Ask HN: How to learn sales?

865 points by northpoleescape ↗ HN
First time entrepreneur here. I am creating a product that will solve address a large potential. The more I think about it and read about startup, I am finding that a key to early and often success is Sales.

I am been engineer by choice and engineering manager by profession. I have never done sales. I understand you learn by doing similar to driving. I am a bit talkative but sometime I have hard time not getting bogged down by emotions.

How do I get started? Can you share books, videos, tutorials, prior recorded sales call references?

Where can I learn about metrics to track? Any ideas?

242 comments

[ 0.26 ms ] story [ 1940 ms ] thread
Crossing the Chasm, The Little Red Book of Sales, To Sell Is Human, and The Challenger Sale are great intros to sales, especially for those coming from a technical background.

I like HubSpot for tracking / metrics. They have an always free tier too.

It shills a little hard for Salesforce IIRC but "Predictable Revenue" was very helpful for me.

"Never Split the Difference" is good even if it leans a little hard on a single rhetorical device, and it offers really easy to practice stuff in an ontology that makes sense to engineering brain for every day life.

"Barbarians at the Gate" is borderline academic but unbeatable for understanding how all deals, no matter how big, are shaped by personalities and emotions. Huge huge time investment but worth it if you have serious entrepreneurial ambition.

Way of the Wolfe by Jordan Belfort. Bar none best pure sales book out there. It really did make a big improvement on my sames abilities. And yes, the guy is scummy, but damn his book works.
I am exactly in your shoes. Doing marketing as I write this.
How I raised myself from failure to success in selling - Frank Bettger. It's a classic.

I think sales can be broken down into:

1. Foundation of being perceived as an authority

2. Lead generation

3. Persuasion and conversion

4. Re-sale

Breaking it down makes it easy to become better at the sales process.

+1 for the book recommendation. Probably the simplest book ever written on sales.
Here's how. Hit the street and try to sell something to passers by. Hot day - maybe coupons for ice cream. Rainy day - maybe some umbrellas at a major bus stop or transit station. Keep leveling up from there. Find a problem and sell folks the solution.

All the book recommendations in the thread are solid.

The best thing I ever learned in sales is people must be comfortable to be successful. Find something relatable and that will often lead to comfort which will lead to a productive conversation/chance at a sale.
I think the book "Spin Selling" may be worth your time.
- Sales and Marketing go together, but the paths diverge once you know the importance of each function. It is good to get a broad idea of both. You can do some courses on coursera/MooCs, and try to get hands-on with running some marketing campaigns. - "The Challenger Sale" is a fairly easy and good book to read in general. - Have a look at SaaStr channel, there are some nuggets there https://www.youtube.com/c/Saastr/videos

All the best. Try out a lot with short feedback loops so that you can course correct suitably. Always respect the customer and their needs.

Something important to know is the difference between an actual sale (i.e. closing) and a sales process. If you want to be a good sales person, you focus on the sale, but if you are building a company, you need to figure out a sales process (which usually includes marketing on one end and onboarding on the other, not just sales).

It doesn't matter how good of a sales person you are if you are not getting any leads. Conversely, you can be a bad sales person, even with a bad product, but with enough leads, eventually they will buy - you can see this with crappy restaurants at airports for example.

Successful startups are very aware of this and they setup processes to generate enough leads so their sales people can close them, to generate their target revenue. Also, the sales person's responsibility is to close the people that "come through the door", but it shouldn't be their responsibility to bring those people in.

The Sales Acceleration Formula by Hubspot Sales leader Mark Roberge is a good book for this. He was an engineer by training.
This is important and is largely what I wanted to add. At my company we have sales, who do the traditional listening to understand customer needs and working with them to build a deal that addresses those needs. But then we also have demand generation / sales development, focused on cold calling, getting leads, other marketing, etc, to get people through the door and you say. The OP needs to consider which of these (could be both) they want to build up their skills in. Reading about how to do sales will not help if you dont know how to get in front of people in the first place.
This process is very nicely defined in Predictable Revenue by Aaron Ross & Marylou Tyler.
As a new salesman, your main issue is getting over rejection. If you don't learn how to do this properly, you'll end up not explaining your product properly, hesitating to present to marginal prospects, and changing your product too readily from criticism.

