Strategic Roadmap: Building a Remote Dream Team for Your Startup

Before even thinking of hiring anyone, you should figure out the organizational structure of your future team. Analyze the work and map out the responsibilities of every role.

Start with the founders. Understand your partner’s strengths and find the right people to reinforce each other’s weak spots.

Another question is where to find talent. Having an in-house local team is a luxury for most early-stage startups. Hiring remotely and offshore is the way to go, especially, since the eastern seaboard now offers highly qualified experts.

Read on to find out more about hiring a remote team for a startup in the USA.

Where to search candidates for your remote team

If it’s a technical person you are in the market for, take advice from Bryan Helmig, CTO and сo-founder at Zapier:

We are looking through projects, we are looking through LinkedIn, and just find people who we think are interesting. We try to email them and try to learn a little bit about them. We don’t spam anyone.

We generally find someone like “Wow, this person worked on this library, they worked on this language, they did this – that’s really impressive”.

And, therefore, I’ll email them and talk to them. We also find candidates on Hacker News, on GitHub, on Twitter, really any place where people congregate. We find StackOverflow pretty solid in this regard.

These are excellent pieces of advice from Brian, and on top of that you can always post your open positions on remote-friendly job boards:

• We Work Remotely is your number one platform for seeking explicitly remote experts.

• Flex Jobs rivals We Work Remotely for the number one spot in remote candidate search. They have been building remote teams since 2007.

• Remote.co is an exclusively remote job board with a simple interface praised by CNN, Entrepreneur, Inc., and many others.

• Remote OK is a remote job board trusted by AWS, Microsoft, YCombinator, Shopify, and other top brands.

• Remotive is a trusted platform that has helped remote companies hire top tech talent since 2014.

• No Desk helps companies from new startups to the largest distributed enterprises to build their remote teams.

• Glassdoor is currently the most popular job search platform. It’s a household name and the first place people go to when seeking a new job.

• Indeed rivals Glassdoor in its popularity. Together they are the two leading job-seeking platforms on the market.

• Blind claims to provide access to top talent from companies such as Google, Meta, Amazon, and more.

• Hired.com grants you access to a curated pool of experienced tech talent from engineers, DevOps, product designers, product managers, data analysts, and more.

• Karat (previously TripleByte) provides pre-screened technical candidates and accompanying hiring services.

• Rainmakers is a marketplace for hiring sales and marketing experts.

Use applicant tracking systems

Managing prospects in a small spreadsheet or Trello board may work well when you are screening 5-10 candidates a week. Once you start scaling your sourcing process, you will require a more sophisticated solution.

The hiring process often includes stages such as recruiter and HR screening, multiple-stage interviews, technical screens, offer negotiations, and onboarding. To keep everything on track in such a complex process, a wise decision would be to deploy an applicant tracking system (ATS).

Greenhouse and Lever are currently the two platforms battling for the place at the top of the market having a variety of useful features. But you can always check to see if any of the other top applicant tracking systems match your individual needs.

An ATS can help you out with a variety of hiring issues. For instance, if your number of offers is way below the large number of interviews you hold, you can determine if it’s merely a sourcing problem or if you have a weak evaluation process.

Interview pointers for founders

• Prepare Thoughtful Questions: Develop a set of questions that not only assess the candidate's skills but also delve into their personality, work ethic, and cultural fit within your startup.

• Focus on Cultural Fit: Gauge how well the candidate aligns with your company culture. Ask about their work style preferences, teamwork approach, and values to ensure a cohesive fit.

• Highlight Company Vision: Emphasize your startup's vision, goals, and values during the interview. Discuss how the candidate might contribute to these objectives and share enthusiasm about the company's future.

• Evaluate Problem-Solving Skills: Pose scenarios or challenges related to your startup's industry or the role itself. Assess the candidate's approach, creativity, and critical thinking skills in solving these problems.

• Assess Adaptability: Startups often require employees to wear multiple hats. Inquire about their adaptability to evolving roles and tasks within a dynamic work environment.

• Prioritize Communication Skills: Evaluate their communication skills, especially in a remote or distributed work setting. Ask about their preferred communication methods and how they ensure clarity when working remotely.

• Discuss Past Achievements: Inquire about their past achievements or projects relevant to the role. This helps gauge their level of expertise and accomplishments in similar contexts.

