My first year in sales as technical founder

> 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".

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!

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

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

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)

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.

"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.

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.

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”

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

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.