Running an Upwork Agency - Frequently Asked Questions

Running a Successful Upwork Agency: Lessons, Challenges, and Key Insights

We started to work as an agency on Upwork in the summer of 2013, have earned Top Rated status, several “Best Agency” and “Freelancer” awards, and more than 1 million dollars since then. So, we look like people who know how to run an agency on Upwork (though sometimes we do not feel this way at all :)

Upwork invites us from time to time as speakers at their events, and people often ask us the same questions. So, we decided to collect those questions and answer them in this post.

Is Running an Agency the Right Path for You?

First of all, this path is not for everyone. Establishing your own company is the first step, and, like any business, it requires a significant amount of time and energy. Moreover, it brings its risks and difficulties, and your work might become less stable and secure.

Another challenge is responsibility. You’re accountable not only for providing your employees with a steady income and interesting tasks, but also for delivering excellent results to clients on time.

Before starting an agency, decide if you are ready for these challenges.

How to Get Started

• Find a partner – You need at least two people to form a team. Ideally, cover both technical and communication skills.
• Secure a project – Make sure it’s something your team can do well. Your first feedbacks are crucial.

Misconceptions About Agency Life

Some people believe that being an entrepreneur means earning more money and having more free time. It might be true about money (but not always!), but free time is rare.

As the agency grows, more effort is needed. To avoid burnout, utilise tools and processes to delegate and automate tasks. Good managers are also key.

Balancing Workload Is the Hardest Part

The biggest challenge is workload balance. You need a steady flow of projects, enough to keep people busy but not so many that they become overloaded.

Based on our experience, it’s better to have someone focused on business development from the outset to avoid a swing-like situation: too much work with not enough people, or too many people and no work.

Building the Right Team

You can find great professionals on Upwork, but top profiles don’t always mean top performance.

• Give a test task or start with a small project.
• Consider hiring a full-time Sales or Marketing Assistant who understands your values and internal processes.

Our Values and Internal Setup

Our core values are honesty and transparency. All our agency members are real people with their own Upwork accounts and work directly with clients.

We operate as a company. Most of our team works from the office and was not familiar with Upwork before joining. A few remote team members came from Upwork and now work with us full-time.

Communication with Clients

Everyone on our team speaks English fluently and typically communicates directly with the client.

Project Coordinators focus on analysis, planning, and delivery, not just passing messages.

Leading Your Team

• Set an example of strong communication and ownership.
• Discuss tasks thoroughly.
• Create rules around workflows and client communication.
• Have monthly 1-on-1s with each team member for feedback and development.

Getting Projects

We usually apply from my account or recommend a team member. We always clarify that we’re a company.

The time to land a new project varies. It used to take up to two weeks, but now it’s longer due to higher competition and our niche focus.

Writing Winning Proposals

There are many proposal tips on the Upwork blog. Here are mine:

• Customise your message.
• Read the job post carefully.
• Write clearly.
• If you can help or advise the client, do it upfront.

Test different approaches and track what works best.

Dealing with Difficult Clients

You can’t change people, but you can change your attitude.

• Stay calm and try to understand the client’s priorities and fears.
• Communicate effectively, manage expectations, and strive for win-win resolutions.

Our Personal Principles

• Be honest and transparent.
• Do what you promised.
• Be professional and always improve.
• Communicate well, sometimes it's more important than the code.
• Admit mistakes and fix them.
• Respect clients.
• Be a good leader and take responsibility.
• Value your reputation, it’s more important than money.

We hope these tips are helpful. If you have any additional questions, please don't hesitate to contact us here.