• Clarify Expectations: Clearly outline the expectations for the role, including performance metrics, growth opportunities, and the impact the candidate could make within the company.

• Invite Questions: Encourage candidates to ask questions about your startup, the team dynamics, future plans, or any concerns they might have. This demonstrates their interest and engagement.

Take some notes from experienced leaders on how to pick exceptional people for the job:

Clarissa Shen, COO of Q Bio, a technology company operating at the intersection of AI, Physics, and Biology, suggests adding this simple entry to your interview questionnaire:

What’s something new you’ve learned recently?

Clarissa explains why it’s such a valuable insight saying she is on the lookout for lifelong students yearning for more knowledge and experience: “I’m listening for an innate sense of curiosity as well as what motivates and interests them.”

Zainab Ghadiyali, former Product Lead at Airbnb, recommends asking your candidates:

What are 1-2 questions you always ask your team members in one-on-one meetings, and why?

Zainab says it helps him understand whether a manager is good at motivating people and building strong relationships with the team.

Liz Fosslien, Head of Storytelling for Team Anywhere at Atlassian, shares one of her favorite questions:

What ritual or practice have you found to be most effective for helping your team connect and collaborate?

What Liz is trying to determine here is whether a candidate has a working management playbook that will gain them the ability to make quick-fire and spot-on decisions. Having a repeatable recipe allows the manager to avoid mistakes in the future.

Gokul Rajaram, product leader at DoorDash, thinks it’s important for executives to be involved in the product-building process directly. To figure this out during the interview, he proposes to ask candidates:

Tell me about a time when you delved into significant detail and got your hands dirty.

There are a million things you can ask a prospect. Try to think of questions that would reveal how they would manage their day-to-day tasks, as well as those that allow them to describe their personality and demonstrate their soft skills.

Legally hiring remote employees within the USA

Hiring remotely spares you of the burden of maintaining your office and on-site workspace. In addition, you are not bound by your locale and have the opportunity to attract talent from all over the US, across different states.

The most important step in hiring remotely is signing a remote worker agreement that regulates your relationship with the new employee. Here’s a great template you can use (just make sure you consult with your lawyer on this as well):

Remote Employee Agreement Template

This freedom of recruiting talent from border to border, however, does come with its own stipulations. When you hire out-of-state, the employee needs to abide by the employment laws and regulations of the state where they perform the work.

Five Key Factors to Consider When Hiring Remote Employees Across States

To embark on recruiting out-of-state remote workers successfully, grasp a fundamental rule: adherence to the local laws where your employee resides, not where your company headquarters operates. As the work transpires in these diverse states, aligning with their employment regulations is paramount. Here’s a breakdown of the crucial considerations:

1. Application and Salary Inquiries

• Ensure your application process aligns with state regulations, refraining from probing into restricted areas such as criminal backgrounds or salary histories. Abide by basic queries or seek advice to construct compliant application and interview procedures.

2. Payroll Compliance and Taxation

• Complying with payroll laws is critical to avoid legal penalties. Understand the Fair Labor Standards Act (FLSA) and delve into state-specific payroll requirements. Accurate payment methods and tax adherence are vital to prevent costly errors.

3. Employee Welfare and Compensation

• Consult state laws concerning breaks, time off, unemployment taxes, and workers’ compensation. Formulate clear guidelines for employees, covering job duties, work hours, and equipment provisions to mitigate risks related to overtime or injuries.

4. Legal Documentation Dissemination

• Inform remote employees about their rights, adjusting your approach to meet remote-friendly alternatives. Understand state variations in document distribution—some allow digital copies while others require hard copies, ensuring compliance and accessibility.

5. Privacy and Data Security

• Establish robust data protection standards, including non-disclosure agreements and secure file transfer protocols. Safeguarding sensitive information from breaches or unauthorized access is crucial for your business’s financial security.

To make the process easier, many founders choose to enroll in the services of a payroll provider that acts as their representative within the state and manages all the intricacies of withholding and remitting taxes. There are plenty of payroll services out there, with ADP TotalSource, Gusto, SurePayroll, and Paychex standing at the top of the market. Make sure you pick the right platform that suits your particular needs.

Legally hiring people from abroad

Each country has its own jurisdictions, employment regulations, and tax laws. In order to build an offshore remote team for your startup, you will have to comply with all of them. How do you do that?

