Three lessons from selling to developers
Jack once took a hopeless sales lead out for sushi at his own expense, purely because it felt good to build the relationship. Three years later at Stack Overflow, he still counts it as one of the clearest lessons in why qualifying leads matters more than chasing the ones that feel nice.
This is a solo essay episode. Jack shares what he learned working as a sales development rep at Stack Overflow, on the early team selling Stack Overflow for Teams — an internal, login-gated version of Stack Overflow for a single company.
It's a monologue rather than an interview, built around three lessons: why inbound leads are so much easier than outbound to developers, why qualifying leads early saves months of wasted effort, and why the entire game comes down to finding a genuine champion inside the buying organization.
The Q&A below is experimental — extracted from the episode transcript with AI. If you spot a mistake, let us know at jack@scalingdevtools.com.
What was the actual job, and how did leads come in?
Jack was a sales development rep, responsible for booking meetings — paid a bonus for each meeting booked, another if it progressed to a certain funnel stage, and a small percentage if the deal closed, though nothing like a closer's cut. Leads came either as inbound, someone signing up for a demo on Stack Overflow's website and getting allocated out to the team, or, far more often, as outbound: cold emailing, cold calling, conferences, cold LinkedIn messaging, and Twitter. As one of the first people on the team, a lot of process simply wasn't in place yet, and despite Stack Overflow being a huge company with around 50 million monthly developers at the time, very few leads were actually coming in through marketing.
Why are inbound leads such a big deal, and why is outbound to developers so hard?
When a salesperson gets an inbound lead from a good company, it's a genuinely euphoric moment — you're about to set up a call and get paid, and inbound converts at a much higher rate than outbound ever does. Outbound to developers, by contrast, is extremely difficult. Jack has worked as a developer himself and almost never checked email, because nobody emails developers — everything happens on Slack. Cold emails barely get opened, and developers are deeply skeptical of anything that smells like a sales pitch. LinkedIn doesn't help much either, since developers tend not to use it heavily and are wary of being mistaken for recruiter bait. Stack Overflow's policy, and Jack's own preference, ruled out spam outright, so every email had to be genuinely tailored to the person — and even then, response rates stayed painfully low. Researching someone, feeling like you're getting to know them, sending a considered email, and then just getting ignored, all day, every day, is genuinely hard work.
When did outbound actually work?
The clearest successes came from finding someone who already cared deeply about the exact problem being solved. One example: a person at a large European company had already written articles arguing that internal knowledge-sharing was broken and that companies needed their own internal version of Stack Overflow. Jack sent a long email, against the usual advice to keep cold outreach short, explaining specifically why he agreed with the article and how the product related to it — and the person was thrilled to receive it, because he was helping them achieve something they already wanted, now with the weight of Stack Overflow behind it. That deal became one of the biggest of the year. The broader lesson: a cold email is unlikely to persuade someone to rethink their entire worldview from scratch, but if someone has already demonstrated they care about a problem and has tried to solve it themselves, showing that you also care about it is a genuine way to connect — and at that point your incentives are naturally aligned, so it barely matters that you're technically a salesperson reaching out.
What's the lesson about qualifying leads?
It's a cliché, but don't waste time on people who are never going to buy. Jack once took someone out for sushi at his own expense, building a real relationship with a genuinely nice guy he got on well with — but the company was on the verge of laying off half its team, and there was never any realistic chance it would buy. In hindsight, that pursuit was more about his own ego, or the good feeling of the relationship, than any real read on the deal's prospects. These enterprise deals can take two years to close, requiring a real swell of internal momentum, so they shouldn't be undertaken lightly — and that experience taught him to qualify leads honestly rather than following whichever one feels most pleasant to work.
What's the core lesson about champions?
Sales, in Jack's framing from Stack Overflow, comes down to champions. If you're selling to a founder, the dream scenario is someone who's genuinely passionate about the problem and has the power to just make the purchase happen — you barely need to help them, because they can implement it themselves. Selling into a big organization is different: you need someone whose personal job success is closely tied to what you do, who genuinely believes your company can help them, and then you need to help them as much as possible to actually close the deal. The first step is finding someone who truly cares; the second is helping them bring the deal home. If that person is, say, a Scrum master who's passionate about the tool but needs to get a VP of engineering on board, your job becomes helping them pitch that VP, get them engaged, and then figure out who else needs to sign off — budget owners, legal, whoever else is in the chain — and helping navigate all of it. A room full of people who all think it's a good idea, with no single person driving it home, will never actually close.
What's the summary?
Inbound leads are golden, and Jack doesn't think outbound is the right primary strategy for developer tools companies — developers don't like cold emails, and heavy investment in marketing that lets people discover and research things themselves tends to work better. Qualify people out early rather than getting emotionally invested in a deal that was never going to happen. And above all, focus relentlessly on finding the one champion who's genuinely aligned with solving the problem and wants the deal to happen — then do everything you can to help them get it done.