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Posted by sieep 12/21/2025

Ask HN: Resources to get better at outbound sales?

Hi!

I run a small custom software company in Michigan.

I want to get better at outbound sales beyond just cold emailing or messaging people through LinkedIn.

We’re about to start publishing case studies and doing some outreach, so I want to take some time to study outbound sales and improve my skills.

Any recommended courses, books, or frameworks for B2B outbound sales, consultative selling, or building effective outreach pipelines?

Thanks!

240 points | 68 commentspage 2
mmarian 12/24/2025|
Figure out who your target customer is. Imagine yourself in their shoes - how/where do you spend your time, what do you like learning about, under what circumstances would you consider a rando small software company in Michigan.
raverbashing 12/27/2025||
1 - Understand the main processes that sales orgs use (MEDDIC or its variations) - you don't need to follow it in all its details but yes in the general idea

2 - Understand what is the problem you're solving and how companies can benefit from it

3 - Understand how companies actually do procurement

4 - Outbound sales are the ones that sucks the most. A rejection is just a rejection, don't take it personally (one part of having actual sales people is being a more impersonal process - they care about the sales but a rejection is taken less personally)

adeptima 12/28/2025||
Real tip - find someone who loves outbound, can create a funnel outside of Linkedin or convert traffic from Linkedin to something more reliable and can talk about numbers non-stop for hours.

Ex. I never did more than 1k whatsapp messages with 20% open rate in a month ...

Know a friend who is doing 190k MRR with 12k whatsapp messages open rate 40%-60% (no AI SDRs!, fake avatars, etc) and what to double it next year. All he wants to talk is outbound ... and how it will make rich and how it should cost no more than 20% revenue.

99,999% hates outbound with passion, want to dump on someone else, can't retain SDRs for more than 6 months, etc

jppope 12/28/2025||
I spent the first chunk of my career doing sales (2nd half spent in software engineering). Theres a lot of good books out there but you're going to find a lot of the direct advice to be non-applicable (as I'm sure you can pick up from the comments). Most of the Literature out there is directed at professional sales people, who for the most part are non-technical, have the backing of a marketing org, and are also different than a founder. Anyway, heres a reading list. Most of the trainings I've been a part of were custom built to the org or market, and frankly I learned more from Rules of the Game by Neil Strauss. I did enjoy "the Wedge" training by Randy Schwantz... that one you should do the video not the book. It also sounds like you could use some marketing stuff so I'll throw some of that in there too.

In no particular order, and please keep in mind this is off the top of my head:

* Influence (the classic)

* YC videos (e.g. https://youtu.be/0fKYVl12VTA?si=I9uylXSRyOf1nXRv, https://youtu.be/DH7REvnQ1y4?si=Ke858PmaaBr5ar-e, https://youtu.be/hyYCn_kAngI?si=sO_co6kbDaNn3cql, etc)

* Thinking Fast and Slow

* Purple Cow

* Clayton Christensen stuff

* Spin Selling

* Challenger Sale

* Guerrilla marketing (for the mental muscle)

* Jeffrey Gitomer (basic but useful)

* Lean Startup (for positioning)

* Charisma Myth

* Minimalist Entrepreneur (bits and pieces)

* The presentation secrets of steve jobs (just a good book on presentations, framed around Steve Jobs to sell more)

For what its worth this question comes up fairly often. It seems like technical people would like a "technical people" guide on how to do Sales and marketing. Does that sound useful to anyone?

dv35z 12/28/2025|
Sales & Marketing guide / playbook for Technical People would be great. I am a solution/sales engineer and would find a ton of value in that.
jppope 12/28/2025||
okie dokie. I'll work on it.
dwa3592 12/27/2025||
- Go hangout where your potential buyers hangout. It could be LI, IG, TikTok, Golf clubs, High end bars, Charity events. Make those connections.

- Make two (nested) lists - the people you know in real life- and the people they might know. Now, can any of these people be your potential buyers? if they are in first list, good, just talk to them, if they are in second list, ask for an introduction from your connection in first list.

- Advertise where your potential buyers might notice.

tiffanyh 12/28/2025||
Some good comments in this old post.

https://news.ycombinator.com/item?id=43823851

fallinditch 12/28/2025||
Search for 'vibe marketing' on YouTube. Please note: I am not necessarily recommending this, but it is instructive to understand how some of your competitors could be leveraging technology in this way. Some of the techniques may be effective for you on their own, for example automating part of your keyword research activities.
brudgers 12/21/2025||
Relationships are the best resource for sales.

Because to solve someone's problems, they have to tell you their problems.

Or to put it another way, the thing you do is to solve the actual problems other people have. That's what you need to sell. You aren't selling the fact that you know how to use a hammer. You are selling the idea that you can build the right hammer for the job.

So sales is not "out reach." It is "what do you need?" and you will probably do better by optimizing for getting to that conversation, not through optimizing for low effort on your part.

Linked-in is best used for networking not push notification. Networking is about trust. Maybe you can't help with someone's problem but you know someone who can.

Finally, you can't sell desperately. Good luck.

hamiecod 12/28/2025|
As a newbie in the world of entrepreneurship, I tried outbound sales for 3 months with my first venture. Was never worth the effort. In my opinion, it is extremely difficult to sell to people who aren't looking for the stuff or are interested in the stuff you are selling.
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