🐧 Building a remote Upwork agency | Ken Leaver

INSIDE: Ex-CEO of Groupon Ukraine to Founder of Bangkok-Based Virtual Agency
October 22, 2023

How do you start a virtual agency? Enter Ken Leaver, founder of agency End Game.

In this edition, he is kindly sharing some of the lessons he’s learned along the way in building a virtual agency.

Today in 10 minutes or less, you’ll learn:

  • 🚀 How Ken Went From London Strategy Consulting to CEO of Groupon Ukraine to Bangkok-Based Virtual Agency Founder
  • 🤔 ELI10: What is a Virtual Agency? Who is a Good Fit for Starting One?
  • 💼 How Ken Hires & Onboards His Remote Team and the Exact System and Tools He Uses
  • 🤯 Why Ken Cut Down His Interview Process By 80% and Swears By Upwork Contractors


💪 Go from stuck to breakthrough in your career transition

❌ Feeling stuck in your current role?
❌ No idea how to make your career change?
❌ Dreamed of working abroad, but don’t know where to start?

I know how it feels.

Waking up on Sunday and feeling that rush of anxiety that Monday is around the corner.

I’ve personally made 4 major career changes in my life, each time shocking my system:

✅ 2014: Marketer → Product manager
✅ 2019: Moved from US to SEA, started coaching business
✅ 2020: PM → Product leader
✅ 2023: Product advisor, started Money Abroad

I love working with clients who—like me—feel restless in the status quo and seek to make bold career changes.

For example, I’ve worked with new moms getting back in the workforce, non-profit workers breaking into tech, and a US techie transitioning to a unicorn in Mexico.

As a coach, I help you with navigating your transition end-to-end.

From strategizing and clarifying your end destination to executing the job search process itself, together we’ll help you accelerate your growth.

Sounds intriguing? Book a free discovery call now.

🧑‍💻 Building a remote Upwork agency | Ken Leaver

Ken is a Solopreneur who operates his own ‘Virtual Upwork’ agency, End Game, that utilizes freelancers to perform projects in tech, content creation, and SEO.

He has held senior product positions at companies like Lazada, Wayfair and Pomelo Fashion. And contracted for a range of companies like Branded, Ozon, Shipper, Wayfair, Rainforest Life, Yandex and others.

He’s part entrepreneur, part product guy, and part writer. But mostly just a “structure & process freak.”

Tell us about your career journey from consulting to startup founder to tech agency owner.

I graduated Cornell back in 1999 and back then the sexy thing to do was either investment banking or strategy consulting. I chose consulting.

Consulting took me from Boston to Tokyo to Kuala Lumpur to London to Moscow. Over seven years I met some amazing folks and got to the point that I could do PowerPoint in my sleep.

But in 2007, I had reached the point where I was supposed to sell work.. and I realized I’d hit my limit. I just couldn’t sell things with six-figure price tags. It was too much of a step up from my previous selling experience of selling lemonade on the corner as a kid. LOL

So in 2008 as the Russian economy was tanking along with the rest of the world… I moved to work for my client, Visa Inc. And did the whole corporate thing for a few years... managing first thier Russian acquiring business and then their regional Issuing Products business.

But when a friend came in early 2011 and said to me, “Ken… I want you to run Groupon in Ukraine,” I was like “Hell Yeah! This is my chance to become famous!” At the time… Groupon was pretty sexy.

And Groupon was an amazing ride. We grew from a ~10 person office to over 100 employees…. and something like 50x’d the revenue. But as they say…. all good things eventually end. And in 2012 as we were losing money still, I was asked to start cutting the team.

Groupon would continue to decline in the ensuing decade…. so in hindsight it was a wise decision to move to the next shiny object ‘startups’. In 2013 I joined the leading startup accelerator in Ukraine, “Eastlabs”, which was funded by one of the wealthiest businessmen in the country, Victor Pinchuk.

Ever since moving to the region I’d always wanted to try working for an ‘oligarch’ so finally I got my chance. And while that part was far less sexy than i thought (ie. I never even met Victor haha), the accelerator part was actually pretty awesome.

We invested in ~16 companies and several success stories were created like Preply who I believe is valued around $400m or so today. But in late 2013 the first war in Ukraine started and the economy started to tank. I felt like it was time to take a break from the region.

So with my pregnant wife, we moved to Ho Chi Minh City in early 2014 and I began working for Lazada. I was supposed to be on the commercial side, but due to some major health issues that were screwing with my concentration… I asked to switch to “product”. At the time, I’d never even heard of product management before… but I figured these sleepy-looking tech guys must be easy to compete with. So I dove in.

At first, I felt like a fish out of water with all these engineers walking around. What the hell were they even talking about? But in time I got to really enjoy it and moved up the ranks. Eventually making it to SVP Product in charge of all operations, marketplace and finance products for Lazada (~50% of all tech).

Since that time, product has always been a part of what I do and I really love it. Particularly eCommerce product. Following Lazada, I did stints as a Director of Product for Wayfair (the US furniture eCom) and as the Head of Product for Pomelo Fashion. And have also contracted for numerous large ecom players like Ozon, Yandex, Branded, Shipper, etc.

That takes me to today where I run my own ‘virtual agency’ providing a mix of product and other tech services.

Explain how a tech agency works to a 10-year old. Who is a good fit for starting a tech agency and why?

Hmmm how does an agency work…. Clients find me and ask me to do things like build a product (eg. a website, a new SAAS), or make content (like Youtube videos, newsletters), or SEO and I do it. But I’m not an employee, rather I just work as a contractor for them.

And I often bring in other contractors to help me. I call it a ‘virtual agency’ because these contractors I have help me are not my employees. Rather I source them from either Upwork or Fiverr and the client typically pays for them directly with no markup from me.

