What lands in a CTO or IT director's inbox
There are 670,570 computer and information systems managers in the United States, according to the Bureau of Labor Statistics Occupational Employment and Wage Statistics for May 2025. Median annual pay is $175,140, or $84.20 an hour, which puts fifteen minutes of their time at about $21.05. That number explains most of what happens to your message: a CTO or IT director is not being rude when they skip it. They are protecting an hour that is already spoken for.
What actually arrives: vendor sequences, recruiter templates, internal escalations, a security questionnaire, and a note from someone who wants fifteen minutes to show a platform. Most of it is about the sender's product. Very little of it is about the systems the recipient runs.
So the messages that get read share a shape. The first line is about their environment, not yours. The ask fits in one sentence. The time it takes is named. They read in a fixed order: who is this, is it about my environment, what do they want, how long will it take. Fail any one of those and the message gets archived, which is worse than deleted because it never comes back.
Before you write
Pick the question first. A good one has a fork in it: did you keep the in-house queue or move to a managed service, did the migration finish before the reorg. Those are answerable in two lines from a phone. A bad one is broad enough to require a meeting, something like what is your cloud strategy. If you cannot state your question in one sentence, it is not ready.
Then do twenty minutes of reading. Job postings are the most honest public document a technology team produces: they name the stack, the scale, and the team you would sit beside. Engineering blogs, public documentation, and conference talks fill in the rest. You need one specific detail, not a dossier, and you should never imply you know more about their setup than you do.
Decide how much of their time you are asking for before you write a word. A quick question is five minutes. A considered reply is fifteen. A review or a short call is thirty. An hour of advice is an hour. Naming the size is the difference between a message that can be answered on a phone and one that gets postponed indefinitely.
Choose the channel after that, not before. Email works when the address is published and you have something specific to say. LinkedIn works for a shorter version of the same message, especially with someone who posts about their work. A paid message is for the case where you have no route in and you want the seriousness of the request visible before they spend the time.
What to say in the first message
Boomerang's analysis of more than 40 million emails found that messages of 50 to 125 words got the most replies, that one to three direct questions did better than none, and that plain writing beat formal, college-level prose. All three findings point the same way: write the way you would to a colleague at another company.
The weak version asks for a tour: "I wanted to see if you had thirty minutes to walk me through your cloud strategy and how you make vendor decisions." That is a meeting request dressed as a question. The stronger version gives them a fork: "Your posting for a platform engineer lists Kafka and Terraform. Did you keep the on-prem brokers or move them?" Two lines to answer, and it proves you read something they published.
Keep the subject under 70 characters and make it about their world. "Kafka migration question, [Company]" beats "Quick question" because the second one could be from anyone about anything. The subject's only job is to survive the scan.
One clear ask, the time it takes, and the reason it is them in particular. Then say what happens if they do not answer: a two-line reply is plenty, and you will send what you learned either way. Mean it. A message that gives the recipient an easy exit gets read more often than one that traps them.
How to follow up
Wait about a week. Then send one follow-up that adds something: a result, a number, a shorter version of the ask. "Same question, shorter: did the migration land before the reorg?" is a legitimate follow-up because it saves the recipient work. "Just checking in" is not, because it asks them to reread the thread and find the ask again.
Change the size of the ask if the first one was too big. If you asked for thirty minutes, drop to a single question they can answer in a sentence. The goal of a follow-up is to make replying easier than ignoring you, not to remind them that you exist.
Two follow-ups is the limit. Space them a week or two apart, then stop. If the issue is still live in six months, write a new message about the new situation rather than reviving the old thread with three paragraphs of context.
If email stays quiet and you have a shorter version with the same single question, LinkedIn is a reasonable next step. Sending the same paragraph on three channels in three days is not persistence; it is noise, and it reads that way.
When a paid message makes sense
On Introworth, members set a price for messages from people they do not know. Your card is held, not charged, and payment is captured only if the recipient replies within the reply window; if they do not reply, the hold is released. The recipient keeps 85% of the price, and prices start at $15.
The pricing comes from the pay data rather than from haggling. Fifteen minutes at the national median of $175,140 is about $21.05, which is why $25 is the suggested price for a considered reply. A five-minute question maps to a suggested $15. Thirty minutes, about $42.10 of their time, maps to $50. An hour, $84.20, maps to $100.
In the highest-paying markets those same minutes cost more. Median pay is $291,660 in San Jose, $232,890 in San Francisco, $215,300 in New York, $214,960 in Boston, and $214,680 in Seattle. If you are writing to someone in one of those cities, a $15 request reads differently than it does elsewhere.
Use a paid message when you have no warm route and your question is worth real money to you. Before you pay, Introworth's message coach checks the draft privately for length, questions, the reason it is them, the time you are asking for, and plain wording. Two cheaper options exist first: connections message each other with no per-message fee, and a member can ask a mutual connection to introduce them, with the connection forwarding a note or declining and the person accepting as a free conversation or passing. Try those before you spend.
Pay figures come from the U.S. Bureau of Labor Statistics and are computed by Introworth's price calculator. The guide text is drafted with AI from those figures and Introworth's product rules, and checked automatically before it is published. It is general guidance, not legal, tax or financial advice.