So just go about doing the usual sales thing of describing your product, finding prospects, and talking to them. A lot. I think density of rejection is actually key to thickening your skin.

You need to separate sales from marketing. Sales is a conversation, marketing is a broadcast. Marketing gets the phone to ring, sales takes the call and closes the deal.

For B2B sales resembles project management: the goal is not to convince everyone to buy your product or service but to diagnose their needs and only engage with firms that will benefit.

For larger deals you "sell with your ears" as much as you talk.

I find Neil Rackham's "Spin Selling" very useful. Peter Cohan's "Great Demo" embeds a lot of discovery advice and suggests that a good demo is really a conversation driven by mutual curiosity about customer needs and software capabilities.

For B2B customer development interviews (those early market discovery conversations) I have a short book you may find helpful. See https://www.skmurphy.com/blog/2020/01/30/40-tips-for-b2b-cus... (there is also a link at the bottom for a PDF version).

Two final books I would suggest, while not exactly sales books, are "The Innovator's DNA" by Clayton Christensen and "The Right It (Pretotype It)" by Alberto Savoia. They cover a number of techniques for finding the right problem to solve and determining if your solution is a good fit for customer needs. I mention them because it's not uncommon for a startup to have a product problem that manifests as a sales problem.

I’m not in sales at all, but learning SPIN works great to make a case for something in a structured way. It’s like a funnel to bring people into agreement with my viewpoint.
Sales is also graded by level of "touch". For example, selling IT services contracts is very high touch. Signing a deal could involve weeks of written correspondence (RFI, RFP), in-person pitching, contract negotiation, etc. Low touch could be fully automated with simple, non-negotiable pricing. There are lots of levels in between.
Weeks. I wish.

:-)

My first job ever I befriended one of the senior sales guys at an after work drinking event. We built software that integrated into and with a range of embedded devices of which many were medical. He was one of the guys that worked closely with our EMEA customers who were notoriously slow to sign.

Three years later he drove in to the office lot with a brand new Porsche 911 which was a portion of his commission for closing the deal after something insane like 33 months.

He was happy to have that deal done.

I’m two years into brokering a deal between a client and two blue-chip behemoths. It has been endless cycles of documentation, specification, certification, auditing, horse-trading, rescoping, consulting, wargaming, ratifying, and many of the faces have changed over the last two years.

It’ll be a big deal for all of them, but just getting everything in place for them to all agree and sign is just insane - my longest sales process before this was maybe 4 months, 400 hours - this has easily eaten tens of thousands of man hours so far.

One thing I’ve observed is that the deal almost becomes secondary - by this point, there’s an entire self-sustaining bureaucracy around the deal, many of the deliverables the deal specified are already in place and money has changed hands, hires have been made, everything has essentially happened as though the deal has gone ahead - yet I’m spending this afternoon rejigging information security roles and responsibilities to make the interfaces more on parity with the security team of one of the blue chips, because until the contract is signed, the deal isn’t done, and all parties are just merrily swimming out into deeper waters together, growing technical and operational dependencies around each other with no legal agreement. At this point, the businesses are just getting on with stuff as though the deal is done, the counsels are screaming because nobody is interested in moving the boring paperwork forwards, and I’m charging by the hour. Buys a lot of popcorn.

Sales is weird.

Edit: just realised we might be talking about the same healthcare customers.

(comment deleted)
> You need to separate sales from marketing. Sales is a conversation, marketing is a broadcast.

Close, but not quite.

Marketing is the brand, the image, points of differentiation, etc. It's the message.

Advertising is the broadcast. It's how the message is communicated. It's the medium.

Marketing + advertising = prospects and leads.

