Getting your first few customers is hard. Especially if you’re pre-launch and almost nobody has heard of your company, in an era when AI-enabled products are being shipped and distributed in ever-increasing numbers.

That’s why I often recommend that founders build a “Roster of Advisors” as a means to finding initial customers, especially when selling into mid-market businesses. These are practitioners in your target market who bring you closer to the customer: they offer perspective, feedback and some percentage of them end up becoming your first few users and champions.

It’s a method I’ve seen work again and again with early-stage teams. I've helped about 20 companies use some version of this, and while it's not a silver bullet, it’s one of the more reliable ways to make real progress in those early days.

To build this roster, try cold outbound. This forces clarity in your messaging and your target prospect when you are sitting in front of an email sequence hour after hour, week after week. And a way to increase the open rate and response rate of your outreach is to ask for expertise, not time to view a demo, or even harder, buy a product. You’re not asking someone to sit through a sales pitch—they’re not a buyer yet and you’ve hardly built anything to sell. You’re inviting them to lend their expertise, shape something new, and (ideally) get something out of it themselves.

What This Is—and What It’s Not

This isn’t a formal board of advisors you’re announcing on LinkedIn or putting on your pitch deck. And it’s definitely not a collection of celebrity names that’ll impress investors but have little to do with your actual customer.

In some ways, it’s the exact opposite. It’s a loose collection of thoughtful people in the industry you (eventually) are selling to, who have strong opinions about how they want technology to work for them, and are willing to help someone shaping a vision of solving their problem.

When This Approach Works Best

This strategy works best when:

• You're going after SMB or mid-market customers
• Your product is in the early idea or prototype stage
• Your deal size is modest (say, under $100K ACV)

It’s not really the right approach if you’re selling a seven-figure platform to Fortune 500 CFOs. But if you’re trying to reach the head of operations at a 300-person manufacturing company, or the director of a regional chain of healthcare clinics, this is often an effective way in.

Start by Defining a Very Specific Customer Profile

First, determine who you’re trying to reach. Not “mid-sized companies,” but something much more specific. For example:

“Home health agencies with 100–500 caregivers, headquartered in the Southeastern U.S., still using paper-based scheduling.”

That level of specificity helps you filter who you’re looking for, what language to use in outreach, and which examples will resonate.

You will broaden later, when you tweak your VC pitch deck to indicate your TAM is enormous. But that kind of targeting works against you at this stage, when your advisors (and prospective design partners) care more about whether you understand their business, and can solve their problem, than whether you can also solve an adjacent partner’s problem.

Build a Target List

Once you’ve nailed your ideal customer profile (ICP), it’s time to put together a list of people who fit that profile. There are a few ways to go about it:

• Hire a freelancer on Upwork to scrape company names and executives in your category
• Use tools like LinkedIn Sales Navigator or Apollo to identify individuals with relevant titles
• Prioritize people who are likely to use or directly benefit from your product—not just execs at the top of the org chart

Launch and iterate this list. In other words, don’t wait to have 500 names to start calling and emailing--a few dozen high-signal names is a good start. Ask the people who interact with you substantially to recommend 2 - 3 other people they know who might be a good match.

Reach Out with a Clear, Respectful Ask

When you begin outreach, make it clear you’re not selling something. You’re inviting them to help shape something early.

Here’s a structure that tends to work well:

Subject: “Equity Compensation for Expertise — Startup building [X]”

Hi [First Name],

I’m building a startup focused on [brief description of the specific problem]

We’re bringing together a group of advisors who know this space well. In exchange for light involvement—a few calls over the next few months—we’re offering small equity grants.

You came up in our research as someone with the kind of perspective we’re hoping to learn from, based on [insert specific about their profile that is relevant].

Do any of the below times work for a 20 minute call?

[Date - time]

[Date - time]

Thanks so much!

Keep it short, honest, and specific. People appreciate a clear ask, especially when it’s about expertise—not a veiled sales attempt.

Follow up with 2 - 5 additional emails and LinkedIn notes. Be “politely persistent” so it’s clear you’re thoughtful and thorough, and make sure the subsequent messages continue to emphasize that there is something specific in their profile that appeals to you, and that you aren’t just reaching out to any random person.

Start your outreach to those close to you with whom you can make the most mistakes, and who will forgive you when you mispronounce an important company name, or don’t know an acronym that’s critical in the industry. As you learn more about the industry and the specific pain points, only then reach out to the real influencers and folks who aren’t connected to you, those with whom you may only have one shot to get it right.

Run the Calls Like You’re a Student, Not a Seller

Once someone agrees to a call, your job is to listen.

Start by explaining what you’re building and why you reached out. Then shift quickly to asking them how they currently handle the problem you’re trying to solve. What’s working? What’s broken? What’s missing?

