Decision-Maker Outreach

A practical system for finding the exact people who can say "yes" and reaching them in a way that feels natural rather than salesy.

The core idea: you don't find decision-makers by searching harder, you find them by understanding their world well enough that it becomes obvious where they are. What does their day look like? Where do they spend free time? Which conferences, chats and communities do they actually value — and which are full of vendors pitching each other? Once you know that, the "where" and "how" mostly answer themselves.

B2B vs B2C framing

Figure out which situation the user is in first, because it changes who "the right person" is:

• B2B — the decision-maker is the customer. Reaching them converts directly into revenue.
• B2C — the end user is a consumer, so the decision-makers worth finding are at partners: companies that already own the audience you need. The value exchange can be technical integrations, media/co-marketing, expertise swaps, introductions, or anything that creates value for both sides. Start by listing which big players already have your audience, what they need, and how that can be turned into money for both of you.

The workflow

Walk the user through these five stages. If they're already partway in (e.g. they have a crisp ICP), skip ahead — but check the earlier stage is genuinely solid, since weak ICPs are the most common reason outreach fails.

1. Define exactly who you need

"Business founders" or "marketing people" is not an ICP. Push for specifics:

• Role — the title of the person who feels the pain and who controls or strongly influences budget. Note if these are different people.
• Company — industry, size (users, revenue, headcount), stage, geography.
• Trigger moment — the event that makes them need this now. This matters most: timing is what closes deals. A great product pitched at the wrong moment is ignored.
• Pain + current workaround — what's broken and what they do today instead.
• Budget reality — is there money for this, and whose line item is it?

Help the user write a one-paragraph ICP. Example of the target level of specificity:

CMO at an iGaming company with ~100k–200k users. They used to buy traffic profitably via Meta, but since Meta rolled out AI optimization their ad accounts get banned too fast and unit economics broke. Our product adds a layer that lets them acquire users at roughly their old cost. The CMO owns the acquisition budget and is under pressure to restore growth this quarter.

If the user's ICP is vague, ask pointed questions rather than accepting it. A test: could two different people read the ICP and independently pick out the same 20 companies? If not, it's not specific enough.

2. Customer development (talk to ~10 of them)

Before hunting at scale, get conversations with a handful of people who fit the ICP. Don't sell — the goal is to validate assumptions and collect information Google can't give you.

Questions worth asking (adapt to context; see references/playbook-assets.md for a fuller bank):

• How do you solve this today? What have you already tried?
• Who do you trust for advice on this? Whose opinion changes your mind?
• Where do you get information — newsletters, podcasts, chats, people?
• Which events or communities are actually worth your time? Which are a waste?
• What do you do outside work — sports, clubs, hobbies you share with peers?

After a few conversations, the same names, places and communities start repeating. Those repeats are your entry points. Help the user log answers so the pattern is visible (a simple table: person / tools tried / trusted sources / valued events / communities / hobbies).

Warn about the conference trap: events that promise "hundreds of CMOs" are often full of people like the user — vendors trying to sell. The gems are usually smaller and less advertised: a Saturday padel tournament that senior investment bankers play near Central Park, a private dinner series, an invite-only chat. Customer development is how you hear about these.

To get the first 10 conversations when you have no network: ask for advice (not a meeting), lean on second-degree intros, offer something useful in return, and ask every interviewee "who else should I talk to?"

3. Pick a natural entry point

For each promising place (offline or online), work out how the user can legitimately be there. Options include:

• Sponsor or co-host (a small sponsorship of a niche event often buys more access than a booth at a big one)
• Participate genuinely — play in the tournament, join the community as a real member
• Go with someone who already attends, as their guest or teammate
• Contribute — speak, run a workshop, organize a side event

The only requirement is that the user's presence feels natural and doesn't raise questions. Keep it honest: showing up as yourself with a real reason to be there is what makes the later relationship work. Don't advise inventing a job title or background to get in — if it's discovered, it destroys exactly the trust the whole approach depends on.

