How to break into tech sales in 2025

This started as a LinkedIn post, but then I crossed the 3,000 character limit and moved it here. If you’re new here, welcome to Fatherpreneur! This newsletter is usually about how to write newsletters, but today it’s about how to break into tech sales in 2025.

P.S. I recently started a podcast with Troy Munson called Two Dads in Tech, and we have high hopes and dreams for it in 2025. Every Wednesday we talk about things people in tech think about, but don’t necessarily want to talk about (or maybe don’t have anyone to talk to about). It’s a phenomenal podcast and a labor of love. It would mean the world to me if you went and subscribed 🙏 

Okay enough about that, let’s get into it.

If you're trying to break into tech sales for the first time in 2025, this is exactly what you should do:

1. Make a very simple website (I would use beehiiv because it takes less than 30 minutes to throw something together, and is going to make a lot of my other suggestions 10x easier to implement). Make a post or page called "About Me". This is your opportunity to illustrate who you are with 100% of your personality. Do not hold back, do not copy-paste from a Chatbot. Be yourself.

Go deep into what makes you tick, why you're specifically unique in your approach to building relationships and grabbing attention (both important in sales), expound on details, and describe what transferrable skills you have that make your break into tech sales particularly sensible.

Make sure the post is configured with a "pop-up" to subscribe. This takes 2 seconds to do on beehiiv, and gives people the option of following you there as well as LinkedIn.

Add this website URL to your bi-line on LinkedIn so every time you post anything on LinkedIn that button to view your site is right there beside you.

2. Connect that subscribe form to a welcome email. Again, here you should be yourself, thank the subscriber for following your journey, give a personal peek into why you're doing all of this, and ask them to tell you why they subscribed. Engage with every single reply. This is your community, and it matters, and it will help you get a job. You might find others who are in the same boat as you, and you might even find people who can help you get the role you’re looking for!

3. Make a post on LinkedIn about who you are, what you've done, why you want to break into tech sales, and a specific CTA to follow you on your journey. This is a condensed version of what you already did in step 1. I talk to people allllll the time who cannot get past how uncomfortable this first social post is.

GET OVER IT.

Do you want to be comfortable or do you want to get a job?

Write the post and ship it.

4. Make a dream 100 list of companies that you want to work at. Spend quality time building this list. The list can be 10 or 20, but if you spend a solid amount of time building 100 accounts, you will be grateful you did. Mark which ones are actively hiring and which ones aren’t. You don’t necessarily need to wait until one is hiring to land the job. The next steps are going to show you how to get the job even if they’re not hiring, but obviously if they’re hiring that’s good to know. If you have an enrichment tool like Apollo or LISN you can add some contact info for a few people at this point too, but we’ll get to that a little later.

5. GET COMFORTABLE ON CAMERA. Go yell at a mirror or something. Idc what you need to do, but this part is THE WAY you are going to set yourself apart from the millions of other people trying to do what you're doing. 99% of them will not do this part, and 99% of them will not get the job they want.

6. With the list you built in step 4, prioritize from most to least desirable companies, and do 30 minutes of research on each. You don't have to do all of this at once, one at a time is fine. 

7. Once you have 30 minutes of research on the first company, come up with a sales pitch. Decide 1) who you're selling to and 2) what part of the product you're selling. Then film yourself for 60 seconds pitching the product. If you're already good at creating TikToks then you can go pretty deep with this where you talk to yourself — one of you is selling and the other is buying. The more creative you are the more noticed you will be. Start every single video with the same exact words to build your brand and become familiar. Example: “I’m leaving my job as a teacher and breaking into tech sales.” This one liner should be super concise. It’s important that you say exactly the same thing at the very beginning of the video every time you start. In every video, assume no one knows who you are. This is your chance for a one-liner introduction, and algorithms love it.

8. Post that video on LinkedIn and tag the company. Say "If I were on the sales team at {company}, this is how I’d pitch their product on a cold call.” You can focus on a more broad sales approach but I think a cold call is probably best because you’re most likely going to be an entry level SDR if you’re never been a tech seller. Video is absolutely 100% going to accelerate your search. Do not focus exclusively on written word. Do both. I can’t stress this enough.

9. Reread step 8 100 more times.

10. Post the video you created on TikTok, not just LinkedIn. If you don’t have an account start one and post it. Caption something like “breaking into tech sales in public by selling {company/product}.

11. Then make a post on your newsletter with ~100 words of writing for context, embed the TikTok you just created, and ship it on both email + blog (1 click with beehiiv). Make the title super easy to understand (also helps with SEO over time). Something like “Selling {tech product} in 60 seconds".”

Here’s an example of how it is to embed a video on a beehiiv post. The below took me 1 second to embed.

@twodadsintech

If you’re not buying a ton of the same thing, are you even a dad? #sales #dad

12. DM the LinkedIn post to 3-5 people at the company you’re “selling” in the video. Pick 1-2 individual sellers (these will be your champion when an opportunity opens up) and 2-3 sales leaders (sales manager, director, VP). Some of them will have DMs open on LinkedIn, so you can just message them. Others might have DMs closed, so you can request to connect and include a personalized note, something like “just made this video selling your product! thought you’d appreciate it”. Apparently LinkedIn just throttled personalized notes to 5 per month for free accounts, so if you have the budget I recommend paying for the cheapest version of LinkedIn Sales Nav, but if you don’t have the budget you’ll just have to be creative. Sales Nav will also give you a lot more insight into who at each company you should reach out to in the first place. Tools like Apollo or LinkedIn Sales Nav can help you find the right contacts at the company you’re building for, but even without those, this free approach will get you traction.

13. Turn on notifications for the people at that company you just DMd so that every time they post you react and add value in the comments. You’re not pitching yourself here, you’re become a familiar face. This is key. You being familiar will strengthen this connection-to-be.

14. If the company you just posted about has an open role you want, go apply, and in the cover letter explain what you’re doing, drop the link of the video you just made selling their product + the link to your website where you posted about their product. You want to really flex here about why you are the only logical choice for this position. Lean into your ambition, why you’re hungry, why you’re capable, all your transferrable skills, etc.

15. Mention to the people you DMd the video that you applied to the role, and express your interest. If one of them already replied on the early message, lean into that relationship and build the connection. You want someone to champion your candidacy internally and at least flag that you did all the work outside of the scope of the application that really proves you are legit and not just another job application. Some companies get thousands of applications for a single role. What you’re doing is setting yourself apart from thousands of people.

16. Repeat step 7 through 15 with all 100 of the companies you wrote on your list, one by one.

17. BONUS. Make a list of 100 people who are doing exactly what you want to do in their current roles. Turn on LinkedIn notifications for them and engage with everything they say, add value in their comments. This is an extension of your community. You’ll learn so much by doing this and being a sponge, and you’ll build a really strong network of people who are all doing what you want to be doing.

This is simple, but far from easy. The entire loop I’m suggesting above might take 7-14 days for each company (or even months, it really depends on which company you’re going after), but you can do more than one company at a time.

I suggest doing 3-5 videos per week at least.

There will be a balance of just the right amount vs. too much. But in reality the longtail length of time for breaking into conversations with each of your companies will vary, so juggling multiple companies at the same time will increase your chances of landing quality conversations with the right people.

If you do this methodically you will get a job faster than everyone who doesn’t do this, and you will likely break into a role at a company much better than if you just spray and pray resumes into every company chaotically and without much thought.

Hopefully this helps someone!