The short version: there's no formal "mentorship program" at CSOH and there isn't going to be one. What we have is better - a recurring room full of practitioners at every career stage who already know each other's names, swap LinkedIn URLs in chat, and follow up between sessions. Career-shifting conversations have come out of this. The way to participate is to show up.
The most useful career conversations don't happen in a structured program. They happen in the five minutes after a Friday Zoom when someone says "hey, can I DM you about that?" - how mentorship actually works at CSOH
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What "mentorship" means at CSOH
Most "mentorship programs" pair you with a stranger via a form and a spreadsheet. They work occasionally and fall apart most of the time, because the relationship has no surrounding context.
At CSOH the relationship comes first. Everyone in the room is already there for the same reason - to get better at cloud security. After a few Fridays you recognize names. After a few more you know who works where, who's good at what, and who you'd want to ask a specific question. By the time you DM someone on LinkedIn, you're not a stranger - you're "the person who asked the good IAM Boundary question two weeks ago."
What follows from that is the actual stuff of mentorship: someone reads your resume, someone walks you through the interview loop at their company, someone explains why your career plan is more realistic than you think (or less), someone introduces you to a hiring manager. It just happens without a coordinator and without a label.
Why it works
The mix is the magic
The Friday Zoom regularly has people on their first cloud security job sitting alongside heads of security at well-known companies. The newer folks get perspective they can't get anywhere else; the experienced folks get questions that force them to articulate things they'd stopped articulating.
Repetition builds trust
A one-time speed-mentoring event matches strangers for 20 minutes. A weekly recurring session means you and a potential mentor have been in the same room 30 times before either of you reaches out. That changes the math.
Voluntary on both sides
Nobody is assigned anyone. Mentors mentor because they want to. Mentees ask the people they actually want to learn from. The mismatches that kill formal programs don't happen here.
Right-sized community
Small enough to remember faces, big enough to find a fit. ~2,000 mailing-list members and a few dozen Friday-Zoom regulars - the same names keep coming up, and you can still find someone who's done the exact job you want to do.
How to plug in
In rough order of effort:
Show up to a Friday Zoom
7am PT / 10am ET. Free, no sales pitch. Turn your camera on if you can - it makes a real difference to whether anyone remembers you. Use your real name. Session details →
Drop your LinkedIn in chat
A long-standing CSOH norm - regulars do it, newcomers are encouraged to do it. See the note below on why this is the load-bearing part of how the room works.
Connect with people whose questions resonated
Short note: "Met you in CSOH on Friday - your question about X was useful, would love to stay in touch." The hit rate on these connections is very high.
Join the Signal chat
Most of the between-session conversation - including the "hey can I ask you something about your career?" DMs - starts in the Signal group.
Present
Once you have something worth saying - a project, a lesson, a thing you broke and fixed - offer to present at a Friday. Presenting accelerates everything: name recognition, connections, inbound DMs from people who want to learn from you.
If you want a mentor
A few things that work, gathered from people for whom this has actually worked:
- Be specific about what you want help with. "Will you be my mentor?" is too big a question to say yes to. "I'm three months into a cloud security role at a SaaS company - would you be open to a 30-minute call about how you structured your first 90 days?" gets a yes almost every time.
- Ask people who are 2-5 years ahead of you, not 20. The person who solved your current problem last year remembers it vividly and has the time. The CISO you idolize has 400 inbound asks.
- Reciprocate. Send the person something useful - a paper, an intro, a thoughtful follow-up question. Mentors aren't doing this for money; the currency is them feeling like the conversation was worth their time.
- Be a good Zoom citizen. The fastest way to get someone's attention as a potential mentor is to ask a thoughtful question in session, listen well, and follow up afterward with what you learned from their answer.
- Don't wait until you "deserve" to ask. The community runs on the assumption that people earlier in their career have legitimate questions worth answering. They do.
If you want to mentor
If you've been in cloud security for more than about three years, you almost certainly have something to teach. A few ways to make yourself available without committing to anything heavyweight:
- Stay in chat after the Zoom ends. The most useful five minutes of CSOH every week are the post-call when the structured agenda is over and people ask the things they didn't want to ask in front of the whole group.
- Make your LinkedIn visible. Drop your URL in chat the same way newcomers do. People are more likely to reach out if they can see what you've worked on.
- Reply to the cold DMs. A 10-minute reply to a thoughtful question from a stranger is genuinely high-leverage. You don't need to commit to anything ongoing.
- Present what you've learned. A 20-minute Friday talk on "how we did X" reaches more potential mentees than 1:1 calls ever will, and it pulls the right people toward you afterward.
- Mention you're open to it. Mentees self-select. Saying "happy to chat if anyone's thinking about moving into detection engineering" in chat once a month is enough.
A note on LinkedIn URLs in chat
Sharing your LinkedIn URL in the Friday Zoom chat is one of the longest-running CSOH norms. It looks unremarkable but it's actually the load-bearing part of how this community converts a weekly meeting into a network.
Why we do it:
- The Zoom chat is ephemeral, but LinkedIn connections aren't. Once you're connected, you can still talk in three years.
- LinkedIn shows context - current role, past roles, what you've worked on - that no Zoom intro could.
- It puts the introduction on both people: you're connected before either of you has had to ask the other for anything.
If you've never done it: paste your LinkedIn profile URL into the Zoom chat near the start of the session. That's the whole protocol.
The flip side: the Zoom chat is for community, not recruiting. The norm relies on people not spamming the chat with job posts or sales links. See the etiquette section below and the code of conduct.
Etiquette
- Be specific, be brief, be patient. The people you'd most like to learn from also have day jobs.
- Don't pitch. "Can I get 15 minutes of your time to learn from you?" lands well. "Can I get 15 minutes of your time to show you our product?" does not, and gets you removed from the community.
- Honor the Chatham House feel. Names and stories that come up in conversation stay in conversation, unless the person clearly publishes them.
- Pay it forward when it's your turn. Most CSOH regulars who mentor today were mentored by other CSOH regulars a few years ago. That's how the room sustains itself.
- The full code of conduct applies to all mentorship interactions that touch the community.
Where next
- Friday Zoom sessions - the room where mentorship actually starts.
- Community & Signal chat - the async surface for follow-ups.
- Careers guide - the landscape of roles a mentor can help you navigate.
- Learning Path - the curriculum a mentor might point you at.
- Contribute / present - the fastest way to get inbound DMs of your own.