How do you onboard your automation clients, create the roadmap, and set expectations for retainer clients?
I start with a kickoff call where I deliver quick wins to minimize buyer's remorse, and I always take payment upfront before any work begins - never considering a client 'onboard' until the money is in my account. After receiving payment, I create a detailed proposal that serves as both a sales document and a roadmap. Roughly 60% of the proposal outlines the client's problems, demonstrating my understanding from any prior small project; about 20% covers the proposed solution; the remaining 20% discusses logistics, principally compensation. I typically pitch a large monthly fee - recently moving from $6,900 to around $12,000-$12,300 - and often add a revenue-share component to align incentives, inspired by the idea that sharing upside makes both parties more comfortable and can lead to more money. I discuss performance-based versus flat pricing, noting that beginners should lean performance-based, intermediates may go flat, and experts often return to performance-based because they have confidence in delivering results. Once the client agrees and pays, I invite them to a kickoff call to set communication expectations: I'm highly reachable via Slack (within 15 minutes) and hold daily office hours from 12 p.m. to 2 p.m. PT, plus a weekly strategy session. I ask clients to commit to the same recurring time each week for at least 50 out of 52 weeks, emphasizing consistency so they take the calls seriously and see ongoing value. During each meeting I review wins from the past week, outline what I'll do next, and address any questions or fires, ensuring I always show up with something tangible to justify the retainer. I then follow the roadmap, checking off the 45-plus tasks in order, and optionally sync with the client's project-management system (though I've moved away from using my own ClickUp board as the single source of truth). I also note that other agencies like DesignJoy use shared boards, but I prefer bringing a quick note of wins and next steps to each meeting.
I build new systems rather than just maintain one, because you’d quickly run out of high‑ROI systems to apply to their business. The ROI from something like Lead‑en automation can be massive, which justifies the recurring payment, but if the retainer were only for maintenance of a single system you’d worry about endless revisions. I don’t think it’s wrong to charge a retainer even when the ongoing work is near zero, because the systems I build produce value independently—you don’t have to constantly watch over them. It’s like hiring an emergency plumber who charges $500 for a 30‑second fix; the fee reflects the expertise built over years, not just the time spent on the job. So the ongoing work doesn’t have to be zero for you to get paid, but you must continuously provide value—perhaps through a system that runs cold email autonomously, for example. What I provide on a monthly retainer includes: unlimited maintenance on all systems we’ve built together; a 15‑minute availability window each day (12 p.m. to 2 p.m. PT) where you can ask me any question and I’ll reply within about 15 minutes; a weekly strategy call (30‑45 minutes) where I slot into your business and tell you exactly what you need to do to make more money, essentially building a roadmap for the coming week; I also often create a big monthly roadmap at the start of the month or include a proposal with a list of 50 things I want to do when we begin working together, which I follow unless I provide a separate monthly roadmap; unlimited new project requests—you can make as many requests as you want and I’ll add them to my queue, though realistically I usually complete about one new project per week because I have templates and blueprints for most things, so I’m not spending eight hours a day fulfilling a $7,000‑a‑month client; there’s a lot of perceived value in this, comparable to what clients would pay for a standalone maintenance package, Q&A and training for the team, a weekly strategy call, or consultation at my hourly rate (around $800). Instead of building every project myself, I increasingly describe exactly what the system should look like or provide SOPs for your team to build it with their own tools, so I’m not a single point of failure and your team develops the skills to build these automations as well.
After hiring around 40-50 people for my agency, I've realized I prefer to hire last. The common advice to delegate everything comes from a time when technology couldn't handle much of the work, but today technology gives us leverage, so you can realistically wait until you're making around $50k/month before your first hire instead of $15-20k. Hiring early is often just a band-aid for deeper problems—if you're under $25k/month the issue is usually your systems, not a lack of manpower. Focus on building systems that reduce the work needed to fulfill: automate repetitive tasks like onboarding emails, scheduling calls, and problem-solving via email; design productized offers that take half the effort to deliver (e.g., a form that auto-generates a campaign, scrapes leads, and follows up); create scalable sales flows (a discovery/closing call batched together, a proposal, and automated follow-ups that stop when a deal isn't worth the effort). Make client management discrete—set a daily 8 a.m. five-minute template update instead of letting clients interrupt you on WhatsApp all day. Hiring early means giving up a large share of profit (e.g., a $5k salary is half of your profit at 50% margins) plus management costs and risk; it's better to wait until revenue is higher so the hire is a smaller fraction of margin. I pay a flat salary plus a clear, trackable bonus—staff log it themselves and add it to their invoice—avoiding profit-share or rev-share because they misalign incentives and add overhead. Finally, I only care about deliverables: if someone is intelligent and ambitious they can build their own systems to finish work in fewer hours, and as long as the output is good I don't track hours.
