Ask HN: How to learn to sell?

Hi there - one of the few pro sellers on HN here.

You're planning on prospecting into one of the most rejection-heavy domains out there with small physical business. These people get dozens of calls per day from companies they've never heard of - many of whom are trying to rip them off - and even the best ones (Groupon, Yelp, google ads, etc.) are basically just rent-seeking. Oh, and most have gatekeepers who don't care the slightest bit about your pitch.

Because of that I'd stay away from all this "smile and dial" advice. You'll have no chance. Go out there and hit the pavement and meet these people at their establishments at off hours. If you catch the owner in there at a good time - do your best to inform them of your products benefits and come up with a really good offer to get started (something that loses you money and time). Free Trial, free month of services, whatever makes sense based on the context of your business. The goal is NOT to make money or build a book of business at this point - it's to get a person happy with your software to sell to later.

If the owner is too busy or whatever - have some stuff printed out for them to read later that you can drop off. Ideally with a small gift (coffee, food, candy, etc.) and come back in a few weeks to see if you catch them at a better time (again with a gift, until they talk).

A solid entry level book would be Fanatical Prospecting by Jeb Blount.

Good Luck.

*edit to fix book name

Was coming here to reply: Fanatical Prospecting - start there. Glad it is in the top comment mentions.

Good book to get a solid base on all the sales jargon and learning the generic sales cycle that applies to all products and services and businesses. It’s legit The Bible for all AEs/BDRs, I’ve even heard hiring managers / HR people say to potential candidates to read that book before applying for a sales role as the X Sales Manager / VP really applies the philosophy in their team(s).

There's a reason that people still employ door to door salesmen: most people don't like to reject people in person. It's why you normally buy your new roof from a guy you just met and have so much trouble firing employees who used to be good but have fallen off the wagon.

My partner worked as a waitress and had to kick out sales people all the time. It's amazing how many people want to sell stuff to restaurants and show up to "talk to the boss". Of course the boss had work to do and didn't want to see any salespeople...

Yeah "talk to the boss" is how spam worked before email

Thanks but no thanks

I would recommend a slight verbiage change from "owners" to "decision makers" - depending on the industry and such, of course. I often end up gatekeeping on behalf of the owners of the business(es) I work for because they are far too busy/uninterested in random people trying to sell (legitimately useful) products and services, simply because the owners aren't necessarily the ones who would be the best point of contact for demos and the like.

If you're trying to sell us a new software platform, you want to talk to our IT and Finance decision makers. If you're trying to sell us magazine/trade journal subscriptions, you want to talk to our Supply Chain/Marketing/Safety decision makers. If you're trying to sell us a physical product you'll want to talk to our Procurement/Operations/Production decision makers. And so on.

The owners of any given business might need to be involved later on, but they are rarely the best people to talk to up front if you're trying to sell something.

Fanatical Prospecting

Should be the book name (I just tried to find it)

I briefly worked at a company that sold to restaurants. Just to emphasize this: they are hammered by people dialing for dollars. So OP is competing with SDR teams running sequences through outreach.io or similar.

Realistically, OP has to develop a different sales channel. Which is both intimidating and probably more intimidating than it needs to be, because OP (likely?) isn't trying to be a billion dollar business, so doesn't need enormous scale.

One (obvious?) suggestion to investigate is conventions or the local chamber of commerce.

Selling to small businesses can take almost as much effort as selling to mid-sized or enterprise companies and your price point will be much smaller. It also takes about as much effort (or more) to support small businesses. I sold ecommerce software to small business for more than a decade and in retrospect, I should have charged 10x the price and sold to the bigger customers. Automation and scale will be your friend if you're selling to smaller businesses. You may need in-person sales at first to get feedback from your customers and make sure what you've built has product-market fit. Once you're reasonably sure you have a market that gets value from buying your software, think about automating as much of the sales funnel as possible. Buy email and mailing lists. Google Ads. Social Media ads. Whatever can scale and work 24/7 for you because your time is finite. A/B test your sales pitches and narrow down language that resonates with your customers.

