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Ask HN: What are the biggest challenges preventing startups from hiring remote?
176 points by hichamin 11 months ago | hide | past | web | favorite | 135 comments
We're starting a new company focused on solving the problem of talent war by helping late-stage startups have successful remote collaborations with tech talent. However, we're still trying to figure out which vertical to focus on. Which of these verticals is most pressing?

1. Sourcing & vetting candidates? 2. Managing international payroll? 3. Bootcamps? 4. Infrastructure & working space?

Let me know your thoughts!




Others have mentioned this to some extent, but what I've found the most challenging is when a company tries to do both local and remote, but was not remote-first. People who are remote are de-facto second-class citizens by virtue of the fact that they aren't included in hallway conversations or casual meetings. It's incredibly hard to overcome that. Teams that started remote-first are already well-practiced in inclusion and remote rapport-building, so it's less of an issue for them. But people who have the opportunity to meet locally and build rapport locally tend to get lazy and their remote muscles atrophy over time, unless they are making a very conscious effort, or the habits have already been deeply ingrained in them over time.

I'd add that this culture-setting rolls down from management -- if they aren't setting a good example, others will falter and the remote-supporting culture will fall apart.

Things like payroll, taxes, infrastructure are all solvable today, IMO, with the right resources or tools.


>I'd add that this culture-setting rolls down from management -- if they aren't setting a good example, others will falter and the remote-supporting culture will fall apart.

As someone who works at HQ for a local-first company with a significant contingent of remote workers in two satellite offices, it's _exhausting_ to be the developer in the corning who has to say "can we make sure the remote guys can hear OK" or "got a ping from Dan, remote guys aren't getting sound" in every single meeting.

Our office infra guy got a microphone with a padded box around it that you can toss around during the full company meetings so remote people can hear audience questions. The execs talking at these meetings have never once said "hey make sure we pass around the mic," it is always someone sending a text onto the big presentation hangout screen from a remote office saying "can you repeat the questions too please?" while the mic sits there on the little table right fucking next to the main speaker every single time.

When the managers and leadership don't care enough to prioritize it, it's almost impossible to change the culture around supporting remote team members.


But why should the local team all have to suffer and endure this hassle just so a few randos can enjoy their life being digital nomads? remote workers chose their bed, they knew the risks, they should deal with it.


Or, those employees are good, they are strong part of the company and with your life-threatening sacrifice you can... Pass the damn microphone around and get everyone included. Including people who are (not) digital nomads, live in the same city as yours but decided that growing up their kids rather than dropping them at childcare brings more value to society than the next meeting where a company care so much about you that they don't even bother passing around a microphone?


Ya I tend to think you need to run entirely remote, or entirely in offices. Or... you have your remote team running entire projects with an entirely sep organization, although that is hard and I am not aware of any organizations doing it well.

Biggest challenges?

Communications - I think every company has this problem but if you don't solve it when you are remote it will crush the company eventually. Whereas an office company can be shitty at communications and still do ok.

Execution... - LOL, I feel silly saying this but if your devs are split all over it is hard to collaborate, esp depending on speed and size. You need really great organization, focus, and just the right amount of meetings. You also need to do that in a way that gives them the ability to write code without checking in with someone every 10 min or stepping on toes. Esp if you are crossing big time zones, you have to really think and plan who is working on what, and it might even affect the entire design of the app...

quick background - grew a 100% company to ~135 people in 18 countries. Mix of software and dev ops and customer service.


My previous employer eventually decided to limit hiring to North American time zones so there's a good amount of working hours overlap between team members for actual synchronous collaboration. Without that, we've found it's really hard for a remote team to match to the level of productivity of a fully-in-office team.


Agreed. I've worked for a remote-first company, and another company where for a while I was the only remote employee. The difference has been tremendous.

I'm sure there are some special circumstances where being the only remote worker on a team works out ok, but my experience has been horrible.


As a remote worker my entire career, I can't more strongly emphasize this point. This is the biggest single factor between whether it works for a company or not. I'd argue it's even more important than hiring the best people. A remote first company with B engineers will likely be more effective than a company with A engineers that gets that wrong, especially at larger team sizes.


>Others have mentioned this to some extent, but what I've found the most challenging is when a company tries to do both local and remote, but was not remote-first.

I'm interested in this, as a person who does remote work, and has experienced some of these issues.

So, what are some good remote-first companies? I know of a few that may be: Automattic, Scrapinghub. What others? Asking all here, not just the parent commenter.

Maybe this should become a separate thread. Note: Obvious, but: "remote-first companies" is not necessarily the same as "companies that are hiring for remote positions".


Look into Jason Friend -- he literally wrote the book on remote work.

https://basecamp.com/books/remote

As for your actual question, I don't yet know of a great resource for understanding which companies are truly remote-first, but would love it if someone had one to share.


Thanks, I will.


The biggest challenge to making remote workers successful is the existing company culture. If the organization has not been built with a conscious "remote-first" mindset, new remote collaborators will inevitably be excluded from necessary communications and decisions. Making a remote worker a true part of the team requires a massive culture shift if your company does not already (successfully) do distributed work.


You also need to maintain the culture. A phenomenon I just went through is a company that started remote-first, then someone had the brilliant idea to get an office for this or that geographical cluster of people, and slowly but inexorably remote workers were marginalized.

Some people feel really insecure without an office, deep inside they think it isn't a "serious business" unless you own real estate in a "serious" postcode. I don't know if it's just an European thing but it's definitely an attitude I've encountered.


It also depends on the business somewhat, but actually having an office you can invite outsiders to (investors, prospective clients) can be an indicator of success. Truthful or not, it's the perception that counts.


I understand, but that's such an "old world" style. It's like building a datacentre, in the age of cloud computing, simply because owning big iron is an indicator of success (all the big boys have datacentres, right?).

In IT, tbh, I think we should just own it. There are more productive and creative ways to send out that sort of signal.


I'm jumping in to say that I agree with you. Our industry quite literally invented tools to make physical offices obsolete. Speaking as a tech person, it strikes me as hypocritical at best and self sabotaging at worse to maintain this interest in physical space as a marker of success.