Sales is the last mile. It takes the results of marketing + advertising (i.e., leads and prospects) and guides those to closing.

Contrary to myth, successful sales is about listening, not talking.

Sales is

That definition is very—let’s say—unique. In my 7+ years of marketing I have never met anyone or read anything that put advertising outside of marketing. It’s even in the academic “4P” definition of marketing (“Promotion”).
Marketing is the message.

Advertising is how that's communicated.

Using a billboard or a TV advert is not marketing.

Of course, marketing needs to be advertized. Else you'd just be sitting around a confernce table all day. Sooner of later the (marketing) message will need to be...advertised.

And yes, the medium can be the message. But a magazine advertisement is not a brand style guide. Tradeshow swag is not a tag line.

It not a question of placement - inside or out - it's simple proven definitions.

You’re welcome to dream up your own definitions, but then don’t patronize others: https://en.m.wikipedia.org/wiki/Advertising
Note the opening five words:

"Advertising is a marketing communication..."

Your tone is unnecessary and off-target. The above quote from line one is exactly what I said.

You don't just wake up, roll out of bed, and advertise. Well, you can but waste a ton of money. In any case, that message needs to be crafted. That's marketing. Advertising is how you disseminate that "plan."

Logo - marketing, not advertising.

Style guide - marketing, not advertising.

Positioning of the brand - marketing, not advertising.

And so on.

Marketing is the plan. How you wish take and place your brand / product to market. Advertising is the communication of that to thd market. Advertising is what happens when the meeting ends and its time to engage the market.

Marketing = what we have to say and who we wish to say it to.

Advertising = Got it. Let's see what tools we have to best make that happen.

No dreams. That is how it happens.

Folks are getting bound up in shallow semantics in this whole thread and are missing the nuance in your distinctions.
It's not shallow semantics when what they're saying does not reflect the way these terms are used by many (most?) professional marketers.
Putting advertising outside of marketing is not a nuance.

Advertising is part of marketing.

I never said otherwise. What I did was distinguish it's definition. That is, just because you are spending momey on advertising does not mean your are properly marketing. That is, one P does not a Four P's "cycle" make. Full stop.

Futhermore, of course marketers will say they control everything (i.e., including advertising). Now let's go ask an advertising agency if they agree. Let's go ask a promotions agency if they agree.

I'm speaking about the process and activities; devoid of typical biz structures and models that manifest those. It's a fool's errand to discuss the latter without first understanding the the basics, the foundation. The fact this thread is off target proves that point precisely.

They're reading what they want to read and have failed to substantiate their position otherwise. One link to Wikipedia? Which only confirmed that was said.

It's simple. It's called Advertising for a reason. The outputs are called Advertisements for a reason. Whether that's within Marketing's "power grab" or not is not really relevant.

The funny thing is that in most consumer faced products advertising is generally outsourced to a media agency that does all the work: both creative and media buying (say TV ads, press).

Obviously for software and B2B it is a bit different, because budgets are often smaller and there is more pressure for A/B testing if there is any Return on Investment.

For me "promotion" is more like "price strategy", but they put the word into the 4P since it fits nice.

A conversation involves both listening and talking. Good sales people know that they have to "diagnose before they can prescribe" which means they must elicit symptoms and confirm need and fit with product capabilities. Really good sales people recommend other products when theirs is not a good fit. As the deal size goes up you do much more listening than talking.

Many firms that don't advertise--or do very little advertising--and are still able to generate leads, that's why it's normally included in marketing as one of many channels.

Effective marketing people also talk and listen to customers.

> Contrary to myth, successful sales is about listening, not talking.

I've been in pre-sales for about 8 years now. From the vendor and reseller side. Mostly on the technical side (SE) but I also know the process side of the account executive (AE) very well at this point.