Retainers replace unpredictable hourly billing with a recurring, prepaid service model. For example, if you previously billed 20 hours at $50/hour ($1,000), a retainer might lock in those 20 hours at a discounted rate of $45/hour ($900) paid upfront. This gives you guaranteed income and lets you schedule work knowing exactly how many hours each client will need each month, eliminating the feast‑or‑famine swings of hourly work. The real power of a retainer lies in what you bundle with the core service. Instead of selling just the automation build, you add items that make the offer a no‑brainer for the client: a regular strategy call (e.g., a 45‑minute weekly meeting); unlimited maintenance: you fix any API glitches, server outages, or platform issues at no extra charge; an availability guarantee, such as promising to respond on Slack within 15 minutes between 12 p.m. and 2 p.m. Monday‑through‑Friday; emergency Q&A or training sessions where the client can ask “How do I update this?” and get immediate help; and access to any resources or tools you’ve built for them. These extras increase the client’s perceived value and satisfaction, improve retention, and generate referrals, while they don’t scale linearly with your time — so you can serve more clients without a proportional increase in workload. From a utilization standpoint, clients often use fewer hours than they pay for (e.g., 18 of the 20 contracted hours). You still receive the full retainer payment, meaning your effective hourly rate remains at your baseline ($50/hour) while you enjoy predictable income. Over a six‑month period, a $1,000‑per‑month retainer yields $6,000 lifetime value; after subtracting acquisition costs (say $150 per client), your net profit jumps from $850 on a one‑time $1,000 deal to $5,850 — a margin increase from roughly 85 % to 97.5 %. Working with repeat clients also lets you understand their business deeper, deliver more nuanced solutions, and earn more referrals. Finally, because you’re building automation systems, the value you deliver isn’t tied to your personal time: a system like my cold‑email setup that generated 23 leads last month continues to produce results even when I’m not actively working on it, adding another layer of leverage to the retainer model.
I think we should start by clarifying terminology: I wouldn’t consider someone a client until they’ve paid money—or at least committed to paying for something, like a software subscription. Until money changes hands or an agreement is signed, it’s not a real client. Many people think a deal is closed when the prospect says yes, but it’s not truly closed until they sign or, better yet, pay the invoice. Saying yes is different from actually paying you. You said you started automation in November, learned it in two months, and since January you’ve only got two clients in the process of closing. Over roughly 60–70 days, if you’d done a daily outreach minimum—say 10 personalized Loom videos a day via Upwork, DMs, Instagram, X, etc.—you’d have contacted about 700 people. Yet only two showed interest, which is about 0.3% (2 out of 700), or roughly 1 in 350. That’s extremely low; to get one ‘yes’ you’d need to hear roughly 349 ‘nos’. If you’d done consistent, reliable outreach using the mechanisms I show in Maker School and on my channel (daily Loom videos, etc.), even if you were terrible at it, it would be statistically unlikely to get so few results. Typical response rates are around 2%, which would be about eight times better than what you’re seeing. So you likely reached out to far fewer people—maybe around 80 total, or about one per day. To improve, first be very clear about what ‘closed’ means—wait for payment or a signed agreement. Second, set a clear daily outreach minimum, like sending 10 customized Loom videos a day on platforms such as Upwork, Instagram, X, or via DM. Third, standardize your sales process: use a repeatable roadmap (like my ‘Roadmap to $25k a Month with Automation’) that funnels prospects into a meeting, then a sales call, then a detailed proposal or scope of work, and follow the same steps each time. Doing this builds infrastructure you can iterate on—run it for 10 clients, tweak, run another 10, and you’ll see conversion rates improve. That’s what I’d do if I were in your shoes.