But, then the marketing/sales part of my experience chimes in and I think of all the various times in my career that having physical space added to my credibility. I think of the sectors (government tech and financial tech instantly come to mind) where decisions makers are heavily moved by AAA office space. And, I think of how many times I've seen spending an obscene amount on rent actually convert into paying customers.

My inner developer is saying "right on" but my inner marketer/sales type is thinking of all these times when physical space has a positive ROI from a sales/marketing point of view.


This takes extraordinary discipline on the part of the in-office team. Fortunately, everything that's good for a remote-first culture is also just good for communication in general. A culture of documenting everything, living in public, and over-communicating is good for any company; and burning those habits into teammates levels them up for life.


>This takes extraordinary discipline on the part of the in-office team. Fortunately, everything that's good for a remote-first culture is also just good for communication in general.

I think it's even harder for companies that have open open offices or are doing Agile. Those two things usually mean the companies are explicitly stressing in-person collaboration. In-person communication isn't a bad thing by itself, but I think that explicitly valuing in-person communication ends up making remote work harder.


I've worked remote for 6 years. This comment echoes my experience.


This is the best answer.

It is really hard for established companies, full of many different humans with their habits, to shift from shouting across the room to some sort of distributed, async, communication.


I don't understand why companies don't build specific teams that are 100% remote, with perhaps an onsite project manager (or something like that). Then the team could develop its own norms and culture, and while it would be isolated from the rest of the company, it collectively gives the remote workers much more of a voice than if they were each on different teams.


Red Hat v. Debian.

Arguably, one of Ubuntu / Canonical's failings.


Huh? Canonical is excellent for remote work, and I know many people who work at Red Hat who say the same about it.


I meant far more the former.

The Debian - Canonical distinction is milder, though the latter has at least some centralisation. Nowhere near as much RH's.


IMO one of the least-solved problems is communication. Two areas in particular: (1) lack of a shared real whiteboard, and (2) video-call quality.

These are two areas where good solutions may exist at reasonable price-points, but if so that information isn't widely known.

Not sure if it fits with your business model, but it would be extremely helpful for someone to carefully evaluate the effectiveness of various technologies / products / services for those areas, and provide recipes for known-good setups.

I.e., if one of your clients can tell you their current and upcoming team sizes, network connectivities, etc., you can tell them what products and services give them good video / whiteboard quality at various price points.

IME companies with remote workers tend to be "penny wise, pound foolish" regarding these things.

EDIT: To be more specific: For call quality, having good data on what setups result in good call quality in Skype vs. Slack vs. Google Hangouts etc. And for shared whiteboards, having good information on how effective / sufficient teams find various approaches such as (some website + iPads), (some website + a particular Wacom tablet), (everyone on the team having a particular model of interactive whiteboard such as this one [0]), etc.

[0] https://www.cdwg.com/product/SMART-Board-6075-75in-LED-displ...


Anecdotally I can say that Zoom has worked the best for us.

But no software can fix variances in bandwidth or latency. I wish there was a way to test a remote hire's internet connection quality. Lack of access to a good internet connection would be a deal breaker for a remote hire for us.


You know, I might have an idea for you. A few years ago, I built a diagnostics tool for a product whose primary users were using some absolutely horrible internet connections.

One of the most useful parts of it was timing http requests and tracking response times. We solved some very complicated technical support issues using this tool. Do you think it would be useful to adapt something like this to remote workers? It's weird because I've struggled with internet connections when I've worked with remote workers, but never thought of actually testing it until I read this comment...


I believe you about Zoom. Unfortunately that's the only kind of information I'm ever able to get on the topic: anecdotal.

I suspect the reality is that, amongst the best-performing services, which one works best depends on network QoS details, network topology, particular client hardware / OS, etc.

For example: some conferencing software seems to have a real problem with echo cancelation, so either (a) everyone needs mic/speaker hardware that sidesteps the issue, or (b) you accept that everyone will go insane.

Similarly, difference conferencing software has different solutions to people talking over each other accidentally due to latency. One product (Cisco's maybe?) has an icon for metaphorically raising one's hand to request a turn speaking.


We've been trying Zoom lately. Seems pretty good, though we always seem to have issues with everyone logging in to a call. Inevitably we have everyone slacking/texting/skyping out the call ID to just get up and running. After we're up though it all works smoothly


A very important contributor to good call quality is good audio hardware.


Yes relying on the cheap 5-10$ pos mic built into a lap top wont work you need a proper soundcard and better microphones and turn off the auto level/compression on skype.

Doing it more seriously you might even want to use a separate older machine as a skype drone (ie only runs skype) and feed your audio out from your main machines sound card into that.

I had an initial phone call with a firm and it was obvious that they where clustered round a mac laptop - inaudible and very low quality sound.


And also improve the acoustics of the room from which you are calling, put some foam on the walls, etc...


>Two areas in particular: (1) lack of a shared real whiteboard, and (2) video-call quality.

Amen to that. I recently was interviewed remotely, and the voice call quality was unacceptably low- I could barely even understand the questions being asked!


I made a quick colloboration app with video chat and more features including a simple whiteboard. Check it out https://oorja.io


I don't understand the downvotes. I just felt excited sharing an app I built that also has a simple whiteboard. :(


I assume you were downvoted thinking you are "marketing" your app "without context", like SPAM

Don't be discouraged. I checked out your site (and github) Looks nice. I'll use the tool next time I need remote collaboration

Keep up the good work.


5. Managing people

Personally, I find the toughest part to be actually managing the people. You really need to trust your team to be self-motivating which can be tough for a manager to do, especially new ones, because you need to give up some control.

But even though you trust them you need to have a way to measure results. That means being more disciplined and mature in your project planning than you might be if everyone is co-located.

For a startup that is key. Startups often skimp on disciplined project management.

I also find it tougher to do things like say, identify when someone is having a rough time (personal or professional) and take steps to correct or accommodate for that. If a co-located employee starts underperforming but I can see they are clearly checked out (like their head is somewhere else) I might suspect there is something going on at home and adjust my management style with that person. If they are remote it is harder to tell those things. Communication becomes extremely important when body language / behavioral clues are lacking.

