Forecasting AI, Automation, and Audiences in B2B

Interview with Doug Jackson, Fractional CRO

WOLF'S BYTE

1/9/20244 min read

Welcome to Wolf’s Byte: Sales and Marketing for B2B Tech, where I interview industry experts for insights on creating content that drives sales.

I interviewed seasoned fractional chief revenue officer (fCRO) Doug Jackson, who gives his take on how AI and automation are changing the lead generation and sales game.

Our discussion went into what no longer works, what’s changed, and ends on what to put your stake in as audience expectations and technology evolve.

More specifically, Doug gives insights on:

Prospecting
Fake social
Personalization
Marketing process and strategy
Data tracking
Split-testing and optimization
CTAs

If you’d like some perspective to help orient your thinking as we move into 2024, keep reading.

We’ll also include some weird scary AI art because, why not?

Changing Prospecting Methods

Our discussion started with me mentioning that my old prospecting methods weren’t working. Instead of sending out the usual 50+ emails that would inevitably land a trial project, I gave up after about 200 (and no trial projects).

I was using the same script, qualifying companies and individuals the same way, but I was using automation software to speed up the process.

The database of verified emails, in particular, helped cut out a lot of the time I used to spend finding and verifying emails manually.

AI-driven automation tools like Reply.io greatly expand outreach capabilities but, they’ve created a problem as well.

The individuals who previously weren’t being flooded with spam emails, are now.

Worse, the messages themselves are increasingly AI-generated, with little human oversight, making them generic and irrelevant spam.

The result is that, beyond my own personal cold outreach, engagement rates are dwindling as audiences tire of impersonal mass-generated messages.

I asked Doug how can we recalibrate our approach to ensure our messages stand out?

His answer?

We need to infuse our communications with unique insights and expert knowledge to capture attention. It's not about being verbose; it's about delivering precise, targeted messages that resonate.

Rise of Fake Accounts and Apprehension

Fake accounts and AI-driven chatbots have also flooded the market, making everyone (including potential customers) even more wary and guarded than before

All of this inauthentic interaction is causing a ripple effect — prompting platforms to tighten their user verification processes. Think X's blue check mark for verified accounts. These practices are likely to become the norm, not the exception.

In this trend, trust becomes the currency of connection. That means credibility isn't an option, it's a necessity.

Personalized and Relevant Messaging

When it comes to your outreach messages, the bar for entry is a relevant and personalized message.

Each message must reflect the unique needs and interests of the individual it's targeted at.

This isn't just about avoiding spam filters; it's about making a real connection (people don’t connect with robots).

Another way to think about it is that you're not just sending messages — you're conveying a value proposition.

From the very first interaction, you need to make it clear what you offer and why it matters. This also lets you further qualified leads.

The Importance of Having a Process

With everything changing, I asked Doug what he believes will stay the same. Do we accept that the winds of change are now forever chaotic?

Where can we invest effort in sales and marketing that’s sure to yield positive results?

Regardless of the evolving volume and rhythm of outreach, the need for a well-structured strategy isn't going anywhere.

It's not so much about following the rules; it's about iterating frameworks that work. Processes are necessary to bring consistency, efficiency, optimization, and continuous improvements.

The Need for Tracking

One of the processes is tracking performance data.

Without tracking results, you can’t take data-driven steps toward achieving your goals.

However, performance tracking shouldn’t be treated like an administrative task. It requires experience and critical thinking to accurately assess your outreach efforts, spot emerging trends, and make decisions rooted in solid data.

By monitoring metrics such as outreach volume and response rates, you're unearthing invaluable insights that have the power to shape your tactics and overall strategy.

These statistics, when applied, work to build your roadmap to future success.

Split-Testing for Optimization

Once you have tracked performance and gathered insights, it's time to experiment and optimize. Split-testing (aka A/B testing) is a powerful tool that lets you determine what’s performing best within a unique context.

Continuous testing and refining are about staying agile in the face of ever-changing market dynamics.

You're not just adapting to keep up; you're evolving to stay ahead in volatile markets.

Evolving CTAs

Crafting the perfect CTA isn't about being assertive. It's about striking the right balance between persuasive authority and delivering valuable information.

What direction does your audience want to go in?

What CTA speaks to that choice?

Customizing CTAs to buyer stages maximizes engagement and drives conversions.

While the basics of a CTA are to get a 'yes' or 'no' to qualify prospects for the next stage of the funnel, the level of friction prospects experience when pushed to take an action remains in a state of flux.

Use split-testing and personalization to keep your CTAs fresh and effective.