Most important advice (and you can see it repeated here) is that you need to be used to rejection. An average developer might get never get a PR fully rejected -- a well oiled sales team expects to close only 1/3rd of their sales qualified leads. If you're starting from cold calls, you will be lucky to close <1% of your outreach, prepare for that mentally.

But also (again repeated in other comments) you aren't selling a tool, you're looking for their problems, try to understand them in their words and then show how giving you money makes them go away (it doesn't have to all be solved with software, your skills in setting up the system can be just as valuable).

Happy to talk more if you aren't comfortable discussing in a public forum: [email protected] (we make software to make remote SaaS demos better: https://www.demogorilla.com)

I had sales training in a "seven dwarves" computer company. I quickly learned that sales wasn't for me, and switched to sales support; but I then spent a good eight years working alongside very experienced salesmen (all very unlike me, but I liked most of them a lot).

It's said salesmen are always selling themselves; I don't agree. But they're always pretty engaging company.

They taught us that a good salesman can sell anything. But that's hyperbolic; you have to know the product you're selling inside out.

They taught us to sell solutions, not features. That means (as someone said upthread) you're looking for people with problems, and you need to find out what their problems are, so you can help them.

We used to get leads by setting up stalls at exhibitions. I guess your prospects aren't the exhibition-going sort? But they probably gather somewhere; maybe you could go there.

I dropped out of sales because I couldn't cope with the dubious ethics. Not my employer, particularly; but there was an awful ot of politics, we were taught how to commit expenses fraud by our own boss, and everyone was fiddling commission. It wouldn't surprise me at all if brown envelopes exchanged hands.

There's a difference between marketing and sales. You're building a solution to a problem. Marketing is about getting people who have the problem to know your solution exists. Sales is about convincing them to pay money to solve the problem.

If you built the MVP but don't have customers yet, you should already have some people in mind who suffer from the problem your solution is supposed to solve. Selling is then just a conversation that loosely follows the following steps:

  (a) Ask if they still have the problem
  (b) Ask if your proposed solution solves their problem
  (c) Ask them to spend money to buy your solution

Note that every step starts with "ask". This means that you need to listen to their response. If they don't still have the problem, walk away. If your proposed solution doesn't solve their problem, listen to why not, and focus on improving your product until it does solve their problem (hopefully in a generic way such that your improvements will help you sell to other customers in the future). If they aren't willing to spend the price you're asking to buy a solution that they consider to be a solution to a problem they have, then find a way to add more value so that they will be willing to pay that price.

There are a lot of misconceptions about sales, especially from people that don't sell. A lot of that is because Hollywood and TV enjoy presenting people as shyster salespeople.

Essentially, the first thing to remember is that you're there to help them make money. Believe that, and your job is easier. Think of yourself as someone who just found this great service and they should use it because it'll make their lives easier/better/etc.

But first, you have to find your customers. Who are they? Where are they? How do you get to them?

That's what this book is for:

https://smile.amazon.com/Traction-Startup-Achieve-Explosive-...

Then how do you talk to them? Why should they trust you? This is one book that might help with that:

https://smile.amazon.com/Soft-Selling-Hard-World-Persuasion/...

Small businesses are hard to reach and hard to sell to. But if you get enough of them they become an impenetrable moat that will allow you to get revenue forever.

As other people have said, you may have done stuff in the wrong order. But there are plenty of startups that have done "if you build it they will come." It just costs more. I mean, you need to sell something!

You obviously built it with a customer's needs in mind. Who was that customer? A friend? Your business? That should be part of your marketing story.

Good luck!

To be frank you've already committed the classic blunder of developer initiated startups. You built before you sold. Now there's no telling if what you built is what anyone wants.

IMHO, and extrapolating a lot here it's very unlikely you will get any sale based off your MVP. It's unlikely that you've hit the right market fit without first having found customer #1.

So I'd back up a step and find someone with the problem you're trying to solve. Offer the deal of a custom built solution to meet their need. Once that's built and validated that it actually solves the problem then start selling to others.

It's not a blunder 100% of the time. Sometimes non tech people need to see it working before they understand.

