My first year in sales as technical founder | Hacker News Reader

My first year in sales as technical founder

fabiandietrich.com

111 pointsf3b564 comments

> Why do I even need to do sales?

> When looking specifically at bootstrapped (self-funded) SaaS startups, this is a valid question. There are many profitable startups in the low-end B2B space ($10-$50/mo) that exclusively rely on marketing. These are the perfect lifestyle businesses that the indiehacking community is dreaming of. But they’re very hard to pull off, and leave a lot of money on the table.

Fellow technical co-founder-turned-salesperson. I'd like to add something here.

In previous businesses I relied on marketing, SEO etc.I thought "they're the gift that keep on giving" whereas sales is effort in value out. Not only is that wrong, but SEO / ads take time. For an early-stage company / product where iteration is key, sales is the fastest way to get signal.

Imagine using web conversions as the driver for iteration. It takes at least a week to kick off some campaign, months to build up, and months to have interpretable data. Plus no one's going to just tell you "no"! With sales, you can send 100 emails and in one night get some real signal. You might even get an inkling of "that's not going to work" or "ok I'm interested". In a compounding feedback loop, that is often the difference between a company that pops off and one that fizzles

As a co-founder (tech background but haven't coded in a while), I got comfortable with sales best when I hired a sales coach. There are so many things to learn in sales and a coach is often the fastest way to assess your inherent weaknesses and address them head on.

I paid $2k/mth about 10 yrs ago; at the time I felt scared to spend so much but once I realized it was an investment in me, and I put in the time to learn, I can safely say it continues to pay off even now. I quite enjoy sales now. Not saying I'm good at it but certainly a far way from "I hate sales and would much rather code".

Do you think that sales is among the many realms where freely available quality instructional material has become ubiquitous in the past decade? Not that it would ever work as a full stand-in for a paid coach, but it might be enough to bridge the gap for some of us.

Yes I think possible. 1. sales aptitude assessment tools like Objective Management Group (the one I took) help you identify core weaknesses that are critical to understand and work on. 2. Recording your sales calls (assuming you're on the phone) and then asking AI to critique it and coach you, with the above assessment as context, could be very helpful.

If you're disciplined I think the above approach may be a pretty good stand-in for a real coach. Or at least help you evaluate a coach better should you choose to pony up for one later.

I'd be careful sending raw audio to public APIs given the sensitive commercial info. A local pipeline with Whisper and Llama 3 is viable now and solves the privacy issue. It also keeps the long-term inference costs much lower.

Llama 3 is far from cutting edge now and the value from quality analytics would far surpass risk adjusted odds of your info leaking.

Its like acting. Some people can do it without acting coaches. But it’s best if you invest in them.

How many months did you do it for until you felt comfortable on your own?

My coach has a max timeline of 6 months so you are forced to swim on your own. I felt like I had the hang of it after about 4 months so stopped about then.

(sorry for delayed reply; I don't think HN notifies you of replies?)

How did you find a sales coach, how did you determine which was the one for you / any good at their job?

Mine was a referral from the VP of sales (the coach was his dad and many of the reps in our team had been coached by him). Fwiw, his name is Rick Roberge. I think he still coaches. He's can be a bit antagonistic but he's very good at what he does and I'm glad I hired him.

This was super useful. As a technical person willing to learn sales, the numbers that you showed at the different stages of the funnel shows that is all a numbers game and rejection is the norm. From 487 connections to 2 paid clients. Great post!

I concur. Really great post! Been an engineer for a while, starting to prepare to put together SaaS products, so this will be useful to come back to. Thank you, OP!

Back in the days, I did the first 2m in ARR at Stream myself, it was kinda hard :)

Nice to have a team in place these days, but I still show up for the largest deals to support the team as needed. (140 person company, i think this always stays part of the founder tasks)

What I understood from this is that LinkedIn and Email outreach are quite effective for leads. 1-on-1 conversations and the obsessive focus on solving problems different customers face do feel the right way to go about sales.

We just launched Fostrom [1], an IoT Cloud Platform designed for developers. I was wondering what else have others found effective in this space to do sales and outreach?

[1] https://fostrom.io

The calendly thing is interesting. I get a fair amount of prospecting outreach on LI, and if anyone asks me to book a slot myself, it's an instant no. I feel like you can't be bothered to actually engage with me, that you are not prepared to do this tiny bit of work. It almost feels disrespectful?

Am I alone in this?

Anyway, is not an approach I would take.