Yes, you need to listen. But you'll never sell anything if you can't articulate a destination, lay out the path and showcase to the customer how what you're representing will benefit them more-so than the products you're trying to displace or something new that will bring with it a myriad of gains for said customer. If a customer is always telling me what they need from me then I'm not providing any value. And, honestly, it's very rare to find a customer who's ahead of a good sales team. We have full access to PMs, internal business units and access to far more insight to our bits and pieces than any reseller or customer. Don't get me wrong, I'm not saying customers can't be experts. But I'm here to know and bring things to the plate that they just can't.

Understanding your customer is often times more valuable than listening to them outright. I've found paths for the customer that has helped them avoid making mistakes, saved them money or improved their operations through paths they hadn't considered or didn't know existed. Good sales teams work hard across the board through strong technical positioning as well as strategic deal creations.

There are sales teams that rinse and repeat for every interaction and then there are sales teams that are looking to help their customers, trying to find where the wins are for the prospect. I've walked away from deals by telling a customer we weren't a fit for them. Sales gets a bad rap, but there are some of us out there that walk into every conversation not with the only intent of closing quota, but trying to make a positive impact.

> Yes, you need to listen. But you'll never sell anything if you can't articulate a destination, lay out the path and showcase to the customer how what you're representing will benefit them more-so than the products you're trying to displace or something new that will bring with it a myriad of gains for said customer. IYes, you need to listen. But you'll never sell anything if you can't articulate a destination, lay out the path and showcase to the customer how what you're representing will benefit them more-so than the products you're trying to displace or something new that will bring with it a myriad of gains for said customer.

But you don't know where the customer is trying to go...you don't know their pain...you don't know their priorities...

Without listening.

I realize this. Which is exactly why I said that "Yes, you need to listen". The parent comment responded to implied that was the only way.

If you don't listen you can't do what I stated above. And if you can't do what I stated above then you're not going to be able to help the customer and, ultimately, not be all that successful in sales.

Case in point... I had a customer years ago about to spend roughly a million dollars on a remote site upgrade architecture we had been jointly working on for about 6 months. In the background I was tracking a new product that would make their initiative cheaper and had both better ROI and performance specs due to refreshed hardware.

I made sure to present this, get all the information in front of the customer, engage in discussions using our PM and derive a strategic deal that would save them money over the three year term for buying a new product early.

They didn't do it. My counterpart appreciated the option even though it would have slipped their project by 2 months. Him and I are still friends even though I've moved on since then, but the moral of the story is he still brings that up because, in hindsight, he said he should have trusted our proposal. They spent more, got less and had to upgrade earlier due to unforeseen circumstances. Part of it was bad luck, the other part was a cognizant decision he made against the sales team better judgement.

I listened. I knew the customer very well, in fact. But I had knowledge and experience with the products that outstripped his for navigating this situation. That's how a good sales team operates.

> Understanding your customer is often times more valuable than listening to them outright.

Listen is a big word, one has to take all meanings into account.

Came to say exactly this. As a first time entrepreneur its important to learn how to spread ideas. Sales comes after.
(comment deleted)
Great summary on sales and marketing but neither is a monolith.

Sales can best be distinguished by indirect sales and direct sales.

Direct sales is where you go out and find clients.

Indirect sales is where you go out and find partners to bring you clients.

You don’t buy Coca Cola from Coca Cola. You rarely by HP from HP.

Companies tend to be more successful when they find ways to grow using “channels”.

This is a good summary of finding your path toward channel sales:

https://www.entrepreneur.com/article/297479

This is a good kit to start a channel sales program:

https://chanimaluniversity.com/product/reseller-program-kit-...

Has anyone had success doing B2B SaaS sales using cloud marketplaces like AWS marketplace, GCP marketplace, Azure, etc.? I wonder if that qualifies as "channel sales".
I think any third party taking a margin off your sale to help facilitate the transaction constitutes a channel.
Stripe isn't a channel though. The third party in question needs to actually do some work to bring you traffic / leads, not just do the mechanics of processing the transaction.
I did a bit with instances of an Open Source deep learning server of mine, for three years+ now. Made up to 1.5k/month, lower now but it's on my plate to revive it. It's provided side money to our service/ software business.