Assuming the founder knows the problem non tech people have, which in practice doesn't happen except in very very very rare cases.

^ This. Exactly this.

By committing to building BEFORE you know what to build, you may have invested a lot of time to just get "NO". Stop what you're doing right now and go and talk to 20 people who might be customers and DO NOT PITCH them. Find out their problems and explore from there.

> DO NOT PITCH them.

+1. Try to pitch me and I will use every skill i know to get away. DO NOT PITCH before you are 100% sure you know me.

It's not entirely a blunder but OP should consider the MVP as almost a straw man. Don't be precious about how you've designed it and don't be shocked when customers say this is not at all what they need. Having a prototype could still be invaluable for eliciting feedback.

First impression: this is the reverse order, because you started selling the moment you chose to invest in this business idea.

You already know the value, otherwise you would not have made it. But more so, you ought to have audience already engaged before you write the first line of code, if it is a code-oriented value proposition for your brand.

Getting market share, building traction, cultivating momentum, these are all totally separate of having the product actually online. The key is the value proposition. And if you cannot get attention for that, without the product even there perhaps, you have no "yellow brick road" to travel, and sales do not make themselves. But if you get attention for something, all you have to do then is follow through on the promise of your brand, and deliver the value.

Cold sales work great when your value proposition is natural, and market is not cluttered. But I would refer you to "The Lean Brand" for the real mindset you need, no matter how you sell:

http://leanbrandbook.com/

My 2 cents... you need to start doing cold sales and it'll be very difficult as you'll get flat-out rejected 95/100 times.

Learning about sales will feel more productive and in your comfort zone but you should start by going out there and talking to customers. Get out of your comfort zone.

I'd start by going door-to-door so you can start gathering feedback from SMBs and get a sense of the true ICP. Once you've closed ~10 clients this way then you should consider using a sales engagement platform like Outreach, Hubspot or Salesloft which will automate the cold email to call. If it's a 1-call close type sale, then you can use something like https://www.mojosells.com/. You can buy lists from Zoominfo or otherwise.

That all said, any type of human-centered sales motion in North America will require a minimum annual contract value of $10,000/yr to scale up.

I'd recommend "To Sell is Human" by Daniel Pink: https://www.amazon.com/Sell-Human-Surprising-Moving-Others-e...

I'm a product-focused founder. I read this a few years ago when starting out with selling my company's product, and it helped me reframe sales as something essential to most of our jobs in the knowledge economy.

There's a compelling argument that persuasion and storytelling are core human activities, rather than the domain of extroverted "salespeople". Adopting that mental model was just as useful for me as learning the tactics of how to be effective at sales.

* > I believe the key to success here will be "Cold Sales" *

100% correct.

1. Get a demo ready that you can show on a laptop. Focus on features.

2. Smile and dial. Set a meeting with the business owner or manager to show the demo.

3. Listen. The things they say (mostly objections) will guide your product development.

4. Accept rejection. You will get meetings from 10% of your calls. You will make sales on 2% of your meetings if the customer even needs the product.

Reading is a good way to forestall the heartache of actual sales, but that's it. Everything you need to know you'll learn in meetings.

I would put Listen on top of the list before anything in sales. The colder the sales get, the harder it gets and the better you need to listen. Give your product away, for free to each and every SME you know. Demo it, let them use it, and get many, many feedback rounds.

Also, look at other angles to approaching market segments. Door to door sales in non primary products just isn’t feasible at scale. The conversion rate is too small. Remember that many SME pretty much shit on their software, but they got it via their IT-support, or bookkeeper/ accountant or professional association. Those are angles to sell that could get you a better effort to conversion ratio.

Don’t just accept rejection, but learn to thrive on it. That is the secret of sales.

How do you thrive on rejection? Genuinely want to learn.

General steps -

1. First, disassociate. Most of the time, rejection is about the subject (doing the rejection) being closed to something new rather than some notion of the object (of the rejection) being undesirable.

2. Gain confidence in the object. Understand that the object has its own merits. The object isn't undesirable, rather, you're looking for subjects who appreciate what the object has to offer. That a given subject doesn't appreciate the object, has no bearing on the object. Move on and find other potential subjects.

