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It’s Not Just Technical Debt; Everything Gets Painful & Slow as You Scale

A tremendous amount gets written about technical debt (definition) in the startup ecosystem. As you scale your product and engineering, you inevitably make sacrifices for the sake of speed that lead to pain down the road. What startups (and people who interact with them) don’t often realize is that this same problem happens across nearly every team and every form of business practice.

Let’s start with a story to illustrate.

Heaton sees a job posting on the SEOmoz site that looks like a perfect match for his skills. He applies for the position through the company’s Jobvite form and 4 days later, gets an email asking to chat on the phone. The hiring manager loves Heaton and tells him via email 2 days later that they’d like to have him in for a full loop with the team. 10 days later, Heaton comes in for a full interview round and meets 4 of the 6 teammates he’d be working with. The other two are out, so Heaton schedules 3 days later to come back in and meet with them. He does so, and 3 days later, gets a written offer for the position.

Sadly, Heaton had interviewed the day after he applied for the SEOmoz position at Bigevilco, Inc and they sent him an exploding job offer with 3 weeks to consider (relatively generous and plenty of time, he thought). On the last day, Heaton accepted, 1 day prior to the offer from SEOmoz. Heaton’s upset, having preferred to work at a startup, but he figures if SEOmoz takes 23 days to get back to an interviewee for a supposedly important position, their communication and priorities are probably too messed up anyway.

Here’s the reality:

The hiring manager is also the product, project, people, and technical manager for the 6-person team onto which she’s trying to hire Heaton. They’re hiring because they’ve got huge amounts of pain on an issue that’s causing sleepless nights and overwhelming days. There’s no HR or hiring-specific function in the company, but they’ve got the go-ahead from the CEO to make the hire, so they’re adding it to an already rough roadmap. Many folks on the team have never interviewed or hired before, and some may not realize how relatively critical it is to be fast with responses on the hire vs. fast with fixing the existing problems. Likewise, to each individual, it feels like they’re only taking a couple days to get their replies back, but it’s the combination of many 24-or-48-hours-before-an-email-reply that leads to Heaton’s bad experience.

It’s only after losing Heaton to Bigevilco, Inc that the team huddles up and tries to figure out how to solve for this problem next time. And even then, they might fail depending on the severity of issues they’re facing and who’s on that team that recalls the Heaton debacle.

Problems like technical debt happen in HR, in partner/vendor relationships, in marketing channel investments, in product spec process, in team happiness investments, in office furniture – pretty much anywhere and everywhere a startup can take shortcuts and ignore a pain point, they will. The simple visual below shows what I’ve seen time and again both inside SEOmoz and from dozens of others:

It’s not every problem that goes unaddressed or that scales poorly, but it’s enough to create an inflection point that, by and large, seems to always happen right after you’ve raised money.

The day our series B round closed, Brad called me on my cellphone while I was in the office. Given that Brad hates the phone (a great quality I need to write about at some point), I answered immediately and remember the conversation better than I usually would.

Brad: Don’t worry about the next few months. It’s going to be rough for a bit as you pay off all the startup debt you’ve accumulated.

Rand: OK… Wait… What’s that?

Brad: All the shortcuts you’ve taken to get to here without investment are going to suddenly seem to come bite you in the ass. That’s normal. It happens to all the startups we invest in. You’ll have things you need to buy and people you need to hire and stuff you need to get done and all of it will take longer than you think and you won’t be able to run as lean or as fast as you want. But, you’ll get through it and come out the other side better and more stable for it.

Rand: OK. That’s good advice. We’ll watch for that.

This is probably the point where Brad thinks to himself “poor kid, he has no idea.”

I can say that after the past 4 months, I have some idea, and I’m probably going to have a much better idea in another 4. Brad knew what he was talking about. On every team and for nearly every function, there have been pain points of going back to the architectural or structural level of how we did something and fixing or upgrading it, with far less customer-facing value than you’d hope for. As an example, we hired a full time recruiter, then just last week, a full time recruiting assistant, precisely to avoid situations like what I described with Heaton above (not a real example, BTW). Prior to that, we made a bunch of investments in data retrieval backups that we thought would carry us for at least a year or two – nope – they barely lasted two months before we had to start acquiring more (and that’s just to serve existing customers).

My two recommendations:

  1. If you’re at a startup or starting/joining one, be ready for this type of pain. It’s tough to do maintenance work on a moving vehicle, but that’s exactly what you’re in for.
  2. If you’re interacting with a startup from the outside, empathize with their pain and anticipate that as a vendor or partner or a candidate, they may not be broken or evil or communication-challenged so much as they are experiencing startup debt.

If I discover good ways to pay off debt faster or more efficiently, I’ll try to write about it here, and if you’ve got advice for getting through these challenges, I’d love to hear about it.