Tips for Founders Doing Sales (From a Founder) | Hacker News Reader

Tips for Founders Doing Sales (From a Founder)

micael.substack.com

196 pointsmicaeloliveira41 comments

I'm an engineer turned bus-dev/sales person. I found the transition very difficult and was recommended to sign up for sales coaching. It was excellent advice and I learned a lot about my inherent weaknesses when it comes to selling and how to compensate for them. I wrote a few of my lessons on my blog. A bit dated but perhaps of value to others:

https://www.curiousjuice.com/blog-0/bid/134157/Sales-trainin...

https://www.curiousjuice.com/blog-0/bid/135376/Secret-to-sal...

interesting. thanks for sharing!

"A bit dated"? That's not exactly selling it... (I kid, I kid)

How did you go about finding the right sales coach? Was it a 1:1 program or something more like a class?

Hi there. I didn't really search. My coach was highly regarded in my company, having trained everyone from our SVP of Sales down to front-line employees. I liked the methodical assessment they used to discover your weaknesses (it's called Objective Management Group) and my coach made himself available for unlimited time but for a max period of six months. I liked this setup as it didn't feel like fixed hours but more like I could call/email him anytime and all the time.

I should add that he led me astray at times insofar as not all his advice worked well. But perhaps that was part of the learning too.

I found these write-ups very valuable. Thank you!

> Get to know your customers before selling to them...The easiest way to go about this is to solve your own problem.

The headline is good advice but being your own first customer is rarely good.

First the bad:

1: if you have problem X and have the in house skills to fix it, it’s likely that your potential customers can fix it for themselves too.

2: you are not the same as anyone else: you can fake yourself out by believing that your potential customer thinks the same way you do. If your prospects are quite different from you (say you’re a programmer writing a tool for doctors) you’ll work harder to understand their real and perceived needs.

But sometimes this is good advice:

1 - Even if you are different from your customer (say you’re writing something broadly applicable like a web site design tool for small business), “eating your own dog food” will find bugs and infelicities faster.

2 - if your customer has the same needs as you perhaps you already know how to meet said customer easily, such as trade groups you’re already in.

In general the advice in this post was pretty basic and generic but I didn’t want to let the issue above pass I commented.

SaaS is less about the capability and more the opportunity cost. Anyone can do anything with the appropriate amount of human capital and resource investment. It’s more can you provide the service cheaper by specializing and providing the service for cheaper than they could do themselves?

Or providing the same service but much better, and at a slightly elevated price that's justified. Took me a long time to learn that I can charge a lot and still add value.

This is indeed a hard lesson to learn. For me I used to charge less out of insecurity that I will lose the customer. But later on I grew some backbone to ask more. It depends on customers as well. Now I simply steer clear of prospects too driven by price rather than value.

Exactly. I'm a professional programmer. I certainly could create my ideal text editor, from a technical point of view. It would probably only take me a few days to get the essentials covered.

But then it would probably take another month or more to polish it and fix a few annoying bugs. I'd want to integrate things like themes for when I feel like a change of style. And language servers for when I want more powerful integration, obviously. Oh, and integrated Git support is all the rage right now. But best make it modular in case my next client prefers Hg.

Then there would be a fortnight when I got obsessed with fuzzy string matching for search and replace and how it might interact with multiple selections to create a highly efficient quasi-macro system. That would inevitably lead down a rabbit hole of reading a dozen papers and watching several conference talks. OK, at least I might have got a nice speaking gig at the end of this one, at least if there were any local meet-ups actually happening by then.

But by that time it's mid-2021. I still haven't actually got a better editor overall than half a dozen choices I could have used the day I started. I also haven't made any money for the last three quarters, and the bills are coming due.

Just because I can fix something for myself, that doesn't necessarily mean I should or want to.

I think you make good arguments, but #1 is a typical techie argument: Why would I ever use $SaaS if I could just cobble something together with rsync and Excel? Well, because $SaaS is a much more polished product with all the headaches removed.

