Ask HN: Resources to get better at outbound sales?

[sieep]

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!

[FloorEgg]

Read "the terrifying art of finding customers" by Collin Stewart

Very few know more about outbound than he does, and that book is recent.

My two cents: It's unlikely you can make outbound work for a custom software dev studio unless you go extremely niche and have a way to target customers with relevant needs. The more broad your services the more new business depends on trust, and outbound has the lowest trust context of all top of funnel sources. What works best for dev shops is word of mouth.

Maybe consider a referral program.

Anything that can greatly boost trust when prospects learn about you.

[anovikov]

Somehow, word of mouth never worked for me. I only ever got one repeat customer (he was really really good first time, but second time, mediocre), and one customer through a referral (very good, but just once). Out of 170+ over 25 years.

I see the reason: my customers are people who don't know anyone they could possibly recommend me to, because they are from random industries and random places. Also their projects are one-off: usually first and last software projects of theirs, ever. Working for someone with large networks who can make referrals means losing money because these people also know good coders and can hire well. I never solved this and rely on outbound all my life.

[jameslk]

Cold sales/outbound sales is dying or mostly dead. SaaS platforms and “growth ops” that made it easy to set up sales sequences and find ICP lists helped kill it. AI making it easy to personalize and do all the work has been the nail in the coffin

This is because sales is a zero sum game. When everyone can do something at scale, like send an email sequence, nobody wins. Now inboxes are flooded with spam that get deleted and phones go straight to voicemail because people have learned it’s not worth it. You can try to create even bigger lists to capture some 0.01% that will respond, but that’s a shrinking game and many B2B companies don’t have the market size for it

Instead, for my company and others I know, we’ve returned to old fashioned human relationships that don’t scale as easily. Building partnerships, asking for warm introductions, conferences, networking, events, hell I even know of someone who knocks on doors for B2B and it works for them. People ignore spam from bots but they’ll listen to real humans. They’ll read emails and take phone calls from people they know. It’s about trust now, not scale

I’d still recommend learning closing and everything needed for once a deal is in your pipeline. I think a book like Founding Sales is good for that, if a bit dated now (skip the stuff about cold sales in the first half of the book). Never Split the Difference for negotiation. For in person sales, this is basically what anyone in partnerships and outer sales do. I don’t know of resources on that. I’m learning from friends who do that and old fashioned searching

[aunty_helen]

Conferences are huge. We’ve done 5 tradeshow demos for our clients in the last 10 months.

I agree with you about the zero sum, once you’ve seen the first hyper personalised email that says they really like your commitment to x, the rest are all the same.

[enraged_camel]

Unfortunately, the reason spam exists is because it works. Same with cold calling.

[groundzeros2015]

When have you bought something?

Example 1: The other day I was trying to fix a sprinkler. My results were mid, then I saw a truck at my neighbors house with a phone number.

1. I was not in the market for sprinkler repair until that day. 2. I was too busy to make a market comparison, seeing that my neighbor did it was enough.

Example 2: I was thinking about refining my mortgage this year. My current servicer called me one day with an offer. It was a competitive but not t optimal deal, but the lady on the phone signaled to me she understood my values and would get it done.

That’s what you are looking for with outbound, people who are in need, willing to part with cash, but probably not shopping for the thing.

This is why cold calling works and why volume is so important. You aren’t trying to persuade people who aren’t interested, but trying to find those who are.

The biggest fear of people with money is not spending money, but that what they pay for won’t work out.

[plasticsoprano]

This is the crux of Michael Dell’s big lesson as a teen that lead to the creation of dell computers. dell had a summer job in high school selling subscriptions to the Houston paper. He realized that the two groups of people most likely to buy were newly weds and those who recently moved. He paid his friends to scour the local marriage certificates and real estate rolls to see who met those qualifications and called only them. He claims to have made more in his summer job than his teachers made all year and paid cash for a new BMW.

[bombcar]

Which means the outbound sales isn’t the first problem - it’s lead generation. How do you find a group that is more willing to purchase given the limited time you can spend on it?

[cj]

There are lots of online resources for outbound sales which will likely be better than advice you’ll find on a forum full of engineers (unless engineers are your target market)

I’d focus on zeroing in on a niche (even if it’s an artificial niche). Develop case studies for how you’ve helped people in your specific niche. Then find people in that niche and offer them those same niche services.

Do not try to be everything to everyone. No one wants to work with a software agency that “does anything”. (Well it’s possible but then you’re competing with thousands of other consultancies).

If you develop into a niche well, you’ll have less competition, you’ll be able to target the right people more easily, and youll be able to write messaging that speaks to people in that niche.

Everything gets easier when you narrow in on a small slice of a market. The problem set becomes smaller and easier to solve.

Once you see some traction, start to expand your niche.

[hansmayer]

> There are lots of online resources for outbound sales which will likely be better than advice you’ll find on a forum full of engineers (unless engineers are your target market)

I mean, the man asked here as a starting point and was probably looking to hear from other engineers who already were in a similar situation. If you don´t have something concrete to offer in way of help, then its better to suppress that urge to sound smart by dropping around general-sounding "pearls of wisdom". You offered a lot of "whats" and very little "hows", which is what I assume the OP was asking for in the first place.

