Effective Cold Email Outreach to CTOs and CISOs in Cybersecurity

Rashi D. · 2025-04-11 12:23:04.164121+00

Hi, I work with a company which is into cybersecurity solutions, we are fairly new ( 5years). I have to start cold email outreach to CTOs & the CISOs. Need suggestions on the content & tone 🧐 Should the email be too technical and tone be casual?

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15 comments

Shlomo F.
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That is an great idea Konstantinos P. thank you for sharing this.
Mike M.
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Konstantinos P. You also could search person on listen notes then look for the podcast on podscribe.
1
Ben B.
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Konstantinos P. this is brilliant, well done.
1
Konstantinos P.
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Hi Rashi D., here’s a 3-step process that’s worked well for me: Step 1: go on ListenNotes.com and search their name. If they come up, it means they’ve appeared on a podcast (there are actually quite a few in that space). Step 2: download the mp3 file of the podcast and transcribe it with Description.com (or I’m sure there’s a free AI solution) Step 3: upload the transcript to ChatGPT, attach the target’s pdf LinkedIn profile, and choose the o3 model (it has reasoning + tools so it’s a step up from the other OpenAI models) and prompt it sth like “My role is X and my objective is Y. I want to break through and connect with person Z (analyze the attached off LinkedIn profile for their position, interests, etc) at a meaningful level. Attached is the transcript of a podcast they appeared on. Can you analyze it and give me an idea of intriguing messaging for: LinkedIn connection request, LinkedIn DM, and email?” From there, you can brainstorm with o3 ideas on how to nurture the relationship, creative ideas to break through, etc. I’ve found it a useful brainstorming partner. It won’t come up with great ideas but it will help you refine yours.
Ben B.
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Rashi D. sure thing, love to hear how it all goes! 💪🏼
Rashi D.
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Thanks Ben B., I will try what you recommended.
Ben B.
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Rashi D. You may never know what will help them most in the moment, given they are constantly iterating but like Pat H. said, research any company you'd be contacting and keep that precise. Show them you did that research. At the same time, blog articles you publish could be about low-level technical updates in their environment. What's the latest with SOC-2 compliance? Are people using their own SIEM/CSM setups anymore, or is AI creating better use cases for security reviews? Provide value to show you're on the inside of the conversation too. Call or Linkedin-message send these blog articles to ask if they ring true.
Pat H.
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I sold the largest deal at my startup (in 2012) by cold calling the CIO of Hearst and having a crisp and well researched value prop, backed my social proof. He would have never emailed me back.
🙌1
🤩1
Rashi D.
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HiPat H. What should be my approach? Would cold calls work better? LinkedIn is not working.
Rashi D.
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HiBen B., can you explain this with an example.
Eia B.
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Rashi D. Try and test what works best - if you’re just starting out, run 2 campaigns of a 5 email sequence each, with an opposite tone. Take it from there and improve! Also, as an ex AE I’m open to giving you feedback on your emails! Send them here: [email protected]
👍🏼1
Ben B.
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They're a hard bunch to reach. I'd also recommend leading with value withe the caveat that you would benefit from their feedback on what could help most right now. Agreed with Ionut-Cosmin L. on the technical newsletter or blog approach being great. Show that your team is leading the way and offer that as conversation.
Neil W.
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I’ve heard the cybersecurity niche is notoriously difficult to crack when it comes to cold email. Maybe skip the technical jargon and lead with value? Also keep it extremely brief — like having a convo with someone at a bar.
Pat H.
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Step one: this persona hates emails
✅2
Ionut-Cosmin L.
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Rashi D. I spent 4 years as a Mkt Ops Mgr targeting CIOs and CTOs and technical content works best after analyst content such as Gartner or Forrester. For ex 'ITIL4 in a nutshell' was top 3 best performing content as lead magnet and the content was highly technical
👍🏼1

Loading comments

Shlomo F.
·
·
That is an great idea Konstantinos P. thank you for sharing this.
Mike M.
·
·
Konstantinos P. You also could search person on listen notes then look for the podcast on podscribe.
1
Ben B.
·
·
Konstantinos P. this is brilliant, well done.
1
Konstantinos P.
·
·
Hi Rashi D., here’s a 3-step process that’s worked well for me: Step 1: go on ListenNotes.com and search their name. If they come up, it means they’ve appeared on a podcast (there are actually quite a few in that space). Step 2: download the mp3 file of the podcast and transcribe it with Description.com (or I’m sure there’s a free AI solution) Step 3: upload the transcript to ChatGPT, attach the target’s pdf LinkedIn profile, and choose the o3 model (it has reasoning + tools so it’s a step up from the other OpenAI models) and prompt it sth like “My role is X and my objective is Y. I want to break through and connect with person Z (analyze the attached off LinkedIn profile for their position, interests, etc) at a meaningful level. Attached is the transcript of a podcast they appeared on. Can you analyze it and give me an idea of intriguing messaging for: LinkedIn connection request, LinkedIn DM, and email?” From there, you can brainstorm with o3 ideas on how to nurture the relationship, creative ideas to break through, etc. I’ve found it a useful brainstorming partner. It won’t come up with great ideas but it will help you refine yours.
Ben B.
·
·
Rashi D. sure thing, love to hear how it all goes! 💪🏼
Rashi D.
·
·
Thanks Ben B., I will try what you recommended.
Ben B.
·
·
Rashi D. You may never know what will help them most in the moment, given they are constantly iterating but like Pat H. said, research any company you'd be contacting and keep that precise. Show them you did that research. At the same time, blog articles you publish could be about low-level technical updates in their environment. What's the latest with SOC-2 compliance? Are people using their own SIEM/CSM setups anymore, or is AI creating better use cases for security reviews? Provide value to show you're on the inside of the conversation too. Call or Linkedin-message send these blog articles to ask if they ring true.
Pat H.
·
·
I sold the largest deal at my startup (in 2012) by cold calling the CIO of Hearst and having a crisp and well researched value prop, backed my social proof. He would have never emailed me back.
🙌1
🤩1
Rashi D.
·
·
HiPat H. What should be my approach? Would cold calls work better? LinkedIn is not working.
Rashi D.
·
·
HiBen B., can you explain this with an example.
Eia B.
·
·
Rashi D. Try and test what works best - if you’re just starting out, run 2 campaigns of a 5 email sequence each, with an opposite tone. Take it from there and improve! Also, as an ex AE I’m open to giving you feedback on your emails! Send them here: [email protected]
👍🏼1
Ben B.
·
·
They're a hard bunch to reach. I'd also recommend leading with value withe the caveat that you would benefit from their feedback on what could help most right now. Agreed with Ionut-Cosmin L. on the technical newsletter or blog approach being great. Show that your team is leading the way and offer that as conversation.
Neil W.
·
·
I’ve heard the cybersecurity niche is notoriously difficult to crack when it comes to cold email. Maybe skip the technical jargon and lead with value? Also keep it extremely brief — like having a convo with someone at a bar.
Pat H.
·
·
Step one: this persona hates emails
✅2
Ionut-Cosmin L.
·
·
Rashi D. I spent 4 years as a Mkt Ops Mgr targeting CIOs and CTOs and technical content works best after analyst content such as Gartner or Forrester. For ex 'ITIL4 in a nutshell' was top 3 best performing content as lead magnet and the content was highly technical
👍🏼1