So to pile on a lot of the other answers here... communication, communication, communication.


Yes, this is why it's critical to adopt an output/outcome mentality. When you can't see if or when we're working the only signal of status is whether shit is getting done. This should be the only thing you care about, and it should be super obvious of you're project managing correctly.


The biggest challenge with remote is coordination. I've now managed 4 remote teams. The turn-around time between communication cycles with people on the other side of the globe can drastically increase the time it takes to get consensus on issues that locally might take 10 minutes.

I can recall several times where clearly (or so we thought) laid out plans were given over to have them come back a week later with some measure of misunderstanding. The 2 solutions to this have either been micromanaging the remote team, which is painful or time consuming -- or giving the team enough autonomy to work independently, which is risky.


I don't have the studies handy, but the general consensus is that you're gonna have a bad time if your team spans more than nine time zones.

In practice what this means is if you're based in the US, you can either focus on having teams in Europe or Asia, but not both.


I've found a middle ground between micromanaging the team and giving them enough autonomy to work independently. It works best on definable tasks when the remote team's manager is technical enough to do their job on her/his own.

Instead of just a requirements document, give them a requirements document but also define a set of red/green tests to show whether the requirements were met. It's hard to do this with front end, where feel is often very important, but in my experience, it works well provided that the remote team's manager is qualified to make the types of architectural decisions necessary to pull this off.

You can even start tying compensation into passing red/green tests!


That's not likely to be a good idea re the compensation. There are a lot of studies showing knowledge workers perform more poorly at the task with financial incentives.


This is either an unfortunate reality or a limitation of my experience, but I've only had to resort to writing red/green tests when my remote teammates have been at a level where poor performance would be something of an improvement. It's more useful for me when I see tons of commits, yet no forward progress on a measurable goal.


Young founders with zero or near-zero management experience in person, never mind remote. To a lesser degree - and strictly for small team, early stage startups - part of the journey is living it together. The whole vibe loses something when you're staying late and eating ramen together over Skype.


It’s been my experience that many first-time entrepreneurs and in many cases first-time managers / executives, operate from a place of fear. They are scared about their burn rate, about whether the team is working, whether they have the right team, about countless administrative details, and on top of that the good ones are hopefully out there actually talking to prospects and seeking customer feedback. What this means is that many are scared of remote because they feel like they need you there present next to them in order to feel like there is forward momentum in the business. It’s a trust problem and a management problem; maybe not even a legitimate problem so much as an emotional burden. Is there a technical solution to that? Some might say the solution revolves around time trackers and project management tools, but I’ve seen those just become a further burden to the team without actually relieving anyone’s general overbearing need to micromanage the team (something they can control) over engaging with prospects / trying to grow the business (something harder to control).


I'm the founder of a company that is ~250 people, remote first, and still fully remote. We do have an office in SF, but ~10% of our employees are present, almost no full teams are centralized, and all our processes revolve around remote work. Important to note that we're a US-founded company (this comes along later).

I'm going to use this comment as a way to talk about remote hiring generally, rather than respond directly to your comments. I want to help others understand some of the challenges it has been being one of the larger (relatively) fully distributed companies.

I think there is a common misconception that the world is mostly flat and that our company can hire from anywhere. I am commonly criticized when tweeting job postings (almost always remote) when the countries we can hire from is limited to a select few. "Not real remote" "first world remote only" "remote != 8 countries" etc. are common criticisms.

Disclaimer for the remainder: I am not a lawyer and my exact details because of that may be wrong. Please consult your own legal team.

When hiring remote, there are a few things to keep in mind:

1.) You have to adhere to employment laws within the country you're hiring from. Employment laws vary widely between countries and getting them wrong can be very expensive. For example: vacation time will vary, holidays will vary, the ability to let someone go will vary, what you can/cannot expect from an employee varies. In one country, emailing an employee outside of work hours is legally considered harassment; when working with multiple timezones that's a challenge because "in work hours" for one country may be "out of work hours" for another country.

2.) To employ someone full time, many countries require you to have a legally entity within that country. Establishing a legal entity takes a lot of time and a lot of money.

In the past 12 months, we've had at least one member (more now) on our HR/finance teams establishing legal entities _full time_. I've had my signature on at least 8 incorporation documents in the past 6 months. By the way, most incorporation documents require a "wet" signature so if you're remote like we are, be prepared to be FedExing a lot of sensitive legal documents around.

Beyond just paperwork, there are often requirements to establish a legal entity: a real, physical, local address is one. In one country, we had to pay out of a local bank account in local currency (which has its own red tape), and this country also required we maintain a minimum balance to pay 3 months salary in the local account in local currency at all times. For a startup, that much cash "not working" can be problematic depending what stage you're at.

In one country we're establishing an entity in, the process just takes a LONG time. We've been responding to any inquiries and sending paperwork immediately and we're 8 months in and still probably 2 months away from completing the process. Meanwhile, we still can't legally hire there.

A lot of legal paperwork is understandable in the local language of where you're creating the entity. This means that you also have to pay lawyers fluent in that language to vet the paperwork. We employ full time lawyers, but primarily in English, so this requires us to go to expensive outside counsel.

Finally, this is all expensive. There are fees to creating entities but also recall that we have multiple full time employees that spend their entire day establishing legal entities. So we have our own full time salary costs plus filing costs plus legal costs.

3.) Hiring contractors DOES work around some issues, but has its own downsides. First, we can't offer options/stock to contractors and we'd like all our employees to benefit from this. Second, we often can extend the same full time benefits we want all our employees to share such as healthcare, 401K, etc. Put another way: we want all HashiCorp employees to be employees, we don't want to create second class citizens.

Legally, some countries have legal limits on the hours a contractor can work or length of time they can be contracted before they're considered an "employee" by default and regardless of what you SAY the relationship is, the country will consider it employment and points 1 and 2 above all take effect immediately.

