Client Acquisition and Proposals
From outreach to proposals to closing deals. Use AI at every step of winning new business, writing proposals that convert, and building a client pipeline.
The Proposal That Won the Project
In the previous lesson, we explored marketing and content creation for one. Now let’s build on that foundation. A freelance web developer sent two proposals in the same week. The first listed his services, hourly rate, and timeline. It read like a menu: here’s what you can order.
The second started with “After looking at your current site, I noticed your contact form converts about 2% of visitors. The industry average for your sector is 5-7%. Here’s how I’d close that gap.” It went on to outline a specific plan with projected outcomes.
The first prospect ghosted him. The second signed the contract the same day and became a long-term client.
Same developer. Different proposal approach. AI helps you create the second type every time.
What You’ll Learn
By the end of this lesson, you’ll know how to do personalized outreach, write proposals that win, follow up without being annoying, and build a sustainable client acquisition system.
The Solopreneur Sales Funnel
Client acquisition has stages. AI helps at each one:
AWARENESS → INTEREST → CONSIDERATION → DECISION → CLIENT
Content Outreach Discovery Proposal Onboarding
Follow-up Call Follow-up Welcome
Most solopreneurs focus only on awareness (marketing) and skip everything else. Then they wonder why visibility doesn’t convert to revenue. This lesson fills in the middle.
Smart Outreach with AI
Cold outreach doesn’t have to feel cold. AI helps you personalize at scale:
AI: "Help me write a personalized outreach message.
I'm a [your niche].
The prospect is [name/company/role].
Their business: [What they do, what you know about them]
Something specific I noticed: [A problem, opportunity,
or detail from their website/social media/public info]
Write a short outreach message (under 150 words) that:
1. References the specific thing I noticed (shows I did research)
2. Connects it to a problem I can solve
3. Offers one concrete insight or suggestion (gives value upfront)
4. Ends with a low-pressure next step (not 'buy my services')
Tone: Helpful peer, not salesperson. Like a colleague
pointing out something useful."
Example output:
“Hi Sarah,
I was looking at GreenLeaf Tea’s website and noticed your product pages don’t have customer reviews visible – they’re buried three clicks deep. For e-commerce in the specialty food space, visible reviews on product pages typically increase conversion by 15-20%.
I specialize in e-commerce UX for artisan food brands, and I’ve helped three similar companies increase their product page conversion just by restructuring how social proof is displayed.
Would it be useful if I sent over a quick sketch of how your chai collection page could look with reviews integrated? No obligation – I just think there’s a quick win sitting there.
Best, [Name]”
Quick Check
When was the last time you reached out to a potential client proactively? If you’re waiting for clients to find you, you’re leaving revenue on the table. Outreach is a learnable skill, and AI makes it much easier.
The Discovery Call Framework
When a prospect is interested, the discovery call determines whether you’re a fit:
AI: "Create a discovery call framework for a [your niche]
solopreneur.
The call should:
1. Build rapport (2 minutes)
2. Understand their situation (5 minutes)
3. Identify their goals and pain points (5 minutes)
4. Present how I can help (3 minutes)
5. Discuss timeline and budget (3 minutes)
6. Define next steps (2 minutes)
For each section, give me:
- The questions to ask
- What to listen for
- Red flags that this isn't a good fit
- How to transition to the next section
Total call time: ~20 minutes.
Include a pre-call research checklist (what to look up
about the prospect before the call)."
Post-call summary prompt:
AI: "I just had a discovery call. Here are my notes:
[Paste your rough notes]
Create a structured summary with:
1. Client needs (what they want to achieve)
2. Current situation (what's not working)
3. Budget indication (if discussed)
4. Timeline (when they need it)
5. Decision factors (what matters most to them)
6. Red flags (any concerns)
7. Recommended next step
8. Proposed scope outline (for my proposal)"
Writing Proposals That Win
Here’s where most solopreneurs lose deals – not because of skill, but because of presentation:
AI: "Write a project proposal for this potential client.