Keep in mind there's a 30% cut from AWS, plus if you're in the EU, you need a tier like payoneer to channel your revenues back into the EU.

IMO, they are failing to be good distribution channels overall, but as currently done, can be a nice vehicle for early POC/trialing phases.

Good distribution channels solve three aspects:

- Logistics: Technical delivery - pretty good, as it's cloud as usual, with the bonus of solving how to run on the customer's side of the trust boundary (vs. normal centralized saas), + pricing features like app-defined utility fees

- Marketing: Cloud marketplaces fail to do demand gen (low-traffic search, no promotional campaigns, ...), as opposed to engaged partners who will

- Sales: Trialing is better than an on-prem thing but they harm success by not having a person involved nor allowing you to know who your users are, so overall, hurt closing. They are good-ish on solving procurement/invoicing

So again, pretty bad as an overall distribution channel, but for handling the paid POCs of a sales/marketing pipeline defined elsewhere, they can be nice.

Long-term, I think these can be massive, but they're currently immature/underinvested/etc. Ex: hw fee + 20-30% sw fees for such a poor distribution channel is quite unattractive for most serious b2b partners (distribution partners normally take 5-15% and do much more work, not ~50% for so little), so looks like a symptom of PM fiefdom politics vs senior leadership investing in these to be big. They could take Stripe's 1-3% payments fees, add 5% hands-off reseller fee, opt-in for special programs for another 5%, and poof, multiple $B businesses.

> diagnose their needs and only engage with firms that will benefit.

I have done technical sales-like engagements and this is the number one pattern I see from relationships that went well. The customer determined, for whatever reason (rightly so) that I could solve their problems. So they opened up and explained what the problems really are. If you can't get this, you can't help someone.

Lean Customer Development by C. Alvarez.

Solution Selling by M. Bozworth

Bob Moesta's new book has some good pointers on it, it's currently on sale on Amazon: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progr...
This book is great.

Bob’s background is in engineering and it feels far more accessible to me than other sales books as a result. I’ve been trying to get my head around this stuff for over a decade. The ideas in this book have made me feel comfortable about selling for the first time.

(comment deleted)
I just finished this book and I think it's the most down-to-earth approach towards selling. It even suggests an alternative title for "salespeople" that wants to help others make progress, which would be "concierge."

Looking forward to digging deeper into the Jobs-To-Be-Done theory with Clayton Christensen's book on "Competing Against Luck"

A lot of good recommendations here.

I think that selling, especially the selling you’re talking about has a lot to do with mindset. I am also an entrepreneur and I have found for my own sales process that mindset and a bias toward action have produced more results and a more comfortable, natural selling style that fits me personally rather than trying to sound like someone else or use someone else’s techniques.

For this I highly recommend “sell or be sold” by grant cardone. Ignore the macho bravado, and take the mindset of sales that he has. Really helped me a lot in selling myself and selling my company rather than selling a product (although it la good for that too). I also recommend “if you’re not first you’re last” and “the 10x rule” also by grant cardone. Good luck!

As an engineer turned founder, your instinct to jump in and start doing it is correct. It’s hard to learn from books. I never did, neither did the successful engineers turned sales people that I know. The key is learning to read each situation so you can apply the right approach. You also seem self aware which will help you learn faster.

My biggest advice is get a coach/mentor/consultant who you talk with once per week to get feedback. This is how professional sales people learn in practice (eg from a sales manager). This will accelerate you learning by a factor of 10 versus doing it yourself. They will help you read each situation and push you to focus on the right places. Otherwise it’s easy to flounder on the wrong ones.

RE metrics- closed business is the only one that matters! Do whatever gets you that as fast as possible.

I wasted a year when I first founded Amplitude trying to brute force it myself and closed a grand total of two contracts for $36k. After that I ended up working with a guy named Mitch Morando and got from $36k to $1M in ARR in less than a year. He cost me $5k a month and increased our market cap by $20M, it was well worth the investment. I’m happy to make an intro if you’d like.