As a professional conversationalist, I’ve learned over the years that most people like to talk about their work if you give them the space to do so. Ask a handful of open-ended questions (with specific diction, indicating you understand their area), and let them go. You’ll learn so much from these calls, such that in a week’s time of ~5-10 calls you’ll be far up the learning curve and be even more credible in the next week’s calls —about their workflows, buying behavior, budget cycles and team dynamics. Stuff you wouldn’t get from a product forum or blog post.

If the conversation goes well and this person has the kind of insight that could help shape your product, let them know you’d love to keep in touch in a more structured way—as part of an informal advisory group.

Offer Light Compensation

Structure a light-touch advisor contract that offers small amounts of cash or equity in exchange for time and feedback.

Some guidelines:

• Equity: 10–25 basis points (bps), usually vesting over 1–2 years with no cliff
• Cash (optional): Some folks appreciate a nominal hourly rate ($100–$200/hour) for time-intensive conversations
• Time: Make clear you’re asking for occasional feedback, not ongoing operational help

Many of the startups I worked with on this offer cash or equity, but only in cases where someone’s time is truly valuable, they are a lynchpin in their industry, and they expect some form of compensation. Oftentimes the promise of compensation opens the door, but the genuine interest in helping a technologist solve a problem keeps an advisor coming back, for free.

Keep the Cadence Manageable

There’s no need to calendar weekly meetings or force a Slack group. You don’t need to brand this initiative. It’s fine if these advisors never meet each other, and there’s no formal announcement. The relationship should feel light touch but genuine.

Every few weeks, you might send a short update:

“Hey, here’s the first version of the onboarding flow—would love your take if you have five minutes.”



or



“We’re rethinking pricing—curious how you’d evaluate these tiers.”

Think of it as an ongoing conversation, not a scheduled obligation. The best advisors will lean in naturally when they care about the product and see how it’s evolving.

Develop Your Roster of Advisors Timeline

In the very early days of company-building, I recommend building a roster of up to ~30 of these advisors, whom you should accumulate over the course of 3 - 4 months. This list is the ‘bottom of the funnel’, meaning you’ve probably reached out to 1,000, and spoken to upwards of a hundred, before landing on this group of fine folks to remain in contact with.

That also means you’ll have numerous data- and anecdata-points to inform your Minimum Viable Product (MVP) definition, and a large number of folks to engage with once you’ve built something. And you’ll also have a much larger group than 50 of folks to keep ‘in the know’ (in a marketing drip campaign of sorts) as your company building process develops. Track who you’ve spoken to, what they’ve given input on, and when you last followed up. A spreadsheet style CRM of your advisors and conversations is sufficient.

Advisors Validate ICP and What to Build in Your MVP

Over time, these advisors will give you a wealth of knowledge about your industry, the problems it has, and where your potential technology would be the most beneficial. To understand this breadth, you need to have hundreds of conversations with scores of practitioners. As you do this, you should track several attributes associated with your advisors:

1. Whether they are ‘potential customers’ vs. ‘feedback partners’ (the latter because their organization doesn’t have the exact pain you’re solving for, or otherwise can’t buy)
2. How influential they are (1 - 5 scale)
3. Specific characteristics associated with the industry you’re building for. For instance, if you’re selling into home health clinics you might track skilled home care vs. non-medical home care vs. palliative care facilities.
4. Size of company

The more you build up this roster with heterogeneity, the more you can learn - about what to build, whose pain points are strongest, and thus how to get commercial traction quickly.

Advisors Should Become First Customers

If someone has helped you think through early product decisions, chances are they’ll be one of the first to try your product when it’s ready. They understand what you’re solving. They trust you. They’re invested in seeing it work.

Aim to make three to five of your early advisors your first few customers. Sometimes, they’ll even help drive the internal decision at their company. Other times, they’ll refer you to peers at other organizations.

That first ask can seem hard in theory, but in practice once you’ve built a relationship with an advisor, and they’ve understood and appreciated your approach to solving the problem they have, asking them directly if they will enter into a commercial arrangement is a logical next step. Start with ‘what would you pay for this, once it’s built’ and when they give you a range, discount it and ask if they could guarantee that, presuming you build what you’ve outlined.

You Can Sell the Product Before It’s Built

To put it plainly - it is ok to enter into a contractual arrangement with someone to deliver a product that you have not yet built. Keep the specs general (describing the problem the product will solve, not exactly how it’s architected) to allow yourself wiggle room, and use softening language like ‘Company will make every available effort to deliver Beta Product by XYZ date’. Give yourself ample time to build something (naturally you’ll be working closely with your technical cofounder or engineering team) and break down payment so you have some money paid up front (likely ≤ 25%) and the rest upon delivery of the product.

Through all this, be generous with updates. Even if they don’t become customers, people like seeing the impact they’ve had. It builds goodwill—and sometimes gets them back in commercial conversations later.

If you’ve done this or are thinking about it, I’d love to hear how it’s going (jdimento@baincapital.com). I’m always curious how different teams approach this—and what’s worked (or not worked) along the way.