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

• 🎯 Why 50%+ of portfolio careerists land their first client through network

• 🔍 The 6-step playbook I would use if I were starting over from scratch

• ⚡️ Specific AI prompts and tools to research prospects, craft outreach, and generate winning proposals

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🏆️ Landing Your First Clients Using AI

Last week, I spoke on a Business Development for Fractionals panel for Portfolio Careers in Asia.

Yet sales has never come naturally to me as a builder. I remember feeling like an awkward fish out of water in my early discovery calls.

But like any skill, sales is a muscle.

By getting in reps each week, I learned to refine my technique. While I’m not a sales expert, I’ve learned a thing or two after doing 100’s of sales calls and closing 5-figure deals.

Here’s the gist:

I believe that sales skills are essential to build a portfolio career in 2025.

But the good news is that ANYONE can get good at sales. Plus, now you have many AI tools at your disposal to make it easier.

In this edition, I’m going to break down the strategies I would use if I were starting from scratch to get my first consulting clients (leveraging AI).

But first I want to cover something foundational:

🧠 The Wrong Mindset Will Cost You in 2025

In my early 20’s, I’m embarrassed to say I had a stereotypical view of sales - it’s all about convincing someone to say “yes” and buy.

Since then, I’ve learned the hard way how limiting this perspective is.

Sales is about deeply understanding your clients challenges and guiding them to the right solution - for them. The best salespeople I know are world-class problem solvers and trusted advisors.

Shifting this mindset changed everything for me.

This is especially important in a highly competitive niche market like fractional work, so you can stand out. According to the Frak report, there were 120,000 fractional leaders in 2024, up from 60,000 fractionals in 2022. Wild numbers.

Here are 6 strategies to getting your first clients using AI:

1/ Find people in your network 🔍

In our research, over 50% of portfolio careerists got their first client by tapping their network and referrals.

That’s why I recommend starting with audit of your existing work, school, and social relationships. Write down 20-30 people that fit your ideal client profile (or adjacent).

If you’re not sure who you know, export your Linkedin contacts or use AI:

👉️ Try this:

• Use Happenstance (free) to conduct an AI-powered search across your Linkedin and Gmail contacts.

• Let’s say I’m a Fractional CFO for early-stage climate tech startups. I can search for “seed stage climate tech startups” and get the following results:

2/ Research the signals ⚡️ 

Next up is researching company profiles. This helps you tailor your positioning to be crystal clear on why specific clients should chose your services.

👉️ Try this:

Use Perplexity to get a snapshot of the company priorities

✍️ Use this prompt:

Depends on your function / industry, but I recommend seeing if these triggers apply:

• Preparing for a fundraise or recently raised funds

• Team is quite junior and needs senior guidance

• Founder feeling overwhelmed / current setup is unsustainable

• Need a full-time CXO but can’t wait 6 months to hire

• Entering a new market and missing on-the-ground intel

I’ve seen fractionals or consultants get leads in all the scenarios above. For example, fractional CFOs I know get many of their inbound requests when early-stage startups are preparing to fundraise. So if I were a fractional CFO, I would track fundraising activity closely.

For triggers not discoverable online, I would ask someone who works at the company or knows their staff well if possible.

Ultimately, these insights can help you position your services effectively.

3/ Send outreach messages 📬️ 

Now that you have your contacts, prioritize the contacts for a 1:1 call, email, or Linkedin message.

Start with people who can back your work (like former colleagues) and are connected.

My client, a VP of Growth, recently reached out to her former boss - who was excited to work with her again. A few weeks later, she kicked off a new consulting project.

Write a short blurb asking for the feedback, NOT if they’re interested in using your services. This is more effective in my experience.

✍️ Try this prompt in Claude:

The output is decent starting point, but you’ll want to refine it before you send.

Bonus Tactic: Another one of my clients, a Head of Content for a big creator, successfully closed her first consulting client by sliding into their Linkedin DMs with a Loom video breakdown of their content strategy. Smart move. Let me know if you give this a shot!

4/ Announce to your network 📣 

One low-hanging fruit is to broadcast to your Linkedin network that you’ve opened up shop.

You can do this with a Linkedin post OR adding a new job to your work history. The latter typically gets more reach.

My client, a Fractional COO for SMBs, recently announced her service offering on Linkedin and immediately got a couple of fresh leads from her network.