No, I feel the same. Calendly link is a major turn off.

Generally you don’t drop the meeting link right away, that is annoying.

So you prefer

does tue 11am work for you?

no, does tue 2pm work for you?

no, does wed 10am work for you?

yes, wait which timezone are you in? central? then no, does...

Or do you mean you don't like the link in the initial email?

What’s your actual message while reaching out on LinkedIn? Do you send a note while sending a connect request?

When I was a CEO (technical founder) I had to learn very quickly that my key job was selling.

While fundraising is also a form of selling, I am specifically using it to mean actually making deals with customers as lead BD as this person described.

After 5 years there is no amount of incentives that would make me do sales. The entire job is manipulating people to work against their own best interest.

People who are sales people for a lifetime will tell you all of this bullshit about how it’s relationship based and it’s really just talking about the customer about their problem and how their problem fits in to your solution or if it doesn’t in the best case then you don’t engage with them and you find a better target submarket etc…

Probably the best sales guy I’ve ever met became a “good friend” of mine when I was CTO for a massive government weapon system.

I went out on his boat he met my kids we met each others families. He went out on his own and found a giant CRT monitor for me, so that I could start ranking up in Tetris after I made an offhand comment about it. He even called me up personally when he left that company because he was moving to a new company and just wanted to touch base and etc. and continue our relationship.

The moment he did not need my business there was nothing to be said.

That is the Peak of salesmanship and if that’s the Peak I don’t want anything to do with it.

So while I understand this person’s story, as an extremely technical person who had to do sales for years, I found absolutely nothing rewarding beneficial or good about it.

I would feel better about being a sex worker, escort or prostitute, because at least there’s no ambiguity as to what’s going to happen.

In a transactional business (You give me money I give you product/service) the majority of the time you’re trying to figure out how you’re getting fucked over, or how you’re gonna get fucked over, or how can fuck over someone and your job is to manage these fake, corporate “relationships” that are trying to constantly reevaluate and renegotiate things.

So my only advice as a technical person is “Don’t join a company before product market fit, and stay as far away as you can from business processes as possible until you don’t have to work for a business ever again”

I feel this howl. I found that sales work was forming relationships so that you could make promises, personal promises. And what drove me out of it was that, beyond a certain point, there was no way I could guarantee that the promises I was making would be met. There was too much uncertainty, too much risk. But the client, in their heart, wanted you to look them in the eye and say "we'll get it done". Real sales people could do that and then go home to dinner and bed and a good sleep. I would do that and then go home and stare at the ceiling for 12 hours.

> Real sales people could do that and then go home to dinner and bed and a good sleep. I would do that and then go home and stare at the ceiling for 12 hours.

100% this

I can’t think of a more toxic environment than the sales culture.

Go look at literally any sales culture organization and it’s an unironic copy of Wolf of Wall Street

Like poker, math only takes you so far in sales. You have to learn people if you want to succeed at selling. In fact, math is all but irrelevant for most person to person sales. Buying decisions are mostly emotional. Learning people is a skill that will translate to every other aspect of your life.

this is a bad analogy. at the highest level, poker is entirely math. the player with a better understanding of GTO will demolish someone who tries to "learn people"

I suppose I should take your username into account and take you at your word, but wouldn't a player that entirely plays mathematically be easily exploited?

I assumed table talk was at least 10% of poker. Mind games, conditioning your opponent and making reads are present in most sports.

If you play game theory optimal (GTO) then you by definition can not be exploited. For poker a GTO strategy is extremely complex where each decision you make depends on the exact situation and includes varying your decisions over time. Like bluff raising 60% of the time and folding 40% of the time you’re in some very specific situation. It’s basically putting your opponent into a situation that they can’t make a profitable decision in the long term.

It’s not really practically possible to do. But if two people did they would have 0 expected value over time against each other. If one player slightly differed from game theory optimal strategy that would give the other one positive expected value. There is no way they can change from GTO strategy to exploit you.

However, this isn’t necessarily the most profitable way to play against real people. When your opponents aren’t playing GTO, there will be some non-GTO strategy that exploits them most effectively. Like if they call too much then you should raise for value more often than against a GTO opponent and bluff less.

There's a world of a difference between "at the highest level" and your typical casino poker game. (GPs general point still stands.)

playing "GTO" doesn't mean you will destroy people, this is a common misunderstanding of the term. It means that you are playing in a way that cannot be exploited - this does not mean you're also playing in the way that will win you the most money.

