Remote & Async Work 8 min

The future of remote work: Insights from Gillian O'Brien

Written by Gillian O'Brien
May 17, 2024
Gillian O'Brien


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With 28% of employees working remotely worldwide, remote work is an expected lifestyle for top companies and talent.

Organizations and individuals who prepare for the future of remote work know that return-to-office mandates are not effective, and look for answers on how to navigate the new wave of remote work. To do exactally that, Yarden Berkman, product marketing manager at Remote, is hosting this discussion on the future of remote work. In this interview, Gillian O'Brien, general manager of Remote Talent, shares her thoughts on how businesses can thrive in the next chapter of remote work.

Changes in remote work

Yarden: How is remote work changing currently?

Gillian: Remote roles are unbelievably popular — especially as more companies enforce return-to-office policies as a way of “quiet firing.”

While only 20 to 30% of open roles are remote, they attract over half of all applications. Remote jobs are the most desirable roles by far among job seekers, making the market highly competitive and challenging for both applicants and employers trying to identify the right hire among an enormous pile.

Future of remote work

Artificial intelligence and machine learning

Yarden: Looking ahead, what emerging trends do you see influencing how companies attract and recruit remote talent?

Gillian: AI is a huge emerging trend in hiring — although it’s been around for years. Machine learning is becoming powerful enough to work very well for matching resumes and job descriptions. Remote Talent aims to bring the same sophisticated search to job seekers who want to identify best-fit roles.

More importance on collaboration

Yarden: How is remote work in the future different from remote work now? 

Gillian: As remote work becomes more the norm, one of the hardest things will be collaborating with and managing team members across multiple time zones and locations. Remote work in the future will be better at this — managers will learn how to engage their cultures and keep momentum going.

Challenges and opportunities in the future of remote work

Yarden: What are the challenges and opportunities that remote teams will face over the next decade?

Gillian: Regarding opportunities, any candidate will be able to work at a global company, and companies will be able to hire the best candidate regardless of location.

One of the biggest challenges in the future of work will be maintaining community. There’s already a lot of conversation around the disappearing “third place.” With remote work becoming the desirable norm, many people even lack a “second place” because where they work and live is one and the same.

Strengthening a bond with your colleagues does not happen through sync calls (or even in-person) happy hours, though. It comes from legitimately working together toward a shared goal. So remote-first and 100% remote companies will really need to have strong, charismatic leaders and deeply mission-driven cultures to help employees connect to something bigger than themselves.

Tips for employers preparing for the future of remote work

Maintain consistent remote work policies

Yarden: What remote work mistakes will cause businesses to fail? 

Gillian:‌ Not committing to a policy, one way or another. A lot of companies are trying to figure out what works for them — in-person, hybrid, remote… but in testing the waters and experimenting, the consequence becomes these weird non-commitments to any real policy.

For example, some companies are mandating in-office for all employees hired after X date. How can half the company be remote and the other half be in person? The experience seems terrible for employees. Even a hybrid mandate for employees within X miles of the office is pretty demoralizing when only a handful of people are ever showing up. RTO exceptions for some employees and enforcements for others is also not a good strategy and doesn’t send the right message to anyone.

Focus on outcomes

Yarden: What consequences (good or bad) will remote work have outside the workplace that you don’t think people talk about enough? 

Gillian: Some people will be working a lot more, others a lot less. A 9-to-5 work schedule used to sort of standardize this. But with remote work, some employees will not disconnect and will be working way more than they should. Others will be under-working. Being outcomes-focused vs. monitoring the number of hours spent on a task is probably a better way of evaluating a team.

Connect your tools

Yarden: How do companies easily hire remote employees?

Gillian: Consolidate your tools. As much as possible, employers should aim to use a single platform for finding, hiring, and paying talent. The less your team and your applicants need to familiarize themselves with multiple tools and platforms, the faster things can move.

Find the right remote work candidates

Yarden: How do companies find the right remote candidates?

Gillian: Choosing where and how to advertise your role is key. Stick to platforms focused on remote work specifically. General job boards fail to let employers be specific about time zones, locations and relocations, and visa requirements. They don’t provide the appropriate search filters for candidates, either. So you end up with a flood of applications from people who just aren't the right fit.

Employers also do not need to pay to further promote their listings. Remote jobs are already pulling in more applicants than peer ads. When a job platform is asking you to sponsor your listing with a daily budget, this is usually a revenue-generating strategy for the platform, not necessarily aligning with the actual needs of the employers.

Tips for employees preparing for the future of remote work

AI isn’t everything, so hone your strengths

Yarden: What is the most significant way a job seeker can prepare for future remote work?

Gillian: Everyone says AI, but I don’t think people should waste time trying to strengthen their weaknesses. If you know nothing about AI, it’s good to try to catch up — but realize that if you invest your time into trying to develop an area of weakness, you’ll just be caught up to the average candidate and still significantly worse off than the best candidate out there.

That’s why it’s a much better use of time to go all in on your strengths. Your strengths are also usually the things you enjoy (because you’re good at them). By investing 100% into upleveling your existing strengths, you have a shot at being in the top 10, 5, or 1%. That’s a much more reliable way of protecting your career and becoming irreplaceable than taking some intro-to-AI course.

Do your research

Yarden: How do jobseekers find the remote job right for them?

Gillian: Do your research or use a remote work platform like Remote Talent. Companies struggle to clearly advertise their remote roles. Sometimes companies aren’t specific enough in their listing, or the platforms advertising their roles are restrictive — so they use the word “remote” as an all-encompassing word for any kind of role that doesn’t require 5 days in office. If you’re not careful, you will end up applying for positions that are not really ‌remote roles.

Remote Talent for the future of remote work

Yarden: What technology can influence the future of remote work?

Gillian: I believe wholeheartedly that there’s an incentive misalignment across the entire hiring-tech industry and its customers. It’s not controversial to believe that hiring is a broken industry that hasn’t improved dramatically with the introduction of technology.

Hiring-tech like Remote Talent is a great way for employers to connect with remote candidates so both parties find exactly what they are looking for.

Yarden: How will people’s attitudes toward remote work change?

Gillian: The shift toward remote work will create a more globally aware workforce. Employees will expect their employers to be attuned to international political dynamics, to acknowledge and offer support during significant global events, and to be empathetic toward the diverse situations affecting international teams.

Yarden: How should we all prepare for the future of remote work?

Gillian: Follow companies like Remote who are deeply entrenched in this space and committed to providing up-to-date information on remote work and culture.

Remote Talent is exactly the place for candidates and employers to connect about remote work opportunities. I’m excited for the future where employees can find their dream job, and where employers can find and hire a candidate in one click through our platforms. In that way, Remote Talent is a kind of solution that shapes the future of remote work.

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