So we certainly DO hire contractors but our point of view is that we intend to hire those people full time over time. We'll often hire contractors if we know that we'll have a legal entity established to hire them within X months, and we're up front with the new hire about this. We'll also pro-rate option/stock vesting for their contractor period when they are hired.

4.) We prioritize countries where we have the most interest. We get asked a lot "please hire in X" but if the number of times we've heard X is much lower than Y, then we'll prioritize Y first.

This creates somewhat of an imbalance, since more countries with a more established tech ecosystem generally have more qualified candidates and therefore get prioritized higher.

We WANT to hire from everywhere, but as a startup with constrained capital and timelines, we have to be pragmatic about choosing the locations where we'll probably be able to hire the most roles while we continue to expand our entities.

5.) We are also open to relocating employees into countries where we do have entities. We've done this multiple times, we pay a relocation fee, and its a great way to hire someone from a country where we can't [yet]. Also note they're "relocating" but are still working remote.

Of course, this is highly dependent on the individual and it is unfair of us to ask or force someone to do this if they have an established family, friend circle, and generally just a life in their existing country. So this only works some of the time!

6.) Despite building process around remote-first, we try to a keep a healthy timezone overlap in each of our teams (3 to 4 hours out of the working day is best). We find that teams that have a team member with a non-overlapping TZ struggle for multiple reasons. So, even though we can hire in many countries now, we'll restrict some job postings to certain countries so we can have that overlap.

EDIT, some additions:

7.) Each US state ALSO requires a legal entity in addition to adhering to state-local employment laws, taxes, and more. At this point HashiCorp has entities in ~30 US states.

Further, there is a tax consequence to the business outside of employment taxes. If you hire an employee in a state, you also now have to pay sales tax on revenue from there. You may argue for/against whether that makes sense, but for a startup this can be VERY expensive.

Our corporate tax obligation would be hundreds of thousands of dollars [less] if we didn't employ people in New York state. We've had to weigh this in cases because the tax obligation from hiring _one_ individual could suddenly be that you can't afford to hire _multiple_ other individuals.

Note we don't want to avoid taxes, that's not what we're doing. But startups are capital constrained and we have to determine long term how we continue to grow and hundreds of thousands of dollars can make a difference.

----------------------------------------------------

Finally, I want to note that we're 100% dedicated at HashiCorp to remaining fully remote. We WANT to hire from everywhere. We're establishing the entities and process to hire in new countries full time. 18 months ago we could only legally hire in 2 countries, today we can hire in 8. By the end of the year it should be at least 4 more. We'll continue from there.

I could write a LOT more about culture and process within the company. But this comment is already getting very long and I think I'll keep it to this. Maybe in the future I'll write more about "chat literacy", the importance of decision inclusion, things that definitely don't work, keeping people motivated/happy, managing people you can't physically see, the lack of body language for signaling, and a lot more.

I hope this helps someone!


My company hires engineers wherever they are. We're only incorporated in a few countries, the way we work is to engage a firm whose business it is to be incorporated in many countries so that they can hire people in those countries as full time employees, and contract them to our company. This firm charges a flat fee per person per year, and it's not a lot. I've been told that we'd have to have at least 5 people in a single country before incorporating in that country would cost the same as using this firm. They handle all the local obligations, payroll, entitlements, tax, superannuation, etc. I don't know how it works, but we even are able to get stock options, and I've never heard of any problems with that from any of my coworkers in any other countries. Other things like leave - our local job contracts conform to local law for leave allowances, and then we just work it out with our managers - we have an HR system that seems to be able to easily handle different leave policies for each employee, and if there's any problems, you just tell your manager and it gets sorted, no big deal.


Mind sharing the name of the firm?


Not the OP but we use a firm called Velocity Global for exactly this. Though they take a % of salary, so would be interested to hear who the OP uses too


Thanks for the all the details here — really useful!

We're a remote team but much smaller and certainly unable to pay a full time employee to create companies.

Do you have, or know where to find, a list of countries that can work without setting up a legal entity? We've lost a lot of time trying to recruit candidates where we've not been to find a workable solution due to local laws and our limited resources (e.g. in France!)


I don't have such a list, sorry.

Learning about this stuff basically requires a huge time sink per country in reading local laws, as well as a cost of paying a lawyer to verify your assumptions. It is unfortunate. A "tldrlegal" site for entity creation and employment laws would be amazing.

Also re: France... yeah, that is a tough one. We're just about ready to hire there. The whole process was very difficult, on the harder end of the spectrum that we've experienced so far. :)


> First, we can't offer options/stock to contractors

Can you elaborate on what is keeping you from offering options to contractors? Sure, incentive stock options can only be given to employees but what about nonqualified stock options? They can be given to anyone.


Tax and legal issues for example in the UK (one of the more friendly countries to the idea of employee stock ownership) there are rules about how an approved share option schemes work- main one is no multiple share classes.

Whilst you can offer on approved schemes - you might have to offer people in the uk more options to cover this which might make local (US employees) jealous


> Note we don't want to avoid taxes, that's not what we're doing.

Tax avoidance is perfectly legal and encouraged to maximize shareholder value. Tax evasion is illegal.

> First, we can't offer options/stock to contractors

Can you elaborate why?


What a fantastic post. Thank you Mitchell.

Would you be able to share the actual countries in question? In which country was it required to open a bank account in the local currency? Which one has taken 10 months to complete opening an entity in?


Thank you very much! For the HR perspective, here a post about remote / international hiring some time ago. More a culture and learning approach. https://blog.giantswarm.io/10-insights-of-international-recr...


My (former) company's experience report: https://medium.com/@davidrupp/we-actually-built-a-remote-tea.... Less about HR/Legal, more about culture and approach.


asking for a friend... what if you hire someone 'Alex', a resident of Washington State and then they move to Germany because their spouse is relocated for employment to Germany, where they both receive benefits but are required to remain US Citizens (and return to the US each year)... in that case are you paying Alex as if they are a Washington State resident or are you legally required to pay them as if they are a German resident?


Disclaimer: Not a lawyer, consult a real lawyer.