Also, there is no "better understanding" of GTO because poker is an unsolved game, and the assumptions you feed into a GTO playstyle can change quickly or be wrong. The thought you can sit there like an automaton with a set strategy and win is false.

been playing off and on professionally for 20 years

> The thought you can sit there like an automaton with a set strategy and win is false.

This is provably false.

You're absolutely right that GTO does not guarantee you'll win the maximum against a fish, but neither does exploitative play. In fact, exploitative play can't guarantee you anything, which is probably why old-school pro players are perennially going broke throughout their careers (that and bad bankroll management).

IMO, currently, over 90% of pro poker players (especially live and in the US) fundamentally do not understand how poker should be played (which is why they get so easily destroyed by the new generation in online heads up).

> This is provably false.

Where is the proof?

> You're absolutely right that GTO does not guarantee you'll win the maximum against a fish, but neither does exploitative play. In fact, exploitative play can't guarantee you anything, which is probably why old-school pro players are perennially going broke throughout their careers (that and bad bankroll management).

I'm not arguing in favor of one or the other, I am just correcting the misunderstanding. In reality, you should adapt to the conditions at the table and your opponents habits, because "GTO" is only possible against perfect play to begin with, so you're always going to be playing slightly imperfectly. so is everyone, because you cannot know everything. And again, it's almost never the way to win the most money. It's a distinction not a lot of GTO nerds understand. I'm not arguing against it at all - I use GTO solvers to work on stuff a lot.

And I also never claimed exploitative strategies guarantee everything, for the same reason "GTO" doesn't either. It's a game of incomplete information. The skill comes in using incomplete information in making good assumptions - that is almost nothing to do with math. And, there are pros that have been winning for long amounts of time knowing zero about GTO theory.

> Where is the proof?

von Neuman proved it for 2 players in his classic "Theory of Games and Economic Behavior": https://archive.org/details/in.ernet.dli.2015.215284/page/n3...

Nash proved it for n-players: https://pmc.ncbi.nlm.nih.gov/articles/PMC1063129/pdf/pnas015...

> "GTO" is only possible against perfect play to begin with

This is a very common misconception, probably because GTO is usually explained as the equilibrium reached by 2 perfect players. The key insight of GTO is that you do not adjust your strategy to what your opponent is doing. If you play the equilibrium strategy and they don't, you're guaranteed to make money.

> And I also never claimed exploitative strategies guarantee everything, for the same reason "GTO" doesn't either. It's a game of incomplete information.

I didn't say you did, I was just making my own independent argument as to why intuitive play is dangerous and people often end up deceiving themselves into thinking they're winning players.

> And, there are pros that have been winning for long amounts of time knowing zero about GTO theory.

Which is why I said that, IMO, 90% of pro players fundamentally misunderstand poker (and that's not even counting the losing players who think they're "pro").

There is an entire area of math about the uncertainty of decision correctness in incomplete information scenarios. One of the neat aspects of it is that all computable optimal decision makers are mechanically exploitable if you have a reasonably accurate model of their finiteness. In the case of human minds, that just means they are a lot like you. The exploits require iterated games and are cognitively difficult (you have to track a lot of state).

Anecdotally, in my poker playing days I had a lot of success by attacking quasi-optimal play this way. Optimality is contextual. You can engineer a context that motivates suboptimal decisions in fact, though it isn’t easy.

However, at the limit, this is really just attacking the cognitive facilities of your opponents rather than the math of the game. Someone that with a similar ability to manipulate large amounts of state mentally could nullify the advantage. It is meta-games all the way down.

> Optimality is contextual. You can engineer a context that motivates suboptimal decisions in fact, though it isn’t easy.

I agree with your post but I'd just like to nitpick that this first phrase is not true, the equilibrium point is independent of what your opponent does. I'm pretty sure you know this as you then go on to describe not a context where the equilibrium changes but where it becomes hard for humans to find the equilibrium.

So we agree, it's just a small nitpick of how you worded.

That is fair point.

I definitely understand the term, I promise you. if you are playing GTO, you will destroy people. I am 100% confident of this.

This is exactly wrong. At the highest levels you play your opponent, not only GTO. No one can play pure GTO and you exploit how your opponent moves off GTO.

Maybe if you have a lot of hands and so are confident they're deviating in some hand, otherwise you risk getting exploited yourself.

The players who study GTO instead of trying to win these meta mind games have proven to do very well in online heads up while the old-school mind games guys keep going boom and bust.

