Should I accept an agency offer to create systems and do direct response ads, or continue seeking cold email clients via Upwork, given I have no experience and want to stay focused on cold email?
If you're early in your career and need experience and to pay down debt, take every opportunity—including agency work—to build skills and cash flow. Once you're earning $10–$20k/month as a solo freelancer, saying yes to everything spreads you thin and prevents skill accumulation; you'll plateau. At that point, niche down to one or two core offerings so your revenue can keep growing. Early stage: say yes to everything. Later stage: focus and specialize.
Upwork works well for beginners who lack sales‑marketing experience—it’s a simple paid‑access to a pool of people who already want what you sell, so you don’t need to be a strong salesperson. Cold email gives you access to the whole world, but your ability to explain, justify, and sell the problem becomes the big differentiator. Cold email is typically more scalable and makes more money over time than Upwork, though Upwork is easier to start with. I actually use both in tandem.
Yes—Upwork is the straightest line to your first customer when you’ve never sold anything before. It lets you get into conversations, learn basic sales, and earn an initial return on investment while paying down client‑management and skill debt you didn’t know you had. However, relying on Upwork long‑term is a crutch because most projects are custom, forcing you to rebuild the wheel each time and making templated delivery impossible. After you’ve cleared that debt, transition to more scalable outbound methods like cold email. Only after a couple of months do you begin exploring scalable inbound or social‑media approaches. The early phase is strictly Upwork‑focused to bootstrap the business.
Most clients on Upwork don’t want to work with agencies. I recommend not using Upwork as a primary agency growth channel; treat it as a way to get an initial foothold while you’re still freelancing. When you’re selling yourself, you want the client to feel they’re hiring you, not an agency. Avoid agency language on your profile—use “founder” if you like, and bring up any consultants only during calls after you’ve secured the project. Start as a freelancer, deliver a high‑quality first project, get a great review, then gradually introduce others or a consultant on later projects. Don’t say you’ll hand the work off to an agency; keep the work yourself initially. In short, don’t label yourself as an agency on Upwork—position yourself as an automation specialist or similar, because Upwork users dislike the word “agency.”
Great question. I should make it abundantly clear that when you have a hammer, everything looks like a nail. My hammer is cold email, so I try to solve every problem with it. Cold email isn’t always the most effective marketing method, but it’s like a video game where you keep playing the main character because you’re best at it. I would definitely use cold email. I’d start by pitching these SMA agencies. I’d go to Apollo and filter for 1‑11 staff, looking for digital marketing, digital agency, or creative agency. I’d use the OR operator to pull as many as possible—probably a list of 30 k to 50 k in the United States alone. Then I’d blast out my offer with the software, giving a free demo. I’d position it as if I’d read the person’s whole life story and built the software just for them. I’d mention that I’ve been following what they’re doing at [their company] and that I used to run a digital marketing agency (maybe I still do). I’d share that I’m suffering from XYZ problem and that this software is the solution I came up with. I’d want to put it in front of them to see if it has value. I’m 100 % confident that running their clients through my system will generate outsized returns, so much that I’m willing to guarantee it and give it away for free just to hear their thoughts. If they’re open to a quick call, we could jump on it. I’d approach this at the higher‑agency level, positioning myself as an agency owner talking to agency owners, not as a SaaS person trying to sell something. I’d get on as many calls as possible and frame them almost as partnerships: give them a trial of the software, let them solve their current problems with it, then use that feedback to improve the software faster and better. Once I have a ready‑to‑go version, I’d charge premium prices. And yes, I’d go straight cold email, starting with agencies because they tend to have more money than SMBs.