Adii Pienaar - Receiptful

Adii Pienaar is an author and serial entrepreneur. His current company, Receiptful, a service for generating email receipts and up-sells, is his second fully distributed team. (The other, WooThemes, was just sold to Automattic.)

Adii talked to Pajamas about building a remote team at Receiptful, keeping everyone connected, the reality of balance, and how the first time around has influenced his second turn as an entrepreneur.

What does Receiptful do and what do you do there?

Today, Receiptful is an API that lets you send beautiful e-mail receipts that increase customers' lifetime value through the use of targeted, personalized marketing messages / up-sells. It also integrates out-of-box with leading eCommerce platforms to replace the default, dull and generic receipts of those platforms.

We are however moving towards an intelligent and automated marketing solution for eCommerce merchants with the new, complimentary tools that we're building.

I'm the founder & non-technical guy at Receiptful, which means I do everything that no one else wants to do. Seriously though, it's my job to build the team, align our ideas & vision and remove friction from all of the processes & projects.

Your last company, WooThemes, was also remote. What draws you to distributed teams and made you want to do it again?

I think part of this consideration is just the result of another decision: my decision to live in Cape Town, South Africa. I'm born & bred here, so building a global company from here requires me to work with people all over the world. In that sense it would also not be viable to try establish physical offices everywhere.

Beyond that though, I'm a big believer in personal freedom and I believe working remotely (partly) enables that. I don't want to be bound to one location, one work routine or a rigid holiday policy; instead I want to work and play hard when the mood hits. I also want this exact same freedom for everyone with whom I work.

How many people are at Receiptful now and how many different timezones do you cover?

We're seven team members right now and six of us (soon: all seven) are based within a hour or two of each other (across Cape Town and various European cities). The outlier is currently based in Argentina.

This has made sense initially, because it's been easier to work more in real-time more frequently, which I think is very beneficial in an early-stage startup. As the team grows though and we expand to multiple timezones, asynchronous collaboration also becomes easier and it's not that important to work in real-time as often.

How do you keep everyone feeling connected?

Like all other startups, we spend a lot of time on Slack, where we both work and just hang out.

Coupled with that, we recently had our first team retreat which was an important experience for us to build relationships.

I don't want to be bound to one location, one work routine or a rigid holiday policy; instead I want to work and play hard when the mood hits. I also want this exact same freedom for everyone with whom I work.

What are the biggest challenges you face with a distributed team and how do you overcome them?

I think the biggest challenge is not having the context of tone and body language in communications. In that sense, it is sometimes easy to misread what someone else said and the challenge is not to react on that. That's why getting to know team members in real life is so important; you get the opportunity to understand their quirks and the way they communicate.

What is the biggest benefit that working remotely has afforded your company?

As a starting point, we've avoided the cost of an office. And on top of that, I'm able to build the best team I can without limiting myself to a specific skills pool in a specific geography.

That said though, I think the personal perspective is much more important here. I'd like to believe that I'm not just an employer or manager, but that I also help with life coaching / development. As arbitrary as that sounds, I think it's important to enable individuals to be whoever they want to be and working remotely is a big part of that freedom. So over time, I believe this environment should encourage that self discovery and development.

Since Receiptful isn't your first rodeo, what are some of the lessons you learned building a distributed team at WooThemes that you've been able to carry over?

I think the key is to only hire people that will fit your culture.

For me with Receiptful, I essentially targeted individuals with two types of character traits:

  1. A thirst for learning; and
  2. A love for a challenge.

I think working remotely and working on a startup requires both of these character traits. They also align with my own personality, which means that there's alignment with the collaborative culture that we end up creating.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Proactive and honest communication. Nothing beats this.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

I like checking in with team members in a one-on-one way often and I ensure that I work with each of them on something often. This more intimate collaboration normally gives me the cues as to whether an individual is finding something challenging.

Beyond that though, I've encouraged my team to proactively communicate with me about anything without ever fearing a backlash. In that sense, I try not be the boss, but just be one of the team.

What sort of culture does your company have?

It would probably be easier to share some of our stated values with you, but somehow I don't think that this is our culture. Instead our culture is what's happening within the team right now.

So I'd say we have a light-hearted approach to life and work, but we're ruthlessly customer-centric and ambitious in terms of how we craft products that create value for our customers.

How do you handle hiring on a remote team? Is your process for vetting prospective employees different, do you think, than if you were hiring for an in-office role?

Nope - it's not different at all. The only benefit I'd have if I hired an in-office team member eventually would be the context of their tone and body language in their communication.

My hiring process looks like this:

Describe your personal work environment.

I work from home in the countryside (about a hour's drive outside of Cape Town city center). My wife and I have have two young boys, 3.5 years & 6 months old, which makes this challenging at times, but also super-rewarding. I'm lucky enough to have a separate study where I have a desk and some storage for gadgets, but beyond that it's not really sophisticated.

I've found that the more I don't isolate the different parts of my life, the more integrated and balanced I feel.

The only other important thing is that the kitchen is a couple of metre's walk to grab a fresh coffee.

You wrote recently that you don't think work/life balance exists and have instead adopted a more "liquid, flexible and integrated approach." Can you explain what you mean by that?

If you're striving for work and life balance, you're essentially saying you're trying to consolidate two isolated poles in your life. My experience has just been that such a consolidation process has far too much friction, which means you're always falling short.

So what I do now is to be more liquid about this where life is just life. The best example I have of this is when Adii Jr comes home from pre-school at lunchtime. Sometimes he catches me amid an intense session of work, where I'm in-the-zone and being super-productive. Other times, I'm making a coffee and I'm not even at my desk. Regardless of my state of mind though; he always has the same aim when he gets back home: he wants to spend time with his dad.

There's thus no binary way to switch off work and switch on life in that sense. So I just go with the flow, which normally means it's just one big mushy mixture called life.

The key for me has been to remove the friction and pain involved in these transitions. I've found that the more I don't isolate the different parts of my life, the more integrated and balanced I feel.

How do you keep distractions to a minimum? How do you measure efficiency on a personal level?

Physically I work in a separate room in the house and my family understands that I prefer not to be distracted when I am working. As such, I also minimize the amount of time I work elsewhere in the house. Mentally I've learnt to accept distractions in my stride and not fuss about them too much.

I always feel like I can be doing more. But I do believe that I'm massively efficient when I do, do things and I have a good sense of knowing when I'm not focused and not producing work to my normal level of efficiency.

What are some of the tools you couldn't live without as a remote company?

I'd say the only thing that would make our life really hard if we didn't have it today is Slack.

What advice would you give to a company heading down the remote working path?

There's no halfway measure; you have to be fully committed to this. It also requires a whole paradigm shift in the way you'd like to build and manage your team; so it's not just a case of hiring remote team members without also changing the way your company works right now.

Josh Catone
Josh has been the Content & Community Manager at feedly, the Executive Director of Editorial Projects at Mashable, the Lead Writer at ReadWrite, and the Lead Blogger at SitePoint.