There are two distinctive ways of legally hiring people from abroad:

1. Set up an established business entity. This is simple but costly. All you have to do is set up a legal entity in a country where you want to hire personnel. It will allow you to stay compliant with local laws while also pursuing payroll tax deductions.

2. Use employer-of-record services. You can always take advantage of platforms like Deel to hire employees on your behalf without the extra hassle of dealing across jurisdictions. You can indirectly hire and set up payroll for employees across various countries and stay fully compliant.

Establishing a smooth workflow for a remote tech team

Once you hire the right people, it’s your responsibility to keep the dream team’s spirit alive and well. To maintain an efficient workflow within a geographically decentralized team, you’ll need to set up the following infrastructure:

• Shared workspace: With tools such as Jira, Trello, Asana, and Notion you can organize your team, share important data and files, assign tasks, set goals, break them down into key milestones, and track your progress.

• Cloud data storage: using a cloud-based shared document platform like Dropbox, Google Drive, or Confluence is essential for everyone to have access to the files they need.

• Corporate calendar: a calendar allows you to coordinate important launches, communicate deadlines, and share schedules to be in the loop on teammate availability.

• Real-time communication: Modern chat and messenger apps such as Slack or Discord will allow you to freely communicate and maintain a strong connection with your remote team.

• Face-to-face meetups: An online meeting app like Zoom is great for having daily stand-ups and discussions. Of course, you can go hipster-style and use the metaverse or online game setup to have fun while you’re at it.

Jason Fried, Co-Founder and CEO at 37signals, recommends making the most of a remote work setup:

Working remotely is not working locally.

Don’t try to make one the other. If you have meetings all day at the office, don’t simply simulate those meetings via video. This is an opportunity not to have those meetings. Write it up instead, and disseminate the information that way. Let people absorb it on their own time. Protect their time and attention. Improve the way you communicate.

Remote team aspects founders often miss

Not many founders even consider hiring their top priority, spending less than a third of their time on talent acquisition. That’s why there are many things that can potentially go wrong. To make sure you don’t end up with a half-baked team, we list a few pointers here:

Do not skip candidate interviews

Understandably, you will have your hands full with other startup and product development tasks. However, hiring is one of the key ingredients of a successful venture, so spend some time with it.

Keith Rabois, general partner at Founders Fund and previously an executive with top brands like PayPal, LinkedIn, Yelp, Xoom, YouTube, Lyft, AirBnB, and Quora, believes that founders should take part in interviews with every candidate until the startup tops 500 employees.

Don’t hire mediocre people

Take it from Apple’s playbook and never compromise or settle for a mediocre team. Having a mediocre person do the job is much worse than being late on your product launch or losing a lucrative investment.

You are aiming for a product that’s going to break through the competition and win the market. It’s an exceptional product that requires the work of exceptional minds.

Celebrate and cherish success

It’s important to show your remote team players that what they’re doing makes an impact. They need to know their achievements matter. And also, it’s a part of corporate culture: you have to organize these events and keep people engaged because the truth is: Bored People Quit.

Something as simple as a public congratulation can do the trick. But it’s always fun to make it interesting and throw in some perks for the frontrunners of your startup.

Lead your remote team by example

One of the most important things for a remote team is mutual trust. You can’t spend all of the time micromanaging and being a control freak. Most times you need to rely on your team to deliver on their objectives.

So how do you do that? You lead by example. Show them you hold true to the core principles of your corporate culture and identity. Communicate, collaborate, and openly exchange ideas. Trust others when it comes to them having more experience than you.

There’s a difference between management and leadership. Most experts won’t need a manager to get things done. But your team still relies on your vision and ability to steer them in the right direction.

If you're seeking further insights and advice from seasoned founders, we highly recommend delving into "Best Practices for Managing a Remote Team" by Y Combinator.

Conclusion

The important thing in hiring a team for your startup is not to rush things. Creating the right chemistry takes time and your results depend on the choices you’ve made early on.

Hiring exceptional talent, growing at pace, and making the best of the resources you currently have. That is probably the shortest path to fruitful product development and an eventful startup evolution.

Maintain a healthy relationship with your team players, stay true to your cultural values, and lead your startup by example. Having built a strong foundation, you will be able to steadily and efficiently grow your company to enterprise scale.