[samsolomon]

Hard question to answer without more details, but I've got a bit of general guidance for B2B sales:

* Know your ideal customer (ICP)—or have a decent idea. Find companies that match that profile.

* Find the right people at those companies. Go on Linkedin and find 3-6 people you think could be decision makers at that company.

* Research those people and figure out how your solution might work for them (RHO).

* Reach out to those people. Communicate what you think their pain point might be and how your solution will help them. Try and get them to agree to a discovery call.

* If they are interested, you'll need to figure out who the decision makers are for buying. If the timing is bad, ask when they renew and reach out again 3-6mos to see how their currents solution is treating them. If they aren't interested, DQ them and move on. Guarding your time here is valuable.

I'm assuming you're a founder or early on. The other comments around MEDDPICC, MEDDICC and other sales methodologies are worth a look, but may be over optimizing if you're still trying to win your first deal.

A bit of background—I was one of the first product designers hired at Salesloft. I've spent a decade building software for sellers.

[1659447091]

Having spent some time in outbound sales (after tech burn-out), the most important aspect (as many comments say) is "relationships". The best training for that is to go out and make them. We had sales training every single day, so it's really not something you can pick up a book or go to a weekend class and walk away being effective. That said, books and classes are a good way to find your footing.

Never Eat Alone - Keith Ferrazzi (networking & relationship building)

Never Sit in the Lobby - Glenn Poulos (sales & relationships)

Getting to Yes - Roger Fisher (negotiation, particularly "principled negotiation")

The Joy of Selling - Steve Chandler

The Psychology of Selling - Brian Tracy

In one of our quarterly division training, our office manager gave us Dale Carnegie How to Win Friends and Influence People and were told if we learned nothing else, to study that book.

It's been over a decade since my sales time, but the 2 sales techniques I haven't forgotten are: "selling ins't telling" and "feel, felt, found". As you can imagine, they are about relating to people, not giving technical/spec speeches.

It's something you have to practice everyday, make sales a part of your job title -- not simply something you do on top of running the company. An integrated layer no different than other software maintenance task, except the maintenance is the relationships with people you want to sell to.

For any other tech types that may someday find they need sales skills, I highly recommend actual job experience in outbound sales (with a company that provides frequent sales training). It was a massive culture shock that gave me the professional people and relationship skills I struggled with.

[warthog]

There was an old legendary HN comment around the following concept:

"All things being equal, people buy from their friends. So just make more friends"

If you are confident of your services, just make more friends. Talk to people more. If it is too salesly already, you lost the conversation. Instead try and learn about their lives. I sometimes even open up with "No agenda to sell, genuinely curious"

Note: If anyone finds the link to the comment, please drop it here to credit the author.

[mekoka]

Could it be https://news.ycombinator.com/item?id=23285438

[gus_massa]

I found too many sources in Google, one from 1997, but I can't find the origin of it.

[nateb2022]

Probably Colin Dowling:

> I say in every talk I give: “All things being equal, people buy from their friends. So make everything else equal, then go make a lot of friends.”

[jppope]

Thats old as time. The more basic form of it is: "Don't worry about selling, just make a friend"

[Eridrus]

I generally recommend the book Founding Sales (available for free online), but it's targeted at SaaS founders.

But you're actually doing something even more common: running a consulting business, and there's plenty of content on that for just that reason, so I would go find content on how to scale a consulting business, e.g. this seems like the start of a thread to pull on https://training.kalzumeus.com/newsletters/archive/consultin...

[wj]

I wanted to say your insight about a consulting business is spot on.

I also recommend Founding Sales and think it would be worth the OP skimming.

Also, search for Steli Efti (founder of a CRM called Close) who has some great content for outbound sales. I thought he did a session for Y Combinator's Startup School but didn't just find it. But he has lots of great content and a bit of a hustle mentality.

[gist]

Your website (luniv.tech) is (for lack of a better way to put it) 'all over the place'. You are (from what I can tell) a 1 person operation. Nothing wrong with that. But you should try to focus on at most 3 things that you can do well and cut your site down to talking about those 3 things. Then (despite what everyone here seems to be telling you) you should cold outreach to people who can use those items and learn from the failure (and rejection). If you keep at it you will get results (and you will learn).

Also register and use lunivtech.com as your website (it's open now). Don't use .tech as your primary domain.

[h317]

It is way easier to fix a specific problem than to find one and sell solution for it.

For example, Hi I’m John and my accounting software can increase your profits by 10% by reducing time spent doing billing.

Vs

Hi I’m John, we do custom software and we can do an app for you in accounting for example, but also a crypto wallet or a booking website.

If you are in the second route, there is no mass outreach strategy because you are not offering anything specific your customer is anyone and your solution is anything. The outreach works for the first category, because spam or not, if someone is offering to fix a problem I have I’m ready to listen. Hence the relationship advice, if you provide services, people around you need to know that you “do apps and stuff”, and if you do products you can throw 1,000 emails fixing one thing with some level of certainty that someone within the ICP will give you a chance.

[eddywebs]

I can attest as someone who has been pitched former(and sold), is better than latter.

[mmarian]

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]

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]

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]

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]

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.

[dwa3592]

- 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]

Some good comments in this old post.

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

[fallinditch]

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]

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]

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.