3. As potential subjects polarize and reject the object for reasons that are to be expected - because the object is what it is, and does not attempt to be what is not - recognize rejection as an affirmation of the object's qualities.

Most of the loop between (2) and (3) is about improving the clarity of communication, such that subjects do not make mistaken rejections, either because (a) the values of the object are not clear to the subjects or (b) the unsuitability of the subject is not clear to the object.

Depending on how the rejection was given, you can use it to recalibrate your methods or presentation. Avoid "sour grapes" mentality.

So I faced/facing the same issue.

In general before you do any sale you need leads. I.e. you problem is not selling, but prospecting. I.e. you need prospects at the top of the funnel.

There is very good book - "fanatical prospecting" :

https://www.amazon.com/s?k=fanatical+prospecting

So your first step is to raise awareness of your product.

To do that there are two way - inbound (blogs,etc) and outbound(cold call / cold email). For inbound, you need to provide value to customers which are not related to your product. I.e. first earn trust and give value.

For outbound, the key is lead filtering, I.e. looks for signals that would qualify your leads (e.g. sector, traffic). But in general outbound is a numbers game.

Remember that you want to sell your product, but your clients just want to resolve the problems they have.

So don't look at it as selling - reframe it internally as wanting to find businesses where you can genuinely help them and resolve some of their issues, and then work with the business to solve the problem they have.

fwiw, during my tech support days, I "sold" more by never trying to sell anything because I had no interest in it. What I was interested in was problems, and seeing me solving their problems with the different tools our company had made a ton of sales apparently.

So agree with the above; don't try to convince them they want your product, figure out their issues and exactly how your product solves those issues

This is a very subtle but great point to start off.

"How can I sell my software?"

"How can I help these folks out?"

I actually just saved a tweet this weekend that lays it out really simply: https://twitter.com/janvmusscher/status/1581254065274892289?...

“Huge clarity if you structure your sales call like this:

> Uncover where they are now (A)

> Uncover where they want to go (B)

> Uncover what's stopping them (C)

Then pitch your offer as the solution to C”

From what I've read:

If you haven't got C, either build the missing parts (assuming that the customer is the right one) [0], or find another customer [1].

If you realise they don't really need B that much, then no amount of sales is going to help you [2]. Time to pivot based on A or find a new B?

[0] Chasm crossing - A Pennarun, https://archive.is/cHeKx

[1] Users you don't want - M Seibel, https://archive.is/tCCLa

[2] Making something people want - T Blomfield, https://archive.is/8IDcl

Go to places where those business owners hang out, and simply get to know them. Try your local Chamber of Commerce for a start. Local CPAs will know a lot of local business owners, and would be another good place to start. One way to get to know a CPA is to hire one to do your business taxes. Then take him to lunch, and talk about your business, and ask for his help.

Sales is three things:

  - Sourcing. Figuring out where your customers' hangout so you can reach them there.
  - Prospecting. Reaching out to your potential customer base.
  - Closing. Going through with a deal including sales collateral, proposals, and contracts.

The entire process should be a system that is tweaked as you execute it. Great books I’ve read are:

  - Ultimate Sales Machine
  - Sales EQ
  - Fanatical prospecting
  - Challenger sale. For the actual closing process
  - The Close.com blog is pretty great.

I highly recommend the Dale Carnegie Sales course which is once a week for IIRC six or eight weeks.

When I took it long ago the class included me (enterprise SW sales for my startup), a woman selling chip fab equipment for KLA-Tencor (24-36 month sales cycle with ASP above $100MM), a woman selling ADT home alarm systems, and two guys who had opened a T-shirt stand on the beach (sales cycle <10 min with ASP of $20). We all got the same lesson and all learned a lot from each other. A very hands on class and you bring to each class how you used the lessons during the preceding week. One of the best investments I ever made.

The stages a customer goes through (whether over 5 minutes or 25 months) are “attention, interest, conviction, desire and close”. The first time I met one of the best sales guys I have ever known, when he changed PowerPoints during a presentation displayed this desktop, and his wallpaper was just those words. Even at his high level he lived them.

