Podcast: Remote Work, and Building Fast Teams

In this podcast, we cover:

1. What it might look like to create a system that streamlines back-office needs in HR, finance, and legal liberating operating executives to focus on higher-level responsibilities
2. Our view on remote work, and how we've gotten it to work for us at AbstractOps
3. Our thoughts on the transformative impact of AI on fundamental assumptsion of business operations
4. Critical cultural attributes that might set up an early-stage startup for success

Highlights

The origin story of AbstractOps

I was spending at least two thirds of my time on high priority things: recruiting, partnerships, business development, and product strategy. But I was spending the other third of my time on back office admin.

[...]

The fact that this information lived in dozens of systems (or in no systems at all!) drove me crazy. So really, we built AbstractOps to create a system of record for the backbone of a company – in the sense of HR, finance, and legal – and to connect the critical data objects that help a company exist and operate.

Why work on making companies more efficient?

I think there are only four or five industries, or ways of working, that really move the needle for the world: government, education, healthcare, financial services... and more broadly, as a horizontal layer, corporations. If you can fundamentally make a company more effective by changing how it works, and more than anything else reduce latency, then you can change how the world works.

[...]

What's hard about remote work?

I think it's the ability to create serendipity, which goes hand-in-hand with trust and bonding. I do think there are ways to mitigate it, like by having deep, one-on-one conversations and going through hard times together. Ironically, we've gotten a lot closer in the last six to nine months because the market is way harder and you feel united by the common enemy of time and money, in this market. The other thing that helps is having a smaller, tight-knit team that works in closer units. It's because of the two-pizza concept, which Jeff Bezos coined.

[...]

What separates a good team from a great team?

Curiosity. Everything else stems from that. If you approach every conversation from a spirit of curiosity, then you don't assume negative things about people. You try to understand why they do what they do.

[...]

Is it possible to systematize curiosity in a remote context?

I think psychological safety is critical. It's something I've actually had to learn quite a bit about, and is an area where I've had to grow as a leader. I have really strong opinions. But I've come to realize that people react strongly to anything a CEO says. I didn't think my voice was any different from anyone else's voice, or from when I was a COO... but it is.

[...]

What's unique about your remote team's approach to transparency?

1. DRIs make decisions – not managers or executives (which means DRIs need to have a high degree of visibility & context).
2. Our calendars are open.
3. Almost all of our Slack channels are open (except exec team + HR topics).
4. Compensation is open.

It's funny, because pay transparency is becoming more of a thing. We've actually listed base and equity for every role we have ever published, and we began doing that three and a half years ago. People don't have to wonder: am I getting paid fairly? They are, by definition.

What's going to be new about the future of work?

If you look at some of the most successful companies out there – Apple, Google, and Facebook – you'll see that their revenue per employee reaches a ceiling of around $1.5 million to $2 million per employee. That ceiling hasn't been broken yet, but I think we're going to start seeing it broken a lot more in the coming years.

Which then poses the question: is there any reason you can't be doing $10 million per employee in revenue, or in gross profit? And then, if you reach that milestone, what does that mean for the design of your company?

I think one aspect which will be key for this is leveraging agencies and contractors a lot. Because of remote work, this model has exploded.

We do this a lot. We have an in-house engineering team that sets the direction and strategy, vets the tools we use, ensures the specs are well written, and orchestrates the work being done... but then the flex capacity comes from an external agency. We use a terrific agency out of Eastern Europe. Same with other functions – we have an outsourced SDR team, and a fractional outsourced design team. So three of our core functions – sales, engineering, design – are at least partially contracted out.

[...]

What do you wish you'd done differently?

One: humility goes a long way. It's really important to balance low-ego and low-insecurity when you're the CEO.

[...]

Two: Realize your opportunity cost. "If this company were taken away from you today, and you had no obligations anymore, what would you do?" I would do the same thing over again, but just do it better this time around. So if that's your answer, then keep working on what you're doing. Otherwise... then maybe it's time to shut down your company and cut your losses. Life is too short.

[...]

Three: Instead of trying to solve too many general problems, try to solve fewer, more acute problems. The biggest mistake we made was trying to build this whole operating system for how companies work, and as a result, nobody knew what the hell we did. The moment things actually started working for us was when we could describe what we did with two or three words, like: "payroll tax compliance", and "compensation planning". These were very acute things that people could latch onto. They could point to them and say, "I need that!" as opposed to looking at an operating system for a company and saying, "what the hell is that?" It's really important that you can describe your company in two to three words.