Good luck on the journey ahead and I’m excited for you!

Out of curiosity, how did you land on the concept for your business?
The short version is we saw a big gap in the product analytics market when we were building a consumer app. We were going to work on building a company no matter what and it was the best opportunity we found. B2B was much easier than consumer for us. All you have to do is build what your customers ask and then they’ll pay you money!

I just did a podcast on it if you’re curious: https://theboostvcpodcast.simplecast.com/episodes/ep98-the-e...

Awesome, will check out the podcast, thanks! Congrats on the success btw! Just picked up Mitch’s book on Amazon, as I’m always keen to add to the sales toolbox.
What did you learn from Mitch that you could not do yourself?
"guy named Mitch Morando and got from $36k to $1M in ARR in less than a year"

I am very curious as a bootstrapped founder myself. Would you be willing to tell us more on some of the high level things Mitch Morando helped with ? What bottlenecks did he solve that you didn't/couldn't know ?

I'm also a YC founder (Py) and worked with Mitch. He's been an invaluable mentor to me not just in sales but also in general COO advice. Could not recommend working with him enough. It is a Privilege to get to work with him. He has a wealth of experience that make his monthly rate easy easy ROI.

We went from literally $0k ARR to high 6-figure ARR in 8 months before getting acquired. He taught me everything I know about SaaS sales.

Mitch was recommended to me originally by Peter, CEO/Co-founder at Segment.

First time founder here who came from sales at a big consulting firm, and then and then had to develop the whole marketing and sales stack for our startup.

Most of the books recommended in this thread assume that you're working for a established firm, with product / market fit, etc.

Clearly that's not the case for a start-up.

Read up on what Pete Kanzanjy publishes https://www.foundingsales.com/ - it covers the the "founder-led sales" phase.

How I did it:

- you interview as many prospects and customers as possible

- you understand what keeps them up at night, what specific pain points they have, the language they use to describe their situation

- you shape your messaging to solve those specific pain points, using their own language

- wrap your messaging into a story - the worst you can do is "problem / solution". people don't buy that way. people buy change, and you use the story to communicate that change.

I wrote a totally too long Medium post on the whole topic:

https://medium.com/@larskamp/the-5-cs-an-operating-framework...

as somebody else pointed out on this thread - be read to deal with objection! You'll likely collect 9 "No's" for each "yes!"

When you get to larger firms, there's a lot of support of sales (marketing but also engineering) that involves creating awareness, building the funnel (leads etc.), supporting sales reps in various ways, building products that customers actually want, etc. But none of those things actually involve directly asking for a PO, working on customer relationships, and so forth.
Is this how you substitute experience in an industry? As in the “we built this because we needed it, and it turns out a billion other people did, too” story?

It sounds like everyone ‘improves’ their offering based on feedback - but some folks seem to ‘just know’ what they are going through, and that somehow resonates with others.

I’ve always wondered if there’s a difference between approaches or if it’s all just window dressing.

Heads up. The foundingsales website took my username and password but did not give me access to the material. Instead its putting me through a "Buy the Book" or "Register to Read" cycle.
That’s odd. There’s a couple dozen people on the site right now.

What browser are you using? Sounds like maybe a Memberspace issue with a config you have?

Check to see which of these chapters you can access: https://www.foundingsales.com/table-of-contents

I just tested this with a new account and it’s working fine from mobile Chrome. It returns you to the home page on registration so perhaps access one of the chapters? Like this one to start: https://www.foundingsales.com/1-mindset-changes
I have the same isssue. I think it may be a Safari issue. Works fine for me on chrome not Safari.
That’s super annoying. Are you able to access this hyperlink while logged in in safari? https://www.foundingsales.com/10-early-sales-management

It might also be that the redirect after registration goes back to the home page, and the chapter buttons are below the fold if one doesn’t scroll down. Probably would be better to redirect to table of contents after registration. I’ll see if that can be configured through Memberspace.

