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Today, I turned 50 years old. When I came out of my house this morning, my trees were toilet papered, and signs about my 50th birthday were put up in my yard. My wife (who is older than me) reminded me that I am now an old man. My phone and LinkedIn have been blowing up with "Happy Birthday" messages. Here are a few observations from a
I received two types of birthday wishes today:
- Genuine, thoughtful, and personal messages
- Automated thoughtless messages
My family and friends invested time and thought into sending me genuine, thoughtful messages and actions (yes, even the "decorations" in my yard, which I have to remove from my trees later today). I very much appreciate these. However, the automated thoughtless messages that are so easy to send these days are automation at its worst. Let me expand on that thought.
I love and appreciate the value of efficiencies that AI and automation can provide us as much as the next tech head. But when they promote laziness and impersonal automated interactions, they seem not helpful but rather annoying.
I recently encountered something similar in my business. I was setting up a business profile on a new platform (which will remain nameless). I connected it to my LinkedIn business profile, and there was an automated process that would ask me a series of questions and tailor my business listing based on the answers I provided. One of the questions was, "Is your business growing?" I answered "yes". Apparently, based on that and no further approval or interaction from me, it automatically wrote job descriptions for 3 jobs. It posted them on my new profile and one on my LinkedIn business page. It didn't even notify me that it had done this. The job posting(s) were challenging to find within my business listing. It wasn't until about 24 hours later, when I started getting a few genuine, thoughtful, personal messages on LinkedIn from a few candidates, that I could do some digging and find that my business had become a victim of automation at its worst.
It turns out that the "bot" that was obviously powered by AI and automation posted this job on LinkedIn with the "EasyApply" option, which allows candidates to apply from their mobile app with just a few clicks. In 24 hours, about 300 candidates applied. Of those 300, only 3 messaged me directly, which is only 1%! These are the few I connected with and will be on a short list of people I will turn to in the future should I have an actual job opening.
Due to the way that the automated bot posted the job, I didn't have direct access to reach out to those that applied and let them know what had happened. However, through manually cross-referencing on a few data points I was able to deduce who most of the applicants where. From there, it was a manual process for me to send them each a message. Here is what that message looked like:
I need to come clean - A fractional CTO job posting was accidentally created by new AI platform connected to my LinkedIn profile and I believe you applied. As someone who's been a fractional CTO and SaaS CEO for over 25 years, I felt terrible about unintentionally leading you on.
To make this right I wanted to give back and fully reimburse the time you spent applying to the job.
I just recorded an unfiltered, raw, and value-packed video for serious fractional CTOs who want to acquire 3-5 more clients by Q2 2025.
Inside, you’ll see the exact tech stack, marketing tools, and offers that helped me close clients easily as a fractional CTO, including:
- The three critical pillars every successful fractional CTO must master (beyond just technical expertise)
- Common pitfalls that keep talented technical leaders from landing high-value clients
- My proven framework for positioning yourself as a premium fractional CTO
Watch the free training here: [[link to video]]
Looking forward to your success as a fractional CTO!
P.S. The free video will only be available for the next 3 days before getting paywalled in an exclusive community for high growth CTOs. Don't miss out!
Best,
Drew Harris
Former SaaS CEO & Fractional CTO/CPO
Yes, I recorded a video I thought would help them and shared it with them. The process of "fixing" this issue I had encountered through automation at its worst took me about 8 hours.
Why did I invest that time? My reputation and interactions with people are important to me, and I value genuine personal messages. The response from the candidates to my message was mixed, to say the least. About 25 people watched the video, 3 or 4 people were pretty nasty, and about 10 people replied and said thank you.
I share these stories with the same hope and motivation that drives most of my work these days: to help people and develop genuine, thoughtful interactions as I grow and invest in those relationships. I would love to hear your thoughts and feedback in the comments!
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