This was the basis of the scepticism towards Dropbox in that infamous HN thread. In the end if I'm either an individual consumer or a business consumer I just want my problem solved really well and not have to always build a custom solution in house for everything.

But I can see other contexts where OP's advice applies, either when requirements are very bespoke or when the problem is little more than a small annoyance and existing tools do the job just fine

I've worked in multiple startups/bootstrapped enterprises that started as consultancies to pay for the development of internal tools with the ultimate goal of licensing the tools. It doesn't always work but its the least bad validation strategy I've seen.

I find 1) and 2) of your "bad" items to be more nuanced. Mostly because outside of software development most industries do not have the capacity to build a solution outside their particular flavor of a problem, and they don't do it internally. They hire consultants to do it, and there are enormous inefficiencies that prevent their solution from turning into a product.

Disagree. Any company that employs electrical engineers "has the in-house skills" to design their own office light fixtures and repair the microwave in the breakroom, for example. But is that a good use of engineering time?

It's just a recap of the infamous HN DropBox argument.

> Don't promise features you are not planning to build and align your prospects expectations with.

As an engineer turned sales for my own indie company (15 employees today, had 0 when I started doing sales) - I partially agree with this point.

Don't build something custom simply to win a new customer. But there are a few times I've listened to a prospect describe their need and I though, "huh, that kinda wasn't in my original vision but it could be useful to other customers/markets." I'd subsequently tell them the feature is on the roadmap and pitch a higher price than I normally would.

Sometimes they bite, sometimes they don't. But on a few occasions, they came on board, I delivered, and that feature became a popular differentiator with other prospects.

> 15 employees today, had 0 when I started doing sales

That is impressive, especially sales and marketing. How did you handle marketing when starting out alone? Was it mostly online or you visited local customers? I find getting foot in the door most difficult thing to do.

The first customers were definitely the hardest. I didn't do any classic marketing, just cold calls and emails. It took a few months to get the first paying user. I did target a specific niche.

I then went in a road trip around the northeast (literally camping in a tent at the nearest KOA or park) hitting different areas where customers were. I'd stop in town, call them up, and tell them I was passing through (which was kind of true) and ask if they could meet for a half hour. I got some of my first meetings that way.

It was extremely inefficient but helped grow the initial user base. It's definitely not an approach I'd recommend to someone - it's kind of ridiculous but it worked.

That said, the customers I was targeting were all part of the same trade association and the word spread that I was actually doing something pretty useful. That led to new customers and a lot of word of mouth.

I only seriously started with traditional outbound marketing this year, which is my 8th year in business. Other than that it's been direct outreach, word of mouth, and attending conferences and drinking my ass off with potential customers (not ideal, but every association has its own vibe and sometimes you gotta do what you gotta do).

Building partnerships with like minded entrepreneurs in your industry is a good approach too (referrals, integrations, etc)

All this said, it took 4 years to make enough money to pay myself and 5 years to hire my first employee which was a customer support manager. "Delegating and elevating" is magic and led to more time to focus on growth. I did a lot of freelancing in those first 4 years to make ends meet. It could definitely be done faster, but I was way more of a n00b than I realized at the time (isn't that always the case?)

Thanks for sharing your story!

Change Request.

Get the customer to pay for it. $300/hour for custom development consulting.

That seems like an awfully hostile business model. Hopefully the cost of switching to your competitors comes in at less than $300/hr.

One of the best tips I received for sales: when trying to sell a pen, don't focus on the features. Stop and ask the customer - what are they looking to do with a writing instrument? Go as deep as possible in understanding their need in that conversation by asking questions. Once you understand the need - work out how best to fit the pen you're selling to their needs.

Two benefits of this approach: the customer does most of the talking. And by listening intently you know the things to say to help the customer see what you have matches their need.

Also, if in your conversation with the person you find out that they actually need a paint brush instead of a pen, don't try to sell them the pen! If you try to sell them something they don't need, you either piss them off by looking like you don't understand them, or you piss them off once they bought the pen from you and realize it won't work for them.

Instead say that probably you don't have (currently at least) what they are looking for, and if they need help in the future to contact you again.