No more books, no more blog posts and nothing teaches as you speak to a few customers first.

Go and meet 20 customers and learn what they do and how you can solve them.

Then come back and read whatever you want to read now and it will everything makes sense.

I can recommend “How To Sell Anything” by Harry Browne. Corny title, and the content is from the 1960s. But it’s the best no-B.S. explanation of selling I’ve seen for a nerd/thinking/introvert type of person.

You need to deeply understand who your potential clients are.

By that I mean where they "hangout". How you can reach them.

How? Talk to them. Build relationships. Maybe online if there are specialized forums, or maybe at the bar, or maybe by first visiting them physically. Not with an hidden agenda but with the sincere goal of helping them to solve their problems. Then you will see if your product is a great solution to their problems and if it can leads to a business relationship or if you need to iterate on your MVP.

Selling a new product is all about doing things that don't scale in order to get as much sincere feedback as possible.

Finally learn to not take rejection personally but as feedback.

Good luck. Small businesses run on tight margins and there's already a massive amount of people trying to extract more out of them.

I'm willing to bet you don't add any value whatsoever to their business (tech people typically don't "get" small business with physical stores) and I don't think sales techniques will help you do anything except maybe convince unsophisticated business owners...

As someone who's run a few restaurants before, if you don't have my cell number, you're not talking to me period.

What is more valuable to you right now? Sales, or feedback that will help you improve your product and its positioning?

Don't let anything (e.g. lack of the right approach) keep you from listening to people.

Only after you've spoken with 10-20 people will the advice in sales books (Founding Sales, SPIN Selling etc.) be valuable.

If, after hearing what those 10-20 people have to say, you've decided to focus on changing your product instead of selling what you have, you might try to implement the steps in "The Mom Test".

Disclaimer: random advice on the internet. Take it with a pinch of salt!

How do you know they'd want it if you haven't already be talking to them face to face? A friend and I used to do this when we were getting started in web design. We thought "surely all these restaurants and cafes would want better websites to attract more customers". Turns out actually nobody cares, they don't even care about serving quality food or coffee a lot of the time, many don't even see the value proposition of having a bike rack. The owners are often lazy entitled assholes even if they're not responding to a cold call, unless they're immigrants. The only successes were face to face, when you're already a customer or regular patron, and they do express they actually need something done. Square is the most successful startup I'm aware of with small businesses like this.

They may not necessarily be lazy OR entitled.

Every business has it's laundry list of problems. Every business.

Your list of problems and worldview may differ a great from their day-to-day reality. Very few want to work on resource suck that has a unknown outcome. Your selling a SaaS service to them (just picking the example in this thread as the example) isn't likely their biggest problem or decision at that moment.

I've tried and failed at this, a SAAS that served small builders.

Your best bet is probably the blog and going to conferences. However I only got one customer that way.

It's also worth looking at partners. Do these companies have software that they're already using and could those partners upsell them onto your software?

I hired a cold calling firm. They made a lot of calls, but didn't get any free signups to the product, or any demos.

Done three years of stock broker. Basically it's about making friends and helping each other. Absolutely hated the gig but that was the way to do it.

I’m no entrepreneur but from the media I’ve seen around recently (podcasts, articles, think pieces) you should be selling before you code, that is, eliciting problems from clients.

Intuitively it seems harder to sell a piece of software which exists concretely, than to sell a solution/maintenance to a problem which can evolve constantly. Would you rather buy a shoe that may or may not fit, or retain a shoe maker to build a custom shoe for you?

If you want to sell an existing piece of software though, I’d probably do it through an App Store and focus efforts on optimizing it’s visibility there. That way you can leverage the existing ecosystem (and let them take a cut) instead of sinking time/money into creating your own.

No substitute to getting out and actually doing the sell but this book will get you tons of ammunition to make your offer bullet proof. Don't go by the title. It has very actionable advise:

$100M Offers: How To Make Offers So Good People Feel Stupid Saying No

https://www.amazon.com/100M-Offers-People-Stupid-Saying-eboo...

I learned to sell… by selling.

