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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 4
wek 12/27/2025|
I'd recommend learning from Jason Lemkin at SAAStr and from Jen Abel. She did two great podcasts with Lenny on Lenny's Podcasts.
dnsb 12/28/2025||
6Sense has some great output: https://6sense.com/science-of-b2b/buyer-experience-report-20... and https://www.demandgenreport.com/blog/6sense-research-84-of-b....

the tldr: Raise your visibility. It doesn't mean becoming an influencer but focusing on what is relevant to your customers. We all hate LinkedIn, but it is where a lot of our customers spend time, so meet them there. Post articles, comment, show that you're knowledgeable and not a bot.

I'm launching a new website (helping to detect fake AI candidates for recruiters) and you'd think the ICP would be pretty straightforward....it's not. Knowing your ICP also requires you to know the pain they're experiencing in their company and within the market at the same time as the pain they're experiencing personally. It is not easy at all.

Cold outreach is hard, but if you can get the person, the company, the market pain points and the outreach right at the right time, it can be a gold mine. I've been using my friend's website https://salesbrief.co (you can sign up for free and test it) as it helps with this. It's showing some promise for me and might help you too

whynotmaybe 12/27/2025||
This book has some often overlooked insights :

Traction: How Any Startup Can Achieve Explosive Customer Growth

ISBN 0241242533

arathis 12/28/2025||
Hey, I ran a custom dev agency for a decade. Happy to answer questions
hasperdi 12/28/2025|
Not OP, but I do have a question. How did you do lead generation? What works?
andrewstuart 12/28/2025||
Depend on it to pay your bills or starve.

Make about 1,000 calls.

franze 12/28/2025||
Book: Never split the difference. By Chris Voss
firefax 12/27/2025||
So please trust me I'm not just ask me to be a reply guy. but... what do you mean by "better at outbound sales"?

Like, you want to call up a company and get them to buy your software? To pay you to make them software?

Because while either way I'd say be more targeted -- try to network IRL and have linkedin (retching noise) just the place you go to get their email... and then make a targeted pitch to a smaller number of people you've met IRL. Budget to go to a few conferences.

But that's a strategy I think works best if you have good product and want to get businesses to pay to use it, and is less effective in selling "consulting" (sarcastic finger quotes).

Either way though, going to conferences where people will be legitimately interested in your product (Think going to HOPE instead of Blackhat)... offer to take people out to dinner, expense it as marketing.

Also I don't reccomend buying people alcohol, just food. For whatever reason, people will overdrink and turn into asshole reasons when alcohol is free... by all means point them to a decent dive bar.

(For example there's one behind Bally's that's attached to a convenience store. They used to let folks buy shit in the store and eat it in the bar if they weren't entitled about it.)

If you're selling that you can make cool stuff, software wise? Try more academic conferences. A lot of people would kill for a decent software engineer, it can be extremely hit or miss with academic CS types, they often would love people who can do stuff like set up a limesurvey server or whip up a nice looking static site for their lab or do really basic stuff like make R scripts to automate stuff done in the opendocument equivalent of excel...

But no course, book, or framework for outbound sales will ever Trump face to face interaction. A lot of companies discount who being the "cool guy at the conference" can lead to sales... especially as people age (because again, I said go for authentic gatherings, not sport coat fests).

Over time, if you combine being friendly with having something of value, sales will happen -- those in person leads will be your most valuable IMHO.

SMAAART 12/21/2025||
Google these:

1) "inbound marketing"

2) The lean startup / MVP

HPsquared 12/27/2025||
I'd watch Glengarry Glen Ross.
AznHisoka 12/23/2025|
Hot take, but outbound selling is so ineffective today, that if its it in a playbook, it most likely means it doesnt work
philangist 12/27/2025|
So what would you say should be in the effective playbook for selling going into 2025?

Also running a small consultancy firm like OP and coming from a technical background, building an effective sales motion is the hardest challenge.

AznHisoka 12/28/2025||
If its in a playbook, its already ineffective. Use your own creativity to do something that isnt scalable or in any best how-to guides or books is a good start
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