4. Build the relationship, let them connect the dots

Big B2B deals are a long game built on trust. Coach the user to:

• Make a good impression as a person first. No pitching on first contact.
• Wait for the natural question — business people will eventually ask "so what do you do?"
• Answer briefly, then mention one recent, concrete case where they did something impressive for a company just like the listener's.
• Stop there. Let the other person connect the dots and ask the follow-up. A pull feels completely different from a push.

Help the user prepare that one-sentence "what I do" plus the case story in advance (see templates in the reference file).

5. Growth hacks to accelerate

Suggest the ones that fit the user's situation:

• Find the niche online gathering spots. Telegram/Slack/Discord groups, forums, subreddits, private communities — sometimes hundreds of target people in one place. Ask about these during customer development; members will name them. Join as a contributing member and follow each community's rules on promotion.
• Lower the barrier to talking to you. It's hard to build a relationship when the first interaction is a sales pitch. Give value first: invite them onto a podcast, feature them in a newsletter or report, start a community for people like them, host a dinner. Once a relationship exists, the sale is much easier. Podcasts and "expert roundups" are especially effective because being asked for your opinion is flattering and low-commitment.
• Dig into niche or dead social networks. Startups sometimes built a network for one specific audience and managed to attract lots of your target people. Active or not, the public profiles there reveal who's in the space; if it's still active, reach out right there.
• Reach people where they're actually responsive. Many decision-makers ignore LinkedIn inboxes but answer on other channels. If someone publicly lists a Telegram, X or other handle on their profile, site or talk slides, that's a fair channel. Because the channel is more personal, the bar for the message is higher: short, specific, clearly relevant to them, easy to decline.
• Write good cold messages. Whatever the channel, the message decides the outcome. See references/playbook-assets.md for structure and examples.

Guardrails

This playbook works because it's built on trust, so keep the tactics on the right side of the line:

• Use contact details people have made available, not ones pieced together against their wishes. Don't recommend tools or workflows that de-anonymize people, scrape private groups, or map someone's email → hidden accounts → private chats they're in. Beyond ethics, it's the fastest way to get labeled creepy in a small industry where everyone talks.
• Respect privacy and anti-spam law. In the EU/UK (GDPR, ePrivacy), cold B2B email to individuals needs a legitimate-interest basis, relevance to their role, clear sender identity, and an easy opt-out; many countries restrict unsolicited messages. Mention this when the user is planning volume outreach, and suggest they check local rules.
• Follow platform rules. Mass DMs, automated scraping and bots in communities get accounts banned and burn the entry point for good.
• One follow-up, then stop. A polite nudge is fine; repeated chasing on personal channels is not.

If the user asks for something past these lines, say briefly why it backfires and offer the closest effective alternative (e.g. warm intros via a mutual, value-first content, or joining the community properly).

Output format

When the user asks for a plan, produce a Reach Plan with these sections (skip ones that don't apply, and keep each tight and specific to their case):

1. ICP — the one-paragraph profile, plus trigger moment and budget owner
2. Hypotheses to validate — the 3–5 assumptions custdev should confirm or kill
3. Customer development script — 8–12 questions tailored to their ICP, plus how to land the first 10 calls
4. Entry-point candidates — a table: place / online or offline / why target people are there / how to get in naturally / confidence (guess vs. validated)
5. Relationship plan — the "what I do" line and the case story to drop in
6. Growth hacks — only the ones relevant to them, made concrete
7. First messages — 1–3 draft outreach messages for their top channels
8. Next 2 weeks — a short, dated action list

For narrower requests (just a cold message, just an ICP, just a list of communities), answer only that piece — don't force the full plan.

When the user's industry is specific, use web search (if available) to find real communities, events, newsletters and podcasts for that audience, and label anything unverified as a hypothesis to confirm in customer development.