I don't know for the specific case you've posed, but we've had similar things happen. If an employee moves into a state/country we can't employ them in, it causes a bit of a panic. We either have to 1.) establish the correct legal/financial entities to employ them or 2.) let them go. In theory, you can convert the employee into a contractor, but this has ramifications on options vesting and benefits and so on and is a huge mess. I'm sure there are a lot more caveats to this that are under consideration (again, I'm now a lawyer) that may affect this, so I wouldn't generalize this too far.

I don't think we've ever let someone go for this though, we have once to memory panicked and rushed to establish the entity (potentially paying fines along the way). I may be mistaken, I just don't recall exactly. In any case, we kindly ask our employees to notify us of any change of location, since it almost certainly changes payroll tax even if you are moving to a location we CAN employ in (i.e. even between US states). Also, the panicking is not fun for anyone (including the employee, whose job status is suddenly uncertain).


As soon as you start working on German soil, German employment laws apply fully. Citizenship, prior residence, etc. are almost completely irrelevant. There is a social security agreement between the US and Germany which might exempt the person from German pension contributions but nothing more.

(If the spouse is working for the US military there are NATO agreements which might make German employment law inapplicable but I know almost nothing about that.)


Make sure and include a "Gerichtsstand" in the employment contract. This is basically the name of the city in Germany where legal processes related to the contract will be conducted. This will save you a good deal of unpleasantness later, should any employment issue come before a court of law in Germany.


This is really interesting, thanks. Would love to read your thoughts on chat literacy and the importance of decision inclusion.


Super insightful, thanks for sharing. Wondering if it's easier to be a remote-first company from other countries.


very interesting post, would mind sharing your top 10 countries to hire remotely


Thank you for taking time to explain. Very helpful and very interesting. Cheers!


Glad to see employers are breaking hiring norms


Great post! Thanks. Contractors FTW :)


Great post, many thanks for writing it.


Infrastructure & working space is a big challenge depending on where your remote team member is based, but overall that has seen a big improvement with more affordable UPS options and wireless connectivity for backup.

Timezone is a tough one. For us, finding a scrum time that works for everyone (in a small team it's doable), and sticking to it daily helped to get the team to communicate more openly with each other, and stay in sync.

Finding the right set of tools to manage remote teams is one the biggest challenge when a team is distributed across the world. Traditional task management tools didn't lets us easily ideate, organize, and share task lists together, hence we were inspired to build Taskade (Disclaimer: I'm the co-founder of https://taskade.com). The idea of having the freedom to work together on task lists in real-time, see each other's progress, and collaborate without any distractions.


Communication.

Communication! Communication! Communication!

If any part of your product requires people to communicate with each other, then the team members lying on vastly different time zones will have low efficiency because information round trip time will be larger than those of the local (or time zone near) ones.


Yes, Specifically being able to communicate in front of a whiteboard is crucial. Exploring ideas, creating a shared understanding, etc, all becomes a lot easier if you can support this with some interactive visualization on a whiteboard. I feel disabled if I have to communicate without a whiteboard.


Personally I'd say 1 and 4 are the most pressing, though 2 raises some other issues. Personally I'd not hire anyone junior for remote work at all (sorry), so 3 is an anti-issue to me.

Hiring is hard to begin with, and hiring remotely has additional pitfalls. A company like Triplebyte that would perform additional vetting to prove a candidate's ability to work remotely would be quite welcome.

Re 4. VC systems are still awful and both companies and employees aren't willing to invest to the right level, and commit to workflow changes, in order to make it seamless to work remotely. In particular, latency and packet loss is what just kills VC and makes it very apparent that we're not actually in the same room together. The way to solve that is gigabit home-office Internet connections, but $10k to run lines and an additional $500/month, as well as the hassle of using a wired connection at home to take advantage of it, and then a dedicated VC system, is a total non-starter for many, on both sides, employer, and employee.

Throw in a timezone difference, and the wrong remote employees can take more time to manage than they're worth. (That's not to say there aren't some really really good, really solid remote employees, just that there are also the wrong hires - same as goes for in-person.)

Re. 2. On top of payroll, there are also plain cultural differences between countries that make it more challenging than when there is no difference - holiday schedules, vacation policies, etc, and until you've lived it, it's hard to know what to look for in advance.


We are a pure remote company but Tax/employment-law is for us the biggest issue. Or to be more precise, it's the biggest issue for potential co-workers. We find that people are super interested in us, but when we tell them they have to do their own tax and basically act as freelancers, most say no to us. The majority simply wants a standard legal employment. Which I understand and I would like to have that too.


I keep seeing in remote job posts for US companies that you need a work permit, they don't mention the option to work as a freelancer. In the Netherlands a lot of people work from their own one person company.


I doubt that "do their own tax" is the blocker there, I would expect it's much more about "give up on any kind of legal protection as a worker."


As a Canadian who has worked remotely for US companies it is pretty standard to be paided this way and makes employment a little simplier.


Google PEO and stop handling it yourselves.


As a few others have said as well, the biggest challenge personally has been Payroll and Taxes. A lot of good candidates want to feel part of the company which means they need to be hired as employees. But legally, a US company hiring in a different country can at best hire them as a consultant/freelancer for tax purposes unless they open a local office in that country which is a major PITA.

I have a US company and trying to build a remote team as "employees". Going crazy trying to figure out how to set this up other than the usual option of "pay them as freelancers and let them do their own taxes". Not everyone is cut out for that and not able to attract good talent.


We[1] are a fully distributed team and also ran into this problem when we hired our first team member outside the US. There are lots of players[2][3] in the "Global PEO" market that have corporate entities in multiple countries and will handle payroll and benefits for you, but caveat emptor, these solutions are shockingly expensive. The average cost was 18% of the remote worker's salary (!), which I personally considered insane.

We ultimately went with a company[4] that had a different model where they connect you with a local PEO in each market and present a common UI on top of all the disparate local PEOs so that you get a company that specializes in just that country, but a common UX no matter how many countries you work with.

I liked the model, and more importantly, it was a fixed fee and much less expensive, and they published pricing. Disclosure: We made the decision to go with them, but haven't started working with them yet.