You're often not selling what you think you're selling or not selling it to the person you thought you'd be selling to. Approach your sales process the same way you did your product development - you need to beta it. Get a few early customers in and really learn from them. How did they make the decision? What do they think the main benefits are? How are they using it? What would they tell a friend? Who influenced the purchase and who paid for it?

Three really good takeaways from the article: Be passionate, don't oversell and follow up. I've seen each of these trip up other founders and... ahem... me. There's another kind of overselling the article doesn't mention and it kills deals dead: selling after the buyer says, "ok let's go." I see this all the time in founders who are selling, mainly because... well... they are passionate.

The most important thing to remember when selling anything, is to understand whether or not the person you’re facing wants to buy it. The word sales people use is “qualification”.

If a person is qualified to purchase, selling them your product is a no brainer. When you qualify a person wrongly, you’re going to regret it. Waste of time (yours and theirs) and money (mostly yours).

> 5. Listen and improve your pitch.

> Listen! You will get a lot of feedback from customers during your first calls, use that feedback to make adjustments to your messaging and improve your pitch.

It's easy to say just listen to your customers, but it's a lot more complex than that.

People will often give bad advice in an attempt to be polite, or because they're not understanding something.

It's not just about taking customer feedback at face value but also trying to figure out if you're getting the feedback you expected. And to be able to draw out as many insights as possible. Something that's rarely if ever straightforward.

All I can add here for founders is, "don't let sales corrupt your product goals" and "don't let revenue be the end-all of your company".

I have seen too many young, inexperienced founders get caught up in the hamster wheel of searching for earlier-than-ready-for revenue at any cost, on the VC's schedule, and being slave to that dimension of performance while losing sight of everything else. It may feel good momentarily, but you'll look in the mirror and wonder who's in control of your life. And why a couple months down the road you're trying to slap lipstick on a pig and sell it to anyone who knocks.

It may be harder, but make that choice earlier and be what you want your company to be, not something else.

As part of an accelerator I did with my startup [0], I had the chance to check out a talk by Scott at https://salesqualia.com/. While we have less of an enterprise sales approach and more of a bottom-up distribution approach, I still found Scott's structured approach to thinking about sales really useful. I recommend people check it out.

0: 0: https://kitemaker.co - the product management and collaboration tool that's crazy fast, loaded with hotkeys, and has deep integrations to your favorite tools like GitHub, Figma, Slack and Discord.

Most important realisation for me personally: keep emailing.

As an introverted dev trying to sell I often assume silence means they don't care and they hate me. I've learnt this is almost always wrong - the recipient is typically just busy or indecisive. Stay polite/respectful/human but keep at them and don't let the void kill you.

Still figuring out the details but getting over that was quite a profound feeling and has turned out pretty useful in life generally

> keep emailing

The same possible customer, with exponential backoff?

Or you email the same person regularly say once a week?

Am I the only one thinking that these 10 tips for founders doing sales are shallow and useless?

At least the HN conversation is much more interesting.

There's an excellent book on this topic by the founder of TalentBin: https://www.holloway.com/b/founding-sales

He also writes it from the perspective of a founder learning to do sales for the first time.

How do you actually transition from selling to closing? Eg, you start hearing the customer make "buying" comments and know you need to transition, but what are tactful/smooth/effective way of doing that?

3 is only an issue when you are small. Everything's different the moment you have spare funds and engineering manpower.

The advice says "Don't commit to things you cannot deliver on." No matter how big you are, if you can't deliver, this is the correct advice.

The qualifier is that in true enterprise, you can do proserv deals to ramp them to full size, and you can sell roadmap pretty hard because a lot of the time the decision and the implementation happen in different quarters or years. So it definitely does honour their process to let them know something is coming if they're making a 5-10 year decision and something is only a few months out. You definitely have to follow through, though.

This is great stuff. Want to come on my Sales for Nerds podcast and discuss in more detail?

Ask for the order. A salesman who doesn’t ask for the order is just bullshitting.

Sales is easy if you're rich and connected;

Depends what you are selling.

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