But then I get paid either a retainer or performance-based commission (eg. for clicks if its a SEO project). I really like this model because it’s very transparent to the client and our objectives are tightly aligned. I don’t make money unless they get customers/traffic/etc.

In terms of who is a good fit for running an agency, I would say that you need to be a ‘hustler’. Someone who just loves what they do, loves to work a lot, and wants to control their own destiny. You also gotta have the organizational skills to keep many balls in the air because you’re always mixing business development of new clients with implementing your existing ones.

Shopify site developed by ~6 freelancers from Upwork & Fiverr hired in 2 days.

How have you hired and onboarded your agency’s remote team? One remote hiring challenge I’ve heard of is evaluating quality of work—how did you navigate this problem?

So I’ve onboarded 100+ folks from Upwork and Fiverr onto my various teams over the past three years. And I have a pretty standard process where I add them to my Clickup space, my Notion space, Slack and have them join our daily standups.

When I onboard my team on Upwork, I usually just give them a small scope of work that takes a week or so.. and I make it clear that we’re still feeling each other out. During that week, I assign them tasks and see how quickly they adopt my Clickup-based organizational system:

  • Do they complete the tasks correctly?
  • Do they comment when they need help?
  • Do they respond to my comments in a timely way?

These are all things I look for.

And in general, my experience is that I only keep about one out of every three contractors that I onboard. The rest I let go within the first few weeks. But without any dramatic firing. Rather I just don’t create another Upwork order and we go our separate ways.

How have you managed your remote team? What systems, processes, and/or tools have you used to streamline operations? (for example: with communicating across time zones)

I am a die hard fan of Clickup.

Here’s how I set it up for my remote team:

  • Kanban. I have a very specific Kanban-based approach that I use with it. Each person has tasks written up in Clickup with a priority and a due date. Then they update the card with the work they did as comments.
  • Communication standards. I also give them a SOP (in Notion) on communication guidelines for the team. For example everyone needs to clear their Clickup and Slack notifications at least 2x per day. And since I follow each Clickup card, I know if they haven’t and remind them.
  • Time allocation matches billing. Another key is that I’m using Upwork folks who allocate their time to the Clickup tasks that they do. And this time allocation is expected to align to what they bill in Clickup. So I’m only paying for their productive time and don’t really care what they do as long as they get their tasks done. Plus, they know that I review how much time they allocated to each task and call out where I think it took too long. So that keeps them on their toes.

With this simple approach I feel like the teams I’ve worked in have really nailed this whole remote team, asynchronous work thing. I think I literally get 2-3x more done with the same resources now than I did pre-2021 when I first started this approach.

Fintech app built in Bubble in 6 weeks with Upwork team hired in 3 days

What mistakes have you made while managing remote teams? What would you have done differently?

At the beginning, I’d spend a lot of time interviewing contractors from Upwork before I hired them. Thinking that I’d choose much better people this way.

Then I realized this is bogus. Who I thought would be good when I talked to them on a 30-minute call was often completely different from who turned out to truly be good.

So now I only speak to them for 5-10 minutes and check a few basic things before giving them a small scope to work on. Within a week I know more about how good they are than the most exhaustive interview processes I’ve ever been apart of (including my strategy consulting days where we often had 4-5 rounds).

What counterintuitive or lesser-known advice would you give to people looking to build remote teams?

Go down the rabbit hole of using a project management system like Clickup with a TON of discipline. With my teams I operate under the rule of “if it takes more than 20 minutes than it should be captured as a Clickup task”. I find this to be so critical on being very clear with my team on what they should be spending time on. They never wonder what to do next and I never wonder what they are doing.

Use mostly contractors from platforms like Upwork and not employees. You see a lot of the mistrust in remote work and it comes in my view because managers feel like they get more value from the team if they’re sitting in front of them. But if you only pay for their productive time on a platform like Upwork you no longer care how they spent their day. You only care that they got their tasks done and that the time billed to them was fair.

  • Plus, I’ve consistently found that working with contractors allows you to vet people much faster. A wrong full-time hire will often set you back six months or more, whereas I correct my Upwork hiring mistakes in a week.
  • And contractors are far far less political. Why? Because they don’t have a strong vested interest in being involved in their client’s politics. And as a person who hates politics I find this to be a massive benefit. We are now all working for a single goal with no side agendas. Which is often not the case with employees.

8) Where can we go to learn more about you?

🌐 Beyond your borders

🇸🇬 Driving in Singapore now costs $158,004 before even buying a car (link)

🌏️ This is the no. 1 fastest-growing digital nomad hotspot in the world (link)

🪖 How to invest during times of war (link)

📆 How I can help

That’s all for today!

Whenever you’re ready, here’s how I can help you:

1. Side Hustle Crash Course (free) - Click here to receive my free, 5-day course teaching you the foundations of building a service-based side hustle.

2. Remote Side Hustle Launchpad - Join my cohort in Fall 2024 alongside high-performers. This is the system I used to earn over $100,000 from my side hustles taking 10 hours/week.

3. US expat tax service - Get personalized help on your tax returns from a US expat tax professional.

4. Promote yourself to 6,000+ high-performers by sponsoring my newsletter.

For daily insights, follow me on Linkedin and X (@dexteryz)

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Dexter Zhuang

Dexter is the founder of Money Abroad, an online education platform helping high-performers design their independent money path. He has 10+ years of experience building products and teams at public companies (Dropbox) and scaling startups (Xendit) across the US, Asia, and Latin America. His work has been featured in global outlets like Business Insider, CBS, US News & World Report, and Tech in Asia. He graduated from Dartmouth College.

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