[1] https://gruntwork.io

[2] https://www.globalization-partners.com

[3] http://globalpeoservices.com

[4] https://papayaglobal.com


From the comments so far, I'm hearing that your prospective clients would benefit from knowledgable consulting to help them navigate multiple issues:

- Which payroll companies, if any, will be the best solution for handling international (or even just inter-state within the U.S.) payroll / tax issues?

- What communications technologies and practices work best for various team geographies / network-connection-quality / local-hardware setups?

- What's the optimal frequency, duration, structure, etc. of whole-team face-to-face meetings for teams that are typically distributed?

- What management training is most helpful for managers of all-remote teams, or of teams where only some members are remote?


Another comment about consulting services: Client executives might really benefit from a clear (and accurate) presentation of the different levels of remote-team-collaboration quality that are available at different per-employee price points.

For example: At ($10k initially + $3k/year) per employee, you're likely to avoid problems A, B, and C, but still run into D and E occasionally, depending on team size, using recipe $FOO.

At ($20k initially + $10k/year) per employee, you avoid problems A-D, using recipe $BAR.


Payroll is the biggest issue. You have to pay taxes in any state your employee is working. This gets expensive and time intensive as you start filing annual reports and paying taxes in 4 or 5 states.


When I ran a business, having a tax preparer really helped with this.


I'm confused by people saying they have problems communicating across the internet due to conference software. Gamers have been running 40-people fully-coordinated real time raids and a company can't manage to run a meeting online?

How people have problems every day with the conference software? If you do, buy a dumb hardware that you use only for conferences (I think a raspberry could work too?). Or join 2 minutes earlier than your meeting and run a sanity check.

Connection will drop once every 10 meetings, but so people will get distracted, or sick.


Startups often don't know how to hire let alone hire and manage remote, and quite often, remote workers aren't always the best at it too.

What could work quite well often is more challenging... Some things that have made it easier for me:

- Dedicated PeopleOps person - this person's job is only to make all the tools work together better for everyone. Jira, Slack, integrations, notifications. People should be able to open requests to remove remote friction of using multiple tools, etc.

- Start with real-time remote (everyone who works is awake at the same time) has gone a long way. Plus or minus 2-3 time zones, no more. That way, especially in the beginning, everyone is available to work at the same time.

- International payments, in the beginning, is easier to start as a contractor via a service that takes care of it like Upwork. Once you know you have a winning candidate, it's worth figuring out that new jurisdiction.

- Onboarding - should be collaborative, hanging out on slack. Make candidates join your infrastructure during the trial period to confirm that in fact, they can use your tools.

- Read - there are lots of companies building healthy online cultures. STudy and follow them.

- Weekly WOS video call - 1/2 hour every week for everyone to have 1-2 to minutes to share what they're working on.

- Run all meetings as if they were remote. Everything gets scheduled on hangout, etc, in case someone needs to hop on.

There's some good handbooks out there for remote working too that have been a treasure trove. If I can find a link I'll update this post.


I have been working at GitHub for almost a year, which is a remote first company. I would say challenges include:

- Solitude (at first it's not an issue) - Asynchronous communication. Learning to read and write effectively. - Team collaboration work (designing/brainstorming). It's very difficult to explain ideas through <insert name of video conference product>. To solve for this, GitHub allows employees to meet each other as long as there is a business need. On top of this, we hold summits very often, where the team gets to meet each other in a location for a week. - Internet and great conferencing hardware (GitHub provides a great budget for both Internet costs and hardware).

But I would say the most challenging part is Trust. Trust in your manager, trust in your organization, trust in your company, and trust in your peers. Without Trust, there is no way to build a remote friendly company. How are you going to micro manage someone who is working in EU while you are sleeping in the US? Obviously GitHub is not a perfect place, but I would say that there is a mutual understanding among employees to trust each other and to communicate effectively.


> To solve for this, GitHub allows employees to meet each other as long as there is a business need.

What do you mean by "allow". Is it, in general, not allowed for employees to meet each other in remote-first companies, but GitHub notably allows it? Or did you say it that way to emphasize they must meet only for business needs and not for anything else. If so, why? Would you be able elaborate on that sentence?


As in GitHub will cover all the costs (flight + hotel + other expenses)


They probably mean that GitHub arranges meetings and pays for expenses.


Can I ask a question? I personally have never been in a relationship with remote workers that has been more than 70-80% as effective as having everyone co-located.

What are some examples of companies that have been successful using primarily remote workers? I don't mean companies that Hacker News considers do remote work "correctly". I mean companies who have grown to around the nine figure mark without a co-located team?


WordPress. Matt Mullenweg has given frequent interviews about how their "remote-first" culture works. Here's a starting point of articles and interviews he's given: https://www.google.com/search?q=matt+mullenweg+wordpress+rem...


GitHub has ~800 employees, almost 70% is remote


Zapier maybe?


None of the above. Few engineers (or other individual contributors) have the operational maturity to work effectively remotely. Few managers have the skills to manage remote employees. Few employees have the insight and communication skills needs to work as effectively with remote colleagues as with those who are present. These issues magnify the larger and organization gets.


Payroll 100%. When we started hiring people remote it was the biggest surprise, and most headache.

Trying to figure it out on your own is irresponsible at best, so it boils down to hiring a local CPA or tax attorney in each state/city you hire in to go over the implications of bringing someone on in that city.

If the person is right, it's worth the cost, but it's a large, unexpected time-suck.


This problem is already fairly well solved by professional employer organizations like Justworks, Paychex, Extensis HR, etc.


And if you're hiring someone in another country?


I don’t know what the best answer is. We currently treat international employees as contractors.


Remote tech is unreliable. Our company spends tons of money on conference software, and we still all sat around for 20 minutes of a wasted meeting today while they couldn't get a weird echo out of the dial-in. There's always something- we can hear you but we can't see you. We can see you but we can't hear you. The slides are showing but the video isn't working. The video is working but the sound has a weird echo. Everything is working, but someone forgot to put themselves on mute and you can hear the driving noise.