I dont think online represents the highest levels of the game...

Online high stakes heads up cash games is by far the most competitive field in all of poker, for several reasons (global competition, more hands per hour, very few fish, etc).

An online $100/$50 heads up match is probably equivalent to a $10k/$5k live game, in terms of the quality of pros you'll find grinding them.

What do you think represents the highest level of poker instead?

I don't think you've played much GTO poker if you believe this.

Other than the basics, math is not going to help you win at poker over reading people. The shoot is shuffled after each round, you can’t card count your way to victory. Hand win probabilities are basic math that most poker player just learn instinctively because it’s not that complicated.

Your knowledge of the application of math to poker is very outdated, look up "GTO poker" on YouTube.

Interesting, thanks for this.

you do not understand poker. it is a highly mathematical game with incredibly complex probabilistic strategies

You confirmed both my point and yours at the same time...

In some way or another you must toot your own horn or have others tooting for you.

A very good multiplier is doing both in a well-orchestrated way.

"1) it is highly scalable and you can easily send out thousands of emails per day, 2) it’s a fairly “democratic” form of outreach where you can achieve great outcomes with good offers sent to the right people, and 3) there’s no platform risk."

From a European citizen point of view, this framing ignores a very real constraint: GDPR.

In the EU, sending marketing emails is not just a growth tactic, it is regulated personal data processing. In most cases, you need prior, explicit consent before sending promotional emails. “We found your email online” or “legitimate interest” is usually not enough for cold outreach aimed at sales.

The risks are not theoretical:

Administrative fines that can reach up to 20M EUR or 4 percent of global annual turnover.

Orders to stop processing, which can immediately kill an outbound pipeline.

Domain and IP blacklisting by European ISPs and email providers.

Blocking or delisting of websites and services in the EU market after regulator or court decisions.

Complaints to Data Protection Authorities by a single recipient are enough to trigger investigations.

So there is very much platform and regulatory risk, at least if you want access to the European market. Email is scalable, yes, but in Europe it scales legal exposure just as fast if consent, proof of consent, opt-out mechanisms, and transparency obligations are not handled correctly.

This is why many EU companies invest heavily in permission based lists, double opt-in, and strict compliance processes. Growth without compliance is not “no risk”, it is deferred risk.

For the love of all that is holy and all that isn't, do not get your legal advice from ChatGPT. Reposting that advice as though it was your own writing, such that unattentive readers might not recognise that the legal advice was coming from ChatGPT and might mistake it as coming from someone who has any idea what they're talking about, is even worse.

IDK he might just be French, the French speak like that because they hate English.

Sales can be a legitimate interest.

That sounds like hell for new businesses. No wonder Europe is stagnating in innovation.

Scaling outreach is tricky when privacy rules change the ground under you. You could look at mailsai to help manage opt outs, consent tracking, and basic compliance steps so nothing slips. It makes outreach steadier, especially when dealing with EU contacts.

There’s an abundance of public data on people’s interests (their comments and reactions to posts), which we evaluate with our in-house AI agent to build high-intent contact lists.

That's fishy and depending on the jurisdiction it could also be illegal. I wouldn't want to receive a personalized e-mail from someone who scraped my public comments on some platform. It would seem too fucking intrusive.

I hate to be an asshole. But is a person who converted 2/487 attempts someone to follow, someone to immitate? It's a numbers game.

A more constructive way to phrase your comment might be: “Is 2/487 conversions a good conversion rate? It seems like a low one to me.”

You are right, I am sorry. I was commenting drunk on the subway. So is that a good conversion rate?

is sales really that hard for people?

you just talk to people and convince them lol its not that hard. i didn't know i was good at sales turns out i just have to be me and people like what i gotta say

It’s impossible if you’re scared of rejection, which an overwhelming amount of people are

hm i guess i'm weird then because idgaf about rejection as long as I have it my all

Yeah. Plus genuinely waiting to help oc

I always thought selling a good product is easy.

Creating a good product that is hard.

And selling a bad product is hard so the people with this skill makes a lot of money.

Creating a good product requires lots of interaction with your target customers. You can call the "sales" in the beginning, but it's really understanding how to tweak your product from an idea to solve a problem into something that fits into the customer's workflows and solves their problems. The only way to really validate the product is to see who pays money for it.

It's possible that you have natural charisma or talent. But I'd say the people on HN probably lean towards more introverted so sales is probably quite hard for them

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