What would you do to close one or two retainer design clients in the next couple of months, and where should I focus and spend money?
To land one or two retainer design clients in two months with a 20% call‑to‑client conversion, you need 5‑10 calls. Over 60 days that’s roughly one call every 6‑12 days. Aim for one call every 12 days: with a 1% booking rate you’d contact about 100 people in 6 days, or ~15 people per day. That’s doable with the free manual outreach method—send cold emails or Loom videos on LinkedIn, X, Instagram, TikTok, etc. You don’t need money or elaborate planning; just commit to taking action.
Propose the retainer immediately, explaining that long-term retainers allow higher quality work and deeper system knowledge, leading to better results. During the project, learn everything about the client's business and ask questions. Deliver the project with a customized video that documents the system and suggests further opportunities, leveraging reciprocity after over-delivering. Then pitch the retainer consultatively, focusing on the relationship and the client's potential growth, which makes them more likely to agree to hear you out.
To close a client with limited proposals send custom Loom videos. They let you practice and deliver your value proposition without the cost or stress of live calls—effectively giving you free sales‑rep experience. Plus personalized outreach maximizes the return on every dollar you spend on Upwork connects; if someone watches your video you want the highest chance they'll convert. Also always use your real face on Upwork because clients want to work with a genuine person not an avatar.
The most suitable niches and products or services to build for clients that allow a monthly recurring relationship are those that can be delivered as ongoing systems. In a nutshell, focus on things like cold‑email systems, CRM management, or voice‑agent solutions—any service that you can justify a monthly retainer for. For example, with a cold‑email system you could send 10 000 leads a month, provide a 45‑minute strategy session, a monthly report, and end‑to‑end campaign management with nurturing, and charge around $3 270 per month plus $98 per lead. With CRM management you could offer 40 hours of new‑build work plus unlimited maintenance on old systems, plus Slack availability, and price it at roughly $4 000–$4 120 per month (assuming a $120 hourly rate and a 20 % discount). For voice‑agent services you could bundle a weekly strategy call, a weekly report, call‑analysis, and up to 100 hours of agent uptime, pricing it around $2 180 per month. These three retainer models aren’t the only ones, but they’re quick to set up and sell.
He explains that a retainer works by bundling a set number of hours (e.g., 20 hours per month) and selling them upfront at a discounted rate, which stabilizes income and removes the variability of hourly billing. For example, at $120/hour, 20 hours would be $2,400; offering a discount to $100/hour makes it a $2,000 monthly retainer. The client gets guaranteed availability and easier planning, while you gain predictable revenue. You can then add value‑adds—monthly reports, weekly calls, standardized Slack availability—that increase perceived value without consuming extra billable time, effectively raising your effective hourly rate. The retainer shifts the sale from pure time to outcomes and ongoing benefits.