Even when everything works perfectly, there is always a lag or a missed connection due to miscommunication or timezones.

In short, it always kinda sucks, is a drag to deal with even with the best tech and we just get more done with our in-house teams.

Remote workers don't build up any social capital and so are always the first to be laid off.


After working remotely for over a decade for multiple companies my conclusion is the biggest issue is finding managers who grok remote working.

If the person in charge doesn't know what he's doing the rest doesn't matter.

Regarding your options:

1. Hardly any different than on site. 2. Not an issue at all. 3. Huh? 4. For some.


Do you have any suggestion on how to spot a "bad manager" in that regard?

My recent experience left me a bit scarred.


0. bandwidth

There’s no solution as good as yelling across the room or walking past the desk. chat is a poor substitute for all the reasons everyone in this boat knows.

The best way to get this to work is like that one company did (saw it here on HN): have everyone in the company work remote for a week.


We hire remote.

None of these are big problems. The biggest problem we have is communicating effectively with people in various time zones, and making them feel apart of the team. Video conferencing is still an area that is lacking in this area. I've yet to find a service that meets all our needs. Right now we are using LifeSize because it's the best we've found, and still fairly annoying.

The problem really isn't on the "hiring" end. It's how to work as effectively with remote people as you would with people in the same office. When you introduce friction with remote, it causes problems. That being said, I think it's a worthwhile problem to solve.

Not sure this helps, but this is our biggest struggle right now.


i do not work for zoom, but lately our company switched to zoom after using webex, skype, skype for business, polycom, cisco. hands down zoom has been the best solution for video conferencing, works really well.


totally agree with you on zoom -- also, zoom's slack plugin makes starting meetings quite easy.


I can't remember if I read it here or somewhere else, but someone once made a really good point: that the incentives are strongly skewed against hiring remotely.

Think about it: the benefits of remote work go mainly to the employee, but the drawbacks (harder to communicate, harder to evaluate productivity) fall disproportionately on the manager. Since the manager is the one making the hiring decision, they don't hire remotes.

So to give a really broad answer, my suggestion would be "change the incentives so managers will hire more remote workers". That could mean internalizing costs of on-site workers, better communication tools, etc.


Pay late stage startup employees & new-hires to keep a time diary, and see where they spend time with coworkers. Then do the same w/ people not working at startups. I guess that startups have more "non-work" time spend together.

Joining a startup is different than a 9-5 commitment, it means joining a tribe/family. So if the office people leave for a 2-hour lunch before spending a late night in the office, how does a remote person "join" that? Being part of the family means you are there for the leisure as well as the work.


I work frequently with startups / early-stage companies and have not found remote to be a legitimate problem or any different than the experiences encountered by established companies with regard to working remotely. Managing international payroll, or frankly even dealing with tax and regulatory differences among the 50 states is likely something many startups would be willing to outsource. Just dealing with several states was a burden, plus the administrative costs of a payroll service felt like a lot for the service received.


Security is the big problem, even if not international. You essentially have to connect computers with trade secrets (source code, CAD files, etc.) to the internet, which is a big no-no.

If you go international, then you are probably dealing with a legal system that is stacked against you. The government probably even intends to divert your trade secrets to fully domestic (relative to them) companies, and will apply pressure to "your" employees (who may even be government agents) to make it so.


#4 is the most pressing. I have a fully remote team, and we try to make sure as much communication is asynchronous as possible. But sometimes, you just need a few people to work together in real time.

And right now that means dealing with a terrible video conferencing experience and not having a good shared whiteboard solution.

If you could figure out a way to realistically replicate "a bunch of people around a whiteboard", then I will pay you money for your product.


We have been working remotely from day one. It was difficult at the beginning and can feel harder sometimes, but once you get used to it it works. The team meets also every few months in beautiful places like Italy or Spain and spends a few days together. This is how we get over problems like "isolation".

Our set up has partly brought us to create ellyot.com that allows you to find inspiring workspaces globally and network with like minded people.


Everybody speaks here about communication. With the rise of enterprise messengers like Slack it's becoming easier.

For example, bots like http://tatsu.io or http://standuply.com help running standup meetings.

I think remote work will become more and more popular in the future despite its challenges.


I'd say #4. I am remote and my company has a hard time providing, tracking, maintaining, and upgrading the gear employees need to do their job. It currently involves a lot of manual data entry, trips to the UPS store by both HQ staff and remote employees. Especially an issue when the person who is ordering gear doesn't understand the gear or the needs of the employee.


The gear is not computers, right?


They must be big, because it seems like every startup has to put their HQ in the most miserable places like Mountain View or Menlo Park.


We're a new b2b saas company. We just made this exact decision (to locate in sfbay) and the decision not to hire remotely. Reasons to be here are basically we have a deep engineering network for hires, we raised $300k from local angels, most VCs we want to work with are local, and most of our desired customers have their hqs here.

Reasons not to be here are the absolutely ludicrous cost of housing and what that does to salary requirements.

But as a tiny company, execution speed is our single most important attribute and we couldn't work out how to work remotely without damaging that. I'm glad github and others have managed, but you have to wonder if they succeeded despite being remote.

ps -- I've worked remotely before. It's really nice not to start every goddamn meeting screwing with hangouts doesn't connect / lifesize hardware works great but doesn't connect well to mixed hardware + laptop calls / multiple zoom invites with different meeting rooms / go2meeting clients are shitty / etc.


Biggest challenge has to be timezones. Just due to the delays in communication, and the difficulty of having meetings late at night or super early in the morning.

I've found the most difficult type of remote work is highly collaborative. Iterating on designs, on software, or ideas in general.

Anything that can aid in that type of remote work would be a boon


I think the hardest part is the planning process and communicating rapid change.

Startups and fast growing companies grow quickly and changes happen rapidly. If priorities are constantly changing and communication/the planning process isn't really robust you won't have remote people who are successful.


  - International payroll: often impacts tax situation
  - Adjusting to remote collaboration. e.g. no more walls of sticky notes; can no longer rely on water cooler conversations or "quick meetings"
  - Timezones


These are more important barriers from my experience. The other areas mentioned already have some type of incumbent solution in place.