Having problems with Firefox + Linux. Works ok on Chrome + Linux.
I had to allow third-party cookies for those 2 sites
Was about to post Pete's book too. Go read it!
+1 to Founding Sales — it's great, and Pete is great as well
Interesting!

> you interview as many prospects and customers as possible

Did you do that before or after completing your product / service?

both.

this is 4 years ago, the market we were going after were the cloud warehouses like Redshift, BigQuery and Snowflake.

In the beginning, we just had an idea for a specific product / service. but we knew that the customer would be the lonely data engineer in charge of building the analytics stack.

I started with cold outreach via my network and linkedin. I would use pretty broad language around data warehouse usage, to cast a wide net with terms like "usage, performance, metadata, etc.", and cover all potential use cases. Engineers are always short on time, so you need to be affirmative, authoritative and present a clear ask that shows what you want and how the engineer will get value out of spending 30 min with you.

Of course I pulled the founder card, and that does help. I made it clear that we don't have a product, but working on building one. Turns out that most people are helpful, and want you to win!

The first signal that you're onto something is when they reply to your message, and are intrigued.

we built our first product around that feedback. Companies like Postmates, WeWork and Udemy bought version 0.5!

I made a point out of keeping in touch with every customer, and do a quarterly check-in. What's changed? What are your plans? For this coming week, month, quarter and year. Where do you want to be in 2 years? What problems are you trying to solve for your company? What are the expectations for you and your team? What tools are you using to solve that problem? What tools have you looked at and decided to not use them, and why? Etc., etc.

I rolled around in THEIR situation, trying to walk in their shoes. We'd talk for sometimes 90 minutes, often in person here in SF, over lunch. We'd often not cover our product until the final 5 minutes.

Of course, that's a huge chunk of time out of your calendar. Huge opportunity cost, in particular for a founder.

So here's actually something I'd do different. We hired our first sales reps after our first 10 customers. That was a mistake. Our product was very technical, it's not like selling email software. So you need a technical rep. Our first rep was a class act, but let me tell you, it was a goat rodeo for him.

Rather, I should have hired a customer success person, and have them do the quarterly check-ins. That way I could have kept selling. Then let the customer success rep also write (technical) blog post, customer stories / case studies, and documentation. You're building out (credible) marketing materials that build the top of your funnel.

Wow. Thanks a lot. That’s very specific and actionable. Any other thing you would do differently this time around? I’m in the middle of starting something new myself.

BTW: feels like you could write an entire book about your experience ;)

#1 thing - I would raise less money for our seed. We raised $4.2M incl a note that converted from the angel round.

Too much money gives you a false sense of security.

> Rather, I should have hired a customer success person

Also called a Field Application Engineer in some circles.

> Then let the customer success rep also write (technical) blog post, customer stories / case studies, and documentation.

Also sample code, sample scripts.

In the 00 years I started my first company with a product called "Search Engine Optimized Distribution of Pressreleases and -communication over Blog and Web 2.0 Networks".

Today we would call it Corportae Blogging.

I created a product, a blog CMS (very poor on the M) and wanted to convince companies of SEO and blogging. Non of it where anywhere on their radar.

And 0 sales experience from my side.

I fail and realized I needed sales experience. So I applied and became a key account and a slazy company which sold crappy websites to estate agents.

Worst job ever. Learned a lot.

If you want to really learn sales, start selling. Just change your job for a while.

I helped run a small startup a long time ago. I helped shape some sales strategies and went on client pitches. Our main approach was to find the "pain point" of an executive in the company (we were B2B) and break through to them that way. To find the pain point you have to ask questions, which helps engage with the person you are selling to. Sometimes you shape your questions to get the client to think about potential pain points that your product solves.

We kept crafting our message over time, using email and cold calls, and used a lot of copywriting books to find messaging and pitches. I think the best one was The Copywriter's Handbook. Straight and to the point book. It's more about advertising, but messaging is key for sales, too. A headline is basically your elevator pitch. I think we also used the book Spin Selling.