But if you just HATE writing Linkedin posts, then here’s an alternative:

✍️ Try this:

1. Record yourself talking using a voice note with ChatGPT

   1. Include details like what clients you serve, your offer/service, social proof or examples of your work, how people can learn more, yadda yadda

2. Copy-paste the transcript into Every Spiral (free for 20 runs) to generate a Linkedin post in your style

The cooked up post won’t be perfect, but you can edit it then publish.

NOTE: Still want more leads? Here’s 11 client acquisition channels. I’ll also continue sharing under-the-radar techniques I hear about in this newsletter.

5/ Run your discovery call 🗣️ 

Congrats, now hopefully you’ve setup up some initial conversations - let’s call them “discovery calls.”

Here is the rough call structure I like to use:

• Introduce yourself and set the meeting goal

• Ask a lot of questions and listen carefully to their motivations, desired outcomes, pain points, and barriers (hint: this is the MOST important part!)

• Synthesize and summarize what you’re hearing back to the potential client (e.g. “I’m hearing you have [goal] but you’re getting stuck in [insert barrier]”)

• Guide your potential client through how you can help, breaking down into milestones (e.g. “we can help you with [milestone #1] - the reason why we’d do that is to help you move past [pain #1]…”)

• Pause for questions and clarifications

• Wrap up and discuss next steps (e.g. “are you ready to move forward?”)

Now let’s help you prepare your script quickly:

✍️ Try this in ChatGPT:

6/ Send your proposal 💼 

After your discovery call, it’s time to translate your client insights into a compelling offer proposal.

In informal cases, I simply send a follow-up email (or WA text) with bullets on the milestones we discussed, program, investment, and how to get started. And that’s been sufficient to close some deals.

When I need a more structured proposal:

✍️ Try this in ChatGPT:

After you cook the proposal, edit and share it as an attachment to your email. Boom! 💥 

Takeaways

Getting started with sales in portfolio careers can be hard, especially if you come from a non-sales professional background.

Fortunately, you can significantly accelerate the process with AI:

1. Find people in your network

2. Research the signals

3. Send outreach messages

4. Announce to your network

5. Run your discovery call

6. Send your proposal

I hope you land clients this summer using these techniques.

Thanks for reading! What did you think of this piece? Reply and let me know your thoughts.

💎 Last Week’s Gems

🌶️ Hot Takes on Fractional Work - 5 spicy ones from Taylor Crane, Founder of Fractional Jobs.

📈 WSJ reports that tech employment fell by around 214,000 jobs in April, but also a survey more than 250 technology leaders by Robert Half found that 65% said they were increasing the number of contract hires this year.

💪 Why high performers should make assertions. Wes Kao writes about the difference between insights, suggestions, and assertions.

✨From Our Community

• Next Community Call: June 5, 2025 5pm PST / 8am SGT → Register Here

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Meet Melanie Palapuz

Melanie Palapuz is a product designer @ WPP and consultant. She’s based in London, UK.

How would you describe what you do to someone outside of your industry?
I enjoy uncovering human insights and designing meaningful solutions for them. Business value is customer value, and at the end of the day we're all human—we want to belong, we want to feel included, and we want to be understood. I believe the future of design will be more mission-driven, inclusive, and empowering.

What triggered your interest in exploring the portfolio path?
I believe economic empowerment is real empowerment. Having diverse income streams that are owned by you alone can lead to a more fulfilling and sovereign life.

What’s your current portfolio career mix?

1. Product management / design job in fintech

2. Consulting

3. Investing portfolio

What’s one specific change you’ve made to live life more on your own terms?
My faith is important to me, and lately I've been leaning into it more—I do believe that God gave each of us skills and a vision for a reason, and it's up to us to achieve it and execute on it in this lifetime.

What advice would you give to someone starting a portfolio career?
At the end of the day, a career should serve you and the life you want to live, not the other way around. Use the money you earn to buy yourself time and location freedom, and to live life on your own terms.

What’s a fun fact about you?
Used to be a DJ, hope to get back into it again and maybe host some small apartment dinner parties :) 🎶 Song of the season: Listen here

How can people connect with you?

• LinkedIn

• Design Portfolio

• Email: [email protected]

P.S. Did you enjoy this spotlight? Hit reply and let me know—or suggest someone else we should feature next!