Problems 1-4 only become real problems after the management team feels comfortable with:

5) How are we going to integrate them into our workflow and team?

"Hire remote workers" has become an extended and rebranded form of "offshoring". Folks learned some hard lessons from the offshoring days that you can't just hire remote. Your organizational thinking and processes need to be ready.

My take is, if you're solving 1-4, you're selling to companies who already have some remote workers. If you're focused on companies with few to 0 remote folks, you'll need something to help them solve 5.


What exactly is the pain with international payrolls? I don’t quite understand..


Country A requires all employees to receive a default-opt-in pension.

Country B requires employers to register with tax authorities and deduct tax directly from the employee's salary.

Country C allows employees to buy childcare vouchers with their pre-tax salary.

Country D has a similar scheme, except for bicycles and it's a loan.

Country E considers private healthcare a taxable benefit-in-kind.

Country F has three different tax bands for employee stock options, depending on when they can be exercised.

Country G makes it mandatory to provide flexible working for new parents...

Of course in a lot of cases you can save on admin by being less tax-efficient, like by not participating in tax-efficient government incentive schemes.


It's only a problem if you actually want to hire them as employees. Otherwise paying workers should be as easy as just wiring money to their bank accounts. It's worker's problem to figure out the laws in their country: do they need to incorporate, how to pay taxes etc.


Dealing with taxes and with contracts in different jurisdictions. Sure, some people may be ok with working self-employed and handle all of that themselves, but not everyone will do.


Somebody should build startup which would solve payroll issues with remote employees.


Is it profitable / worth the effort?

The US has 300 some million people. India has a billion some.

If you can't find an employee in those two countries, it seems you have other problems? (or add 1 or 2 more if you want to spread it around).

Not that there are not great people in all countries. But opening your resume pool from say 1.5 billion people to 3 billion people is unlikely to have a huge benefit to hiring.


So tell me, how do you employ someone who is in Germany if you are based in the US? Germany wants its taxes so you can't just put them as a regular US employee and you don't have any presence in Germany so you can't hire them locally.


Even hiring within the US remote workers can cause issues with the "tax nexus" as a remote worker acts as a physical presence in that state, forcing the company to pay taxes as if they did business in that state.


just sending someone money can be a problem. not such much in europe but try getting americans to send a wiretransfer...


Trust building/erosion and buyin/retention.


Co-located work is synchronous programming.

Remote work is asynchronous programming.

The great part of co-located work is that so much communication happens organically. If you need something, or have a question, the answer is a desk or two away. Processes can be ad-hoc and decided in the hallway or around the water cooler.

At the same time, that organic nature turns on a company once it gets bigger. The organic transfer of information takes time. In small organizations or teams that time is small, but as the organization or team grows, the more repetition is needed to propagate the same information in the system. Where you used to answer a question once, it's now once a week.

The reason is because the ease of organic communication prevented the organization from writing down it's tribal information. It took too much effort! But as the organization grew, that slow organic information transfer simply could not propagate tribal knowledge fast enough or redundant enough like writing it down. Remote work is essentially permanent async work, but you are also temporarily async at 3am and your servers are down. I hope your coworkers wrote the production debug steps down, or you are relying on your own memory. It also affects your new hires because they will have to enculture themselves to the information and organization.

Remote-first policies see that, eventually, all companies require async access to it's tribal knowledge. That's READMEs, Wikis, tickets, helper programs, the accounting department, etc. Realizing that all corporations are eventually remote (if only because you will spread to another city, office, or different floors), you spend the extra energy to build those tools so you can look up your tribal information at 3am on a Saturday morning after drinking. Those Wikis really help, yo!

It also adds a tremendous amount of visibility and accountability into what you do. You have visible documentation and visible communication. Tickets are filed for bugs, and others in a completely different office can check the status. My drunk self can read the production FAQ at 4am before the hangover sets in. The best part is you can hire remote workers, because your entire process supports that asynchronous access to information.

In many ways these asynchronous processes add a tremendous amount of value to your business, as well as offer the perk of hiring fully remote employees.

Why, given all of these benefits, would companies bother with co-location at all? Well, to borrow from Behavioral Economics, I'd say they are making an economically irrational choice to value the show of productivity over actual productivity. Management by visibility. I do think management types are incentivized to continue the show, rather than the substance, because their boss judges based on visibility rather than metrics. At the same time, the fixes are spelled out above since they add that visibility into processes (to an extent), but it takes a management that holds itself accountable.

For another stupid geeky metaphor, businesses are highly parallelized processes. A synchronous co-located organization has highly mutable information sources, it's employees. To get information in such a system, that it must acquire a mutex lock (interrupt the employee) to read information but it's faster for both people. A asynchronous organization, through it's explicit processes and documentation, allows for lock-free reads of information but requires more overhead on the individual processes as well as embracing some Eventual Consistency. In a small organization with few employees/threads and few interruptions/locks, co-location probably is fine. But as your employee/thread count increases, those locks and interruptions exponentially explode and your whole organization can grind to a halt in endless Slack questions and status updates: The Deadlock of Corporations.

If you are thinking about remote, consider tools that embrace asynchronous access. IMHO this means any software that requires both parties to participate at the same time is bad. I'm including Phone Calls, Slack, IRC, AIM, Email, Hangouts, and others like them. You should never have to ask "Did you see/read/notice my X?" as these tools encourage synchronous behaviors. These processes are the Interfaces of your Organization. They increase overhead but they pay dividends when your organization grows in headcount. The ability to hire remote is a perk at this point.


How does 2 normally work? Apart from invoicing as a contractor, can the company actually hire someone located in another country?


Skill qualification and the more formal communication requirements.


For us (http://fairpixels.pro) it’s actually the off-work connectivity. Slack, email, todo lists and all of the other tools make us pretty effecient and productive. But I’d love to see how I can boost social connectivity outside of ‘work’.

PS. We are hiring


Do you have a hiring page on the fairpixels site? I couldn't find one




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