Client: [Name/company]
Their problem: [What they need solved]
Their goals: [What success looks like to them]
My proposed solution: [What I'll do]
Timeline: [How long it'll take]
Investment: [Your price]
Proposal structure:
1. UNDERSTANDING YOUR SITUATION (show I listened -- 2-3 sentences
restating their problem in their words)
2. THE OPPORTUNITY (what's possible if this is solved --
specific outcomes)
3. MY APPROACH (how I'll solve it -- 3-5 phases or steps)
4. WHAT YOU GET (specific deliverables, clearly listed)
5. TIMELINE (with milestones)
6. INVESTMENT (price with brief justification)
7. ABOUT ME (2-3 sentences of relevant credibility)
8. NEXT STEPS (exactly what happens if they say yes)
Rules:
- Focus on THEIR outcomes, not my process
- Use specific numbers where possible
- Keep it to 1-2 pages maximum
- Confident, not arrogant
- Include a clear expiration date (creates urgency)"
Proposal tips from experience:
- Send within 24 hours of the discovery call (speed wins)
- Reference specific things they said during the call
- Price based on value delivered, not hours spent
- Include exactly one option (too many choices = no choice)
- Make the “yes” path easy: one clear next step
Follow-Up Sequences
Most deals are won in the follow-up, not the initial pitch:
AI: "Create a follow-up sequence for after I send a proposal.
Context: I sent a proposal to [type of client] for
[type of project] at [price point].
Create 3 follow-up messages:
Follow-up 1 (Day 3):
- Check in casually
- Add one piece of value (relevant insight, article,
or additional idea for their project)
- Don't ask "did you see my proposal?" directly
Follow-up 2 (Day 7):
- Reference a result I achieved for a similar client
- Offer to hop on a quick call if they have questions
- Create gentle urgency (timeline, availability)
Follow-up 3 (Day 14):
- Graceful last attempt
- Leave the door open
- Offer an alternative (smaller scope, different timeline)
Tone: Helpful and confident, never desperate.
Each message should be under 100 words."
Quick Check
How many proposals have you sent in the last month that you didn’t follow up on? Each one is a potential deal sitting in someone’s inbox, forgotten not because they said no, but because they got busy.
Building a Client Pipeline
Consistent client acquisition means never running dry:
AI: "Help me build a weekly client acquisition routine.
My current situation:
- I need [number] clients at a time
- My average project lasts [duration]
- My target monthly revenue: [amount]
Create a weekly routine that includes:
Monday: [acquisition activities]
Tuesday-Thursday: [client work + what to do in gaps]
Friday: [pipeline review and planning]
For each day, specify:
- Exact activities and time required
- Number of outreach messages to send
- Content to create/publish
- Follow-ups to send
- Pipeline tracking updates
The goal: never be scrambling for clients. Always have
prospects at different stages of the funnel."
Tracking Your Pipeline
A simple system beats a complex one you don’t use:
AI: "Create a simple client pipeline tracker for a solopreneur.
Stages:
1. PROSPECT (identified, not contacted yet)
2. CONTACTED (outreach sent)
3. RESPONDED (they replied)
4. DISCOVERY (call scheduled or completed)
5. PROPOSED (proposal sent)
6. WON / LOST
Columns:
- Name/Company
- Date entered this stage
- Source (how I found them)
- Project type
- Estimated value
- Next action
- Notes
I'll update this weekly. Keep it simple enough to
manage in a spreadsheet. Include formulas or rules
for when to follow up based on time in each stage."
Exercise: Build Your Acquisition System
This week, complete these steps:
- Identify 5 prospects who fit your ideal client profile
- Research each one (website, social media, recent news)
- Use AI to craft personalized outreach for each
- Send the outreach messages
- Set up your pipeline tracker
- Draft a proposal template you can customize for future use
- Create your follow-up sequence templates
This system, maintained weekly, ensures you never run out of prospects.
Key Takeaways
- Personalized outreach converts dramatically better than generic messages
- Proposals should focus on client outcomes, not your services or credentials
- Follow up 3 times after sending a proposal – most deals are won in the follow-up
- Discovery calls have a structure; AI helps you prepare and debrief
- Build a weekly acquisition routine so you’re never scrambling for work
- Track your pipeline in a simple system and review it weekly
- Speed matters: send proposals within 24 hours of discovery calls
Next lesson: Operations and admin automation – tackling the invoicing, scheduling, and admin work that steals your billable hours.
Knowledge Check
Complete the quiz above first
Lesson completed!