I read how to win friends and influence people and made up prompts based on that knowledge. Went out there and sucked hard for two months. And then it clicked and my business took off.

How? Sell!

Jokes apart: selling, like many other things, is mostly about a lot of practice. Some theory might help, but in the end, you will learn only by doing lots of mistakes.

I suggest you try to create a safe, friendly opportunity to sell something, and exercise (e.g. try to sell biscuits to your neighbors)

Very good question.

I’ve been programming for just about 30 years in one shape or another and the 2 skills I wish I had learned from an early age are sales and copywriting.

What I can say (as an amateur of both disciplines now) is that yes, find the books and courses etc.

But, the most important thing is to start selling and writing right now.

It’s the absolute best way to learn. The books and courses will accelerate your practical efforts.

Don’t wait.

Some ideas:

Take a look at how Grub Hub and similar services reached out to get restaurants to sign up for their service.

Read the book Influence: Science and Practice by Cialdini

Get some type of CRM system in place so you can keep track of who you talked to and who you need to follow up with. It doesn't have to be fancy--even note cards will work, but just come up with a way to manage that information.

I'd be remiss if I didn't mention this movie:

https://www.rottentomatoes.com/m/glengarry_glen_ross

Get ready to work 100 times harder than you think you need to, to land that first big client. But it can be done. It's how it's always been done.

I was not very successful myself, but just pick up the phone and talk with them would be already a big step.

After the first couple of calls you stop being afraid of it and it just go much smoother. But following up and make sure everything is aligned takes much more time that I expected.

Often it is not a yes or no answer straight away, but it is more a chasing, communicate, listen, learn, plan, follow up, etc...

But again maybe I was doing something wrong myself.

Here is a good book that was suggested to me; and I have suggested to quite a few founders. I found some topics to be dated but the overall content is simple to digest and easy to follow.

Also, Marketing and Sales are two different beast.

Founding Sales, https://www.foundingsales.com by Pete Kazanjy (I think he is here on HN too.)

More of a passive idea, but you could add potential customers on linkedin and wait until they mention anything related to what you do, then reach out via linkedin. Less pushy (you will need to still be doing the pushy kind of sales), more thoughtful, and has worked for a number of sales people I know in different industries.

Read patio11's writings on the subject of small software businesses, if you haven't already.

https://www.kalzumeus.com/

My wife had a startup which didn't get traction, because she didn't like selling. Then she learned selling, grew her startup and sold it successfully to a competitor.

The book "How I Raised Myself From Failure to Success in Selling" got her started.

Random advice, perhaps, but purchase Book Yourself Solid by Michael Port and do the work therein (there's a workbook and such). It will help with the cold sales as well.

Since we’re here on HN,

Did YC alum learn any sales skills from the accelerator program? If so, was it direct or indirect ?

I would actually say that you have gone about the process in the wrong order. That is to say, you should start off by talking to your clients /first/. Figure out what their problems are. Collect all of that.

Then, come up with a concept tailored directly to their problems. You probably need no more than a 1-3 slide deck to show this to them and figure out whether the concept is desired by your end customer.

Finally, and only once you've validated that the concept is desired by your end customer, you build the product.

The problem with doing it in the order you've mentioned, is what happens when you go and show your product to a customer and they say "Nope, I don't actually have an issue which your product solves. Thanks but no thanks."

Sales is the beginning, middle and end of your journey as a founder. Building the product only comes in over time once you've found something worth selling.

There are multiple ways to approach this but here's the core you should integrate: sales is a quantitative discipline. Be quantitative about it.

This means building a sales pipeline and tracking the effectiveness of whatever channels you use. How many leads do you get for $X in ad spend? How many of those become customers? What (ultimately) is the value of those customers?

Whatever you read, you will have to try different things. Some of them work. Many will not. Get in the mindset that you will fail more than you will succeed and don't just assume that you will get organic sales with sufficient reach. Sales is an active discipline. You will need to go out of your way to make potential customers aware of you and you will have to work to find a problem of theirs you can solve.

Be prepared to make a financial case for why they should buy from you vs [alternatives].