Masterclass on Remote Work: Hiring, recruiting, and essential tools (Part 1 of 2)

This is the first part of a two part masterclass on remote work, now live here:

01:46 Meet Shogun, the e-commerce page builder 
02:58 They started fully remote as a side project that became profitable 
04:23 The Tools: Hardware and software that enables remote work 
07:40 How to do learning & development 
08:29 On recruiting for remote teams 
11:35 Remote recruiting process 
19:43 How to legally hire remote candidates 
22:05 Onboarding remote employees

Watch the full video at YouTube here: — You can also read the full Shogun Remote Work guide at their blog here

I guess we're all working remotely right now, so who better to sit down with than a team that is the best at remote work that I've ever seen, Shogun?

Today's a master class in how to run remote work teams, from a team that has been working remotely from nearly the beginning. They've gone on to create one of the best products in the whole portfolio, and they did it through great recruiting, great management, great software, and great processes.

In this masterclass today, they sit down with Katelin Holloway Partner at Initialized and former head of people at Reddit to walk through all of the secrets they learned the hard way so you don't have to. Part one is about recruiting, tools, workflow— Let's get started.

Katelin:  Hi, I'm Katelin Holloway. I'm a partner here at Initialized Capital. 

Joining me today are the co-founders of Shogun, Nick and Finbarr. Today, we're going to be talking about some of the best practices for working at home. And so as we all have been thrust into this new world of working, parenting, teaching and trying to live at home, all under one roof, we did what we know how to do best. So, here we are with Shogun. 

I'd like to take a moment to ask Nick and Finbarr to give us a little bit of your story.

Nick: So, we make software for the future of online stores. 

We've got two products. The first one, Shogun page builder — We're pretty well known for that. We have over 12,000 paying clients. It's a really powerful drag and drop page builder, but it's seamlessly integrated into e-commerce platforms like Shopify, BigCommerce, Magento, and Salesforce Commerce Cloud. 

Our second product, Shogun Frontend — it's a part of this movement kind of referred to as headless commerce, where basically, it takes over the entire frontend of the technology stack. The part that all the shoppers can see, when they visit the site. And so what it is, it's a really powerful experience management and content management software, that renders the frontend as a progressive web application. The benefit to that, is its sub second, so it's literally like the fastest websites that you've seen on the internet. It loads literally instantly. So that's the second product that we've been working on.

Finbarr: So hey, I'm Finbarr, CEO and co-founder of Shogun, so we've been fully remote, since October 2015. Which was about six months into when we started. We've been remote, for the better part of five years now. Originally we went remote because, my co-founder Nick here, moved to Thailand, and I was still in San Mateo, California, which is where I'm based. And so we were removed from each other. 

I was working for Y Combinator as a software engineer, Nick was doing some consulting with some VC folks out in Thailand. 

Shogun was a part-time project, that was growing every month and generating some revenue. And it got to the point where it was generating enough revenue that we could hire some contractors to help us, purely out of the revenue of the business. And so we started looking for extra team members. 

Of course we went online to Upwork, and started looking for some part time contractors to help. It turns out that you can find absolutely amazing people all around the world on platforms like Upwork. Because Nick and I were already remote from each other- we had a big timezone difference, it wasn't a big stretch to add another person who was also fully remote. So that's kind of how we got started on the remote path. And we've continued on that ever since.

Hardware and software: The tools that enable remote work

Katelin: So let's talk about tools, home set up, the gear needed, just to actually physically work remotely.

Nick: A really high quality camera, usually a high quality external mic is a good investment, monitor, speakers, mouse, keyboard, and something to hold your laptop. 

In terms of software, there's a quite a bit. Slack, which is for general communications, and stuff that can be slightly ephemeral, right, it changes quite quickly. In addition to that, we use Notion, as our internal wiki, that's more permanent knowledge lives. And then obviously Zoom, what we're using right now is great for synchronous communication. 

We try to have a lot of our communication be default asynchronous over Slack, and in Notion, but obviously it's really important to hop on calls when you need to communicate in real time.

Finbarr: Yes, so actually, one thing I want to add to the hardware tool list is, a really comfortable chair. I have an Herman Miller Aeron chair, which is super, super comfortable. It's essential to have a chair that's sort of comfortable. 

Standing desks are also super handy. I have this like adjustable, motorized standing desk that you can see in the video here, make sure you're comfortable. 

In terms of software, we use various project management software like Clubhouse, for engineering project management, but the main one really, Nick touched on Slack is kind of almost like our remote office. That's where we're hanging out constantly. And you can typically find whether somebody is online or not, and Slack, we have no expectation of working hours or when people are online are not, it's quite flexible. 