As someone who wouldn't in a million years buy anything from anyone who was trying to sell me something, how do I learn sales?
You can't till you over come this mental barrier. There is this great book called To sell is human. Try giving it a read.
Come on now, you buy things every day.

The secret isn’t making everyone say yes but to have as few people as possible tell you no.

Be interested in solving real problems by providing real solutions. Make your pitch, answer questions. Then stop talking or else you'll talk your customer right out of the sale. Above all, be human and be open with others. They aren't buying your product or service, they're buying YOU.

Book: To sell is human. Daniel Pink

This is honestly THE BEST, all-in-one resource I found for the exact same question I had - https://static1.squarespace.com/static/57daf6098419c27febcd4...

Secondly, follow Close.com blog, there is tons of great sales insight, and download their Startup Sales Resource Bundle - https://close.io/resources/startup-sales-resource-bundle

Thirdly, watch Steli Efti's keynote about startup selling https://www.youtube.com/watch?v=55z5yl_naco&feature=emb_titl...

You're all set ;)

wow that was a wormhole. thanks for these. spent half of my day, but i have a much better understanding now what I'm dealing with.
Oh boy - I didn't realize a question could be so topical. Another first-time founder here (engineer turned founder) that is currently in the middle of learning how to do the b2b sales process (which I'm assuming is what you're doing, if you're interested in b2c, I'm not sure how much of this translates). Needless to say that: (1) I'm most certainly NOT an expert (just someone figuring this out as well); (2) I'm super-duper interested in the responses here.

First things first, I think before selling, my understanding of sales was largely grounded as an "art", and by far the largest turning point in my understanding has been that sales has a pretty large "science" component to it as well, by which I mean tried and true repeatable steps that can be applied consistently.

As a founder, before sales, you need feedback. Assuming you don't have product-market fit (which you almost certainly don't know, because you don't have users), it is MOST important that you talk to customers to get a handle on what they need. The two books I found most valuable here are: - The Mom Test - Talking to Humans

(The Lean Startup has a good section on this as well; if, like me, you haven't reread it since starting a company - I would highly recommend doing so, you grok so much more than when you first read it without any experience to ground it to.)

Once you have some intuition around your market and that your product is actually tackling the right problem. I would read Founding Sales (https://www.foundingsales.com/). I was recommended this book by a founder-friend who told me "Literally stop whatever you or your team is doing and take the next two days to read this book" and I'm glad I did that. The book has given me a solid anchoring, vocabulary, and makes a compelling case that founder-sales are fundamentally different than regular sales: regular sales are what happens AFTER you have a repeatable process, founding sales requires much more of a product mind to rapidly integrate feedback and live-iterate on the product.

From there, you'll realize you have two skills you really need to learn: marketing and sales. Broadly: marketing is about getting leads, sales is about closing them.

Marketing: There are a whole bunch of books and articles I've been recommended on marketing (Traction being one of top recommended ones). However, after having done a lot of this I'm not convinced that this is a good use of time as a founder. So much of what I've heard / seen is that your first few customers WILL be warm intros from within your network. So a better use of your time may be a LinkedIn subscription and to go through the network of: your VCs, any former companies you've worked at, any school you graduated and shamelessly ask for intros. A good article that popped up on HN recently was: https://stripe.com/atlas/guides/starting-sales. (Also, for the theory of marketing, I personally found Crossing the Chasm a solid book to contextualize what phase of selling I was in and how it might change over time.)

Sales: Is hard. The best advice I've received is: remember it's about them. Not about you. When someone is gracious enough to take a phone call with you, do not immediately pitch them. That makes it about you. Instead, ask them about their process and the pain point you address. This helps both: you discern if it's a real painpoint, them realize that they have / the magnitude of that pain. Two frameworks that have helped me are: - BANT: https://blog.hubspot.com/sales/bant - MEDDIC:

thank you for sharing this helpful information