Reader,
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In Part 1, I shared a story about a CEO who wanted to 2× his output without 2× headcount and realized his real constraint wasn’t talent. It was infrastructure.

So now let’s get tactical.

If you’re responsible for:

• Revenue
• Rep productivity
• Tech adoption
• and how work actually flows through your business

…this is the part that matters.

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1. Are you even AI/Automation-ready?

Before you buy anything, ask yourself:

• Do we have clear workflows in place?
• Do we know where time is leaking every week?
• Do we know what “good” looks like for a rep’s day?
• Do we have clean, usable data?
• Does someone actually own operations internally?

If those answers are fuzzy, tools won’t fix it.
You'll just be automating chaos.

2. Do you go with a Product or go Custom?

Here’s the mental model I use:

1. Do I need a data source I can’t replicate?

If the value comes from:

• A massive proprietary dataset
• A network you can’t rebuild
• A platform effect

You buy that.

Don't reinvent the wheel. Pay for the data layer.

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2. What’s the tradeoff between Time/Cost/Flexibility?

These are the three levers:

• Time: How fast do I need this live?
• Cost: What’s the real total cost (not just monthly)?
• Flexibility: How custom does this actually need to be?

Yes, you can build a perfectly tailored system.

But if it takes two full weeks of build time to get something a $99 tool can pretty much do today...

...you're losing 2 weeks of revenue.

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Remember what we said in Part 1?

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3. Interrogating Vendor Demos

Most demos are smoke & mirrors.

You need to know how to ask the right questions during demos if you want to gauge how well a tool will actually work for you.

Here are some to try out:

1. Walk me through how the product works and how it’s set up?
2. What part of this is logic vs automation vs AI?
3. What breaks when volume scales?
4. What does implementation actually require from my team?
5. What can’t this tool do?
6. How customizable are workflows, not just UI?
7. How is the data stored?
8. Who owns success post-sale?
9. What happens if my process changes in 6 months?

🚩 Red flag: If they can’t explain how the backend works, they don't know what they're selling.

Tech is only as good as how well it’s built. I’m not putting AI or automation into my environment unless I understand how the technology functions.

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4. Some Effective Tools On the Market in 2026

I had planned to compile my own list of the top AI-powered recruiting platforms across sourcing, business development but the PromptMates community, which focuses on AI adoption in talent acquisition, beat me to it.

They highlighted Stephen McGrath’s comprehensive list of modern AI and automated recruiting tools.

Basically, this category is expanding rapidly, and recruiters now have more off-the-shelf AI solutions than ever to enhance efficiency and impact:

The question isn’t “Which tools are best?”

It’s:

A few tools I like:

Now. What ever happened with that CEO?
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Let's break this down where we left off:

ZoomInfo vs Clay: Why "Unlimited" wasn't a good fit here

On paper, ZoomInfo looks unbeatable:

• Unlimited enrichment
• Direct access to data sources
• Ability to scrape signature lines (which is part of why their data is quality)

But this owner didn’t need unlimited.

Based on his team’s actual output, he expected closer to 400 contact lookups per month was needed.

That’s where Clay started to make more sense.

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Clay acts as a middle layer across ~12 data providers. Instead of being locked into one source, you can control where and how you pull data. It uses a “waterfall” model, going provider by provider until it finds a match.

Originally, we were told $300 would cover around 800 contacts per month.

But once we understood Clay’s pricing model—where mobile numbers cost the most and often require hitting multiple providers...we adjusted expectations to about 400–500 contacts for the same $300 🤯

Yes — ZoomInfo offers “unlimited.”
But unlimited only matters if your team can actually use unlimited.

He didn’t want to buy capacity his sales org couldn’t operationalize.

He wanted:

• Confirmed data across multiple sources
• A few hundred high-quality contacts per month
• Spend aligned with what his team could execute on

So even though Clay isn’t “infinite,” it matched his team’s real throughput, not some hypothetical max.

That’s why he chose Clay for a 1-month test, with a simple rule:

If it doesn’t feel right, we move to ZoomInfo.

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What He Learned About Clay

What worked:

• Waterfall enrichment across many providers
• Ability to scrape tables and integrate into CRM
• Flexibility to choose which sources to pull from

What frustrated him:

• Still working to understand how to return multiple provider info at once
• Some providers charge even when nothing is returned
• Billing and support issues (working on a Sunday and reached out to support only to see they aren’t open until 9am Monday. Although he did say the customer support team was able to resolve his issue quickly).

So the takeaway wasn’t “Clay is perfect.”
It was: Clay is powerful if you know how to control it.

Now what did he do with the BenAI product?

Build vs Buy?

Here’s where it gets even more interesting.

He looked at BenAI and said:

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But instead of buying, he spent the next week designing a custom CRM and AI workflows for his own team.

Why?

Because his sales + marketing org doesn’t truly operate in common stages...yet.
They have custom flows, custom handoffs, and very specific ways they divide work.

So he decided:

• Not to buy off the shelf
• But to build a system tailored exactly to how his teams market and sell

It took some time.
Would the BenAI product have been faster to implement? I'm not sure. Perhaps

But for him, the value was:

• Owning the logic
• Growing his technical muscle (we all know a tinkerer)
• Designing sales workflows that fit his org, not someone else’s template

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This tech leader ultimately realized this wasn’t about tools. It was about infrastructure design.

Once he started thinking that way, his options and decisions became much clearer.

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-Jaclyn