher), so you don't need a hard sell.
• Route accounts that exceed self-serve limits to a person. See the revops skill's routing rules.

Measure: trigger-to-reply rate, trigger-to-upgrade rate within 14 days, expansion revenue per triggered account.

3. Problem-led cold outbound (any product)

The default play for accounts with no product usage: lead with a problem the segment is known to have, prove you understand it, and offer something small.

Trigger: a signal from the prospecting skill's signal plays reference, or a tightly defined segment.

Offer something smaller than a meeting: a sample of the work (verify a sample of their list, audit one page, benchmark one metric), a relevant resource, or a quick answer to a question they're probably asking.

Example for a technical product (an email verification tool selling to agencies that send cold email for clients):

Agencies running outbound for several clients usually find out about a bad list when the domain is already hurting. Want me to run a sample of one client's list through and send back what would have bounced?

Rules

• The problem must be specific to the segment, with proof from a similar customer.
• The free sample has to be genuinely small to deliver, or the play won't scale.
• If you sell deliverability, compliance, or quality, your own outbound has to be flawless. A bounce, a typo, or a missing opt-out from a company selling those things undercuts the pitch.

4. Founder-led outbound

Early-stage, or for a small set of strategic accounts: the founder writes personally, from their own account, about why they built the thing.

• Short, personal, specific to the recipient. No templates.
• Ask for advice or feedback as often as for a meeting. People answer founders.
• 10–20 a week, done consistently, beats occasional bursts.
• Pairs naturally with the founder posting on LinkedIn, so the name is familiar when the email lands.

Choosing plays

If you...	Start with
Sell services where expertise is visible	Value-first teardown
Have self-serve users	Product-led outbound for usage triggers, plus problem-led for everyone else
Sell a technical product to a defined segment	Problem-led with a free sample
Are pre-product-market fit or chasing a few big logos	Founder-led

Run one play at a time until it works. Each needs its own copy, its own success metric, and a few hundred touches before you can judge it.