Then folks are using different tools for their specific functions. So, our design team is looking at Figma. They're using InVision for prototypes right now and Sketch. Our marketing team is using various SEO tracking tools, like SEMrush and this kind of stuff.

Nick: A couple of the other tools like obviously, you have your core tenants that are covered by by Slack, and Notion, Gmail and Zoom, right? Those are kind of the ones that are just the pillars for technology for remote. 

There's a whole bunch of other technologies that I actually think are really useful. I love CloudApp, where you can really easily like annotate a screen shot, or make a GIF, or record a super short video. It's perfect for that intermediary where it's not quite something that you can just do written, but it's not quite worth getting on a call for, but you need to describe it visually. I think CloudApp's like perfect for that. 

Learning & development while remote

I also think that learning and development and knowledge transfer is really important. Obviously, some of that is conveyed like Notion in the wiki. But we recently started using learning development software 360Learning. I also checked out Lessonly a little bit, and still kind of reviewing, we're still kind of considering both of those vendors, but basically—how do you scale your knowledge? 

And what you can do, I found was I use like, you can use CloudApp, I actually like Loom a little better for video recording, so I'd record a video of myself, demoing a product, or giving like kind of like how I pitch the new product, something like that. Take that video, run it through, Rev transcribes the whole thing. 

So now I've got a video, and basically is what's like a blog post, right? Then from there, our operations team takes that, and inside that learning development software, turns that post of my words into quizzes, that are fill in the blank, true or false, all this or that, and then our team members run through those programs, so it's creating knowledge at scale.

Finbarr: The only other thing I'd mention would be Geekbot, which is awesome.

Recruiting for remote work

Katelin: Let's talk about recruiting. So, because you have been operating remotely for so long, how difficult have you found it to actually recruit, inviting people into a remote team, does that have as its advantages or disadvantages?

Nick: I would say that it mostly has advantages in our experience. When we initially started, and really I should probably let Finbarr talk about this, but, it was basically we went on to Upwork and kind of dialed the controls up to the maximum. And we were quite surprised with the level of talent that we found doing that. And so what I mean by that is going in, looking for people that have exceptionally high ratings, have worked significant volumes of hours, have succeeded at the core level of tasks that Upwork provides. 

And when you max out all of those controls for all the premier stuff, you're left with relatively few results, and those results happen to be very good freelancers that are available. It's also, a really good way to initially engage, because you're going to be obviously setting up an agreement via Upwork, which makes things a little easier paperwork wise. And so, that's where we initially started. Was in that manner, and would recommend that to companies.

Finbarr: Hiring remote for us has been a tremendous advantage. When you hire outside of just one locale, the talent pool is much, much larger. And so you're getting applications from people all over the world. 

One of my favorite things about working on Shogun is, just the diversity of the people. The people in so many different backgrounds and so many different walks of life, in so many different countries. 

Now we work with people in 21 different countries on six continents. And so just getting that exposure to so many different perspectives is amazing. In terms of, you know, finding people, we found it fairly straightforward honestly. 

There are a number of websites that we've used to find people, we post on WeWork Remotely, we post on Hacker News Who's Hiring, we have a profile on AngelList, we've had some really amazing people apply through AngelList. We've posted on Y Combinator's Work at a Startup portal, and also written some software to scrape that and find really good candidates there, which has been super helpful. But in our experience, every time, pretty much every time we've posted a job, we're inundated with really high quality applicants. And the problem is not finding people. It's picking which one is going to be the right one for the job- because in so many cases, we've had a lot of very highly qualified people apply.

How to run a remote recruiting process

Katelin: That's amazing. So your top of funnel sounds like it's very, very healthy and very diverse, because of the opportunity to work remotely, which is incredible. Can you walk us through as you get further down the funnel, what your recruiting process actually looks like?

Nick: Usually the process is as such: You've got a screening call, and that's basically to just suss out general things. And also make sure that it's a good fit right off the bat, both in terms of career growth, and what's going to make them happy, in terms of compensation. And we'll actually go on a slight tangent there. 

One thing to note is that, when we're hiring globally, sometimes there's this tendency for people to think: "Oh, well, you know, I'm going to pay very, very little for x or y role." It actually doesn't work like that, you still get what you pay for, right? I would say while there's maybe deflation in some countries, there is inflation in perhaps some main cities in the United States, that start with San, and end with Francisco, but, you know, maybe I shouldn't said that. 

