Interview: Connor Gillivan On How To Win New Clients & Writing Better Proposals

What skills should you develop to become a better freelancer?

What should you do to get access to an exclusive freelancing platform?

How can you keep your clients happy to build long-term relationships?

In this interview, I discuss all these matters and more with Connor Gillivan.

Connor Gillivan is the CMO and the co-founder of Freeeup, a new freelancing platform that features the 1% of the best freelancers.

Connor has been doing business since the age of 16. His first business was a landscaping service, which he provided to everyone in his neighborhood. Then he went on to sell products on Amazon, worth over $25 million in sales.

Connor is also a fellow freelancer. Before starting work at Freeeup, he’s worked as a freelancer to help eCommerce businesses build successful online stores.

During the interview, he shared a lot of valuable advice and his own personal experiences of working with clients and freelancers. Let’s dive in.

Freeeup website claims it only accepts the top 1% of the freelancers from all the applications you receive. Why do you use such a strict vetting process?

My business partner, Nathan Hirsch, and I spent years hiring freelancers from other large marketplaces like Upwork and Fiverr. We ended up spending hours and time posting projects, sifting through applicants, interviewing, and trying to find the best freelancer. We were frustrated with how much time we were spending vetting and we ended up running into a lot of turnovers.

When we created FreeeUp, we wanted to build a better way for business owners. FreeeUp only accepts the top 1% of freelance applicants so that business owners know they are getting introduced to someone that has the experience, knows how to communicate, and is passionate about building their freelancing business.

For freelancers, we also wanted to improve the process. We saw freelancers competing for every project being posted on the larger platforms and it led to decreased rates and wasted time when the freelancer didn’t land the gig. With only accepting the top 1% of applicants, those freelancers have much less competition and can get introduced to quality clients faster.

What’s this vetting process looks like? And what do you look for in a freelancer when accepting an application?

So the vetting process is three stages.

Stage 1: The freelancer submits an application that provides their resume/CV, online portfolios, examples of their work, a typing speed test, an internet speed test, and answers to why they’re interested in joining and how they run their freelance business.

A certain percentage of people are then invited to a 1 on 1 interview with someone from our team.

Stage 2: The freelancer has a 1 on 1 interview where we really focus on asking them more questions about their skills, attitude, and communication. We’re looking for freelancers that have a clear expertise within a given skill set.

For example, they can talk intelligently about managing social media accounts and strategies if that is the skill they are looking to offer. For attitude, we look for freelancers that are passionate about the services that they’re offering and growing their freelance business.

Finally, we look for freelancers that can communicate at a high level with clients. Communication is one of the biggest issues that clients run into…we don’t want that to be a problem in the FreeeUp Marketplace.

Again, a certain percentage of people make it past the 1 on 1 interview and are invited to the final stage.

Stage 3: The freelancer takes a test on communication best practices showing that they are prepared to handle working with clients at a high level.

The top 1% are filtered out through this entire process.

How would you suggest a freelancer prepare before joining a top-tier site like Freeeup?

(1) Experience. Have past experience freelancing and working with clients. Have the ability to talk about your skills and how they help businesses grow. Have stories that you can share about past clients you’ve worked with and the specific skill sets that set you apart as a freelancer.

(2) Communication. Have specific communication channels that you know how to use at a high level. Skype, Slack, Trello, email, Viber, etc. Whatever it is, make sure that you have routines of how to check in and provide updates to clients. The more communicative you can be, the better.

(3) Attitude. Be ready to show that you are passionate about the work you’re performing and that you are taking your freelance career seriously. Clients want to work with people that are excited about their skill set and are up to date with what’s going on in the industry. The more enthusiasm and positivity that you have, the better.

If you lack in any of these areas, make sure to find a mentor who has done it before. Ask them questions. Get advice. And turn their past experiences into ways to improve your own freelancing efforts.

I’m sure you must have worked with plenty of freelancers when developing Freeeup and your other businesses. How do you identify the best freelancers to hire?

When looking for new freelancers to hire, I am always on the lookout for individuals that hit on the three main areas of being a reliable freelancer.

(1) Skills- They have years of experience in the skill set. They have worked with many clients in the past with good track records. And they can answer difficult questions with regards to their skill set that they say they have.

(2) Attitude- I look for freelancers that have a real passion for being a freelancer, running their business, and working with interesting clients. If I get the sense that the freelancer is overworked or not excited about waking up every day, I keep looking. I want someone that is positive, excited to work, and wants to really grow together.

(3) Communication- I always ask lots of questions to freelancers about how they communicate with clients and how they’ve done it successfully in the past. If I’m interviewing with someone and they are very slow to respond, that is an immediate red flag.

When freelancers fit into all of these three categories, I know that they are a great candidate to work with.

What’s the most terrible experience you’ve ever had with a freelancer?

So, back when my business partner, Nathan, and I started hiring freelancers from around the world, we ran into a situation where we hired two sisters to work on the customer service of our growing eCommerce company.

We put them both through our interview and testing process and they seemed to be an amazing fit for what we were looking for. They had the experience, they seemed outgoing, and they spoke strong English. They were working with us for a number of weeks and then one of our in-house team members noticed something odd with how they were signing on and off.

It turns out that they were taking each other’s shifts (they were twins so it was hard to notice) and not telling us which led to issues in setting them up and having them work on different times for the business. Trust is one of the biggest factors with us as business owners and they were not giving us the full story.

It led us to move in another direction and try to find another set of individuals to join the customer service team. It was a terrible experience because of the time and effort we had put into interviewing and hiring them only to end up back at step 1 looking for new people.

One of the biggest questions I get from beginning freelancers is how to write a winning proposal when pitching for a job. Having been on both sides as a freelancer and a client, do you have any tips these freelancers could use?

When pitching for a project with a new client, it’s best practice for the freelancer to first fully understand the project that the client is looking to hire for. If possible, set up a 10-15 minute chat with the client to learn more about the details of the project.

And ask questions about the (1) deadline (2) estimated budget (3) client expectations and (4) hours each day/week. The freelancer should know exactly what the client is looking for with the project once they are finished with this quick chat.

From there, it’s best practice to display how the freelancer’s skills and past experience can relate to the project. Address the details that were received and give examples of how they would approach the project for the client.

When it comes to communication best practices, make sure to ask the client “how do you prefer to be communicated with?” They may say email, Skype, WhatsApp, etc.

As a freelancer, listen to what they say and take it seriously. In general, it’s best practice for freelancers to check in when they start work for a client, check out with a short summary once they finish for the day, and send email updates as necessary so that the client is always up to speed with what the freelancer is achieving.

The more communication the better.

What are your thoughts on the future of work? Especially with the advancements in the AI technologies, do you think freelancing would still be relevant in 2030?

Yes, I’m a strong believer in the freelance and gig economy growing over the next 20-30 years. I see freelancing thriving into a major aspect of the world workforce over the next 10-15 years and then continuing to mature from there.

Right now in the US, freelancers make up over 30% of the workforce already and it’s expected that freelancers will be over 50% of the economy within the next 10 years.

From my experience working with freelancers from all over the world, I see a similar trend happening as well. More and more professionals are seeing the opportunity to offer their skills through the Internet to companies around the world.

Professionals are valuing flexibility and the ability to create their own income at a higher level than past generations. Similarly, companies are also seeing hiring freelancers as a more viable option than they did 10 years ago. It just makes sense.

The future of freelancing is bright and it’s an amazing time to get into the industry. Building your expertise and reputation today could make a major impact on your income opportunities in the next 5 to 10 years.


Thanks, Connor for sharing all the amazing advise. Be sure to check out his blog and you can find him on Twitter too.