You'll find that you still get what you pay for. So you need to be going out with competitive rates to find quality talent. We start with a screening call, and then from there, we suss out general requirements and whether it's going to be a good fit. From there, generally, it's brought to team members that would be working, with that individual. And then it progresses to whoever the hiring manager is, and then the co-founders. We try to run a relatively quick cycle, we don't like things to be like drawn out. So we'll move quite quickly and rapidly, that's one of the advantages of being a startup. 

Work together with candidates before you hire them using paid trials

One thing that we're really big on is, wherever we can, we'll engage in a paid trial, or a paid test of some kind. For engineers, this is rather straightforward. We'll basically just ask what their desired hourly or day rate is, and we'll put them on a modular project for them to work on. That kind of doesn't require being highly integrated with the rest of the team. 

For potential designer, it might look like: design one screen if we're hiring for a UI designer, visual designer, design one screen really perfectly, and then mock up the flows around that screen and tell us about that interaction. And we'll give a real live use case in our software. But again, this is a paid design test. And we're very upfront and very clear about that, and we generally agree to whatever that individuals specified rates are. 

Obviously for some roles it's easier, right? Like engineering, design, support. It can be really hard or almost impossible for some business side roles, like BD or sales. So for those, we try to, again, not just have interviews that are just asking questions and talking, but try to make them more interactive. So for BD, we'll do a demo. And we'll say it matters a little less about you knowing our software perfectly and more about presentation, setting up the meeting, setting the agenda, talking about the software, asking discovery questions and stuff like that, and walking us through maybe one core flow. 

These are all examples. But it's really, really important to actually have that action part of the interview and screening process where they're doing something functional.

Katelin: I would say that that's a fairly unique approach to hiring and the recruiting process. I think that in a standard workplace where you have at least one primary office, you typically would spend funds to fly a candidate in if they are remote, bring a candidate on site. And typically there's a homework component. That's something that we've seen more and more in recent years where candidates are sent home, to then produce something and bring back or take a test. So what you're saying is that instead of doing that, you have this cost savings from not flying people to you. And then you can convert that into actual wages for time spent, which I think is very, very pro candidate, very pro employee.

Check references

Nick: We used a contractor agreement for that as well and just do an hourly or day rate. A very important other thing is, we also do reference checking, rather extensively, and generally before like a final conversation, like with Finbarr. And so we'll ask for their references. But generally people will give you the references that they think are going to speak best. So we'll also take a look at their LinkedIn profile. And then after they've given us the references, we might ask for, "oh, hey, could you actually give us a reference at this company, or that company," they might not have listed. And we'll actually follow up with all of those references. And then we have a call template for all of those references, and kind of asking very specific questions, about the individual and their performance.

Onboarding actually starts at interview stage: Be careful not to waste a candidate's time

Finbarr: I truly think that, team member onboarding, really begins at the interview stage, and so you have to give people, in fact not interview, the application stage. You have to give people a great experience, right from the beginning. And so we really don't like to waste people's time. If people are going to be spending time, working on projects for us, we are absolutely going to be paying them for it. I'm not a huge fan of the unpaid assignment, that's only going to take two days, or two hours or however long. So we just don't do that. 

I think that leaves a really good impression on people. The trials, enable us to figure out what it's actually like to work with people. You know, when you switch jobs as an employee, you don't really know what it's going to be like to work somewhere until you actually do. And the same is true, as an employer, you don't really know what it's going to be like to work with somebody until you actually do. So, I think that it's a great opportunity for both sides, to make sure it's a mutual fit.

We're very open with people about the fact that that's why we do this. So that we can determine what it's really like to work together. It cuts through a lot of the noise and interviews and just get straight to the signal of, can this person actually do the job and what is it like to work with?

Katelin: I think that's a pretty high integrity approach to both considering the employee experience, which I agree absolutely starts with the candidate experience, and then hopefully evolves into the employee experience, but it's also compliant. You know especially when you're thinking about remote work, and you have people working in different parts of the world, really, you know, some countries will allow for a probationary period, but if you know, we're here in San Francisco, for example, we are at will employers, so there is no trial period that we can do. So I think that that's a really interesting and unique approach to really engaging in a very authentic way.

Pro tip: Ask "What makes you happy in terms of your compensation?"

Nick: One thing I was going to say, speaking of kind of unique approaches, I've heard that people are kind of surprised by this or find this interesting. In our screening interview, we ask this question, which is, what makes you happy in terms of your compensation? And that's the exact phrasing we use. And... some people, a lot of people will tell you exactly what they want. Some people will hesitate, they start to feel like it's a negotiation. The funny thing is, it's that, it's actually where you know, where you kind of give them, you know, hey, this isn't a negotiation or anything, we just want to make sure, that our offer's going to be aligned and that we're going to be able to make you happy. And that ends up, whatever they end up stating in that, or higher ends up becoming their offer. We really believe in compensating people in a way that yeah, that really, really makes them happy. Being aligned on compensation and making a person really happy is very important.

Katelin: Those questions should absolutely be behind every great compensation, philosophy and framework. So understanding that early and upfront, before it becomes the negotiation, or before it gets to the point where you're actually putting pen to paper for an offer letter, is absolutely unique. That's what's really cool. 

Legally hiring and onboarding overseas remote workers

So let's say that you've identified somebody now through this process, you've done a project with them, a paid project with them, and you're like, great, I think this person is going to make a phenomenal team member, to come and join the Shogun team, what does that process look like? What does the conversion process look like?

Pro tip: Get a great lawyer

Finbarr: This is an area where you need to be really careful. And I certainly recommend engaging with some very competent lawyers, that understand the complexities of international compliance. Something that we've spent a lot of time and effort on, and we continue to invest in. But the answer is, it depends. It depends where the person is, and kind of it depends on how you want to engage with them. You know, it can vary from, let's start with a contract trial, or, you know, a kind of midterm contract, to, we're going to set financing in your country, and this is how we're going to do that, this is how long we're going to take, and you really just need to take good legal advice on that and figure out the appropriate strategy.

Katelin: And I agree, investing in those partners that you have from a legal compliance, HR, and finance side of the house, will become critical components to your ability to operate remotely.

Nick: I would add that, if you're working domestically within the US, but remote across the US, looking into professional employment organizations, can help solve a lot of the headaches. In addition to that, you can go and find some of these services that'll help you do all your filing with various, you know, state level secretaries, state things of that nature. There's like a, you know, Wolters Kluwer incorp services, CSC, eMinutes, there's a whole bunch of these providers, 'cause you obviously want compliance both at the employment level, and then also at the state filing level. So there's lots of different factors to consider. But there are that we could probably have a very deep discussion about that. And then obviously setting up subsidiaries in additional countries that you operate in, is something that you would certainly want to seek out legal counsel for, which is what we do at Shogun.

[Editor's note: Garry recommends the payroll/HR service Rippling for a lot of the PEO work you might need in the United States.]

Onboarding remote employees: Getting people up to speed

Katelin: Walk me through your onboarding process. How do you ensure that, new team members are connected to the right communication tools that you walked us through earlier, they're connected to the right cross functional team members, and really begin to experience the culture of Shogun?

Nick: That initial step is actually somewhat automated by this really awesome tool called Donut, that is seamlessly integrated into Slack. You can set it up, so that you have this automated bot in Slack, that goes and conveys information, creates all checklists, and sets up little meetings, you know, between people, and it's a super helpful tool. I definitely recommend checking it out.

Using Donut for onboarding automation: get feedback and track NPS for new recruits

Finbarr: We always try to have a good amount of clarity for people on what's expected from them on their first day, their first 30 days. Some of that information is conveyed with Donut and others. 

You can basically set up sequences. It's like a playbook of interactions that you can start with Donut so, it might message their manager and say, "hey, reminder, this person starts today, "so set up a call with them." And it can even automatically show you calendar there those who soon to review so you can, easily schedule meetings and everything. So we really do automate a lot of the onboarding process, is something that we've invested in very heavily. 

We recently have scaled up an operations team internally, where a large part of the focus of that team, is on team members satisfaction, team member onboarding experience, learning and development opportunities, career progressions, and that kind of thing. But they kind of maintain those playbooks for onboarding for all the different roles, and they work with the hiring managers to make sure the onboarding are smooth. And we also, have a kind of NPS component of the onboarding where people are asked after 30 days, "how was that for you?" "What can be improved about that?" So while it's still really fresh in people's minds, and then we use that to iterate on the onboarding process. But typically our first first day, will involve joining. 

So usually on a Monday, it'll be joining a team meeting, we try and keep meetings to a minimum, but Monday is typically our day when each person will meet with their team. So on the first day, they would join with their team, and probably have calls with some of the other team members. And then over the course of that week, it would be more calls, having an understanding of what we expect from them in terms of deliverables, and just working very closely with their kind of mentor, within the company. Might be their manager, or might be somebody else on the team.

Thanks for reading this. As always you can watch the full video on YouTube.

Learn more about Shogun at

You can follow Katelin, Finbarr and Nick here: @katelin_cruse, @finbarr, @nickraushenbush

You can also read the full Shogun Remote Work guide at their blog here.