The Good, Bad, and Ugly of AI in Revenue

Hey ,

The last few weeks have been a whirlwind. Lots of travel, tons of conversations, and a sense of pride I haven’t felt in a hot minute. We’ve seen the GTM Gap™ gain more and more recognition from founders, revenue leaders, and investors alike. It’s been humbling to see it make its way into two more board decks and continue hearing praise for how it’s helping companies bridge the gap between strategy and execution.

One of the things I’ve come to appreciate about my role as a fractional leader is the opportunity it gives me to form deeper, more personal relationships with my clients. This level of involvement allows me to truly understand their challenges and work alongside them to build something lasting.

Just last weekend, I was reminded of how special this can be. One amazing client (who prefers to remain anonymous) surprised me and Zachary with tickets to the Warriors vs. Pistons game in SF. Zachary has always dreamed of seeing his favorite team play at home, and this thoughtful gesture made that dream come true. We had incredible seats, the game was neck and neck until the very last play, and it was a fantastic way to spend some father-son time. No screens, no AI, just us enjoying the moment and the game.

Which brings me to the topic of this newsletter. As much as AI continues to improve and bring amazing capabilities, it can also have its darker side. AI has the potential to be both a force for good and a source of frustration and challenge, especially in the world of revenue. So, in the spirit of that weekend without screens, let’s dive into the Good, Bad, and Ugly of AI in Revenue.

Estimated reading time is 3.5 minutes. Let’s get to it.

On Deck:

• The Good, Bad, and Ugly of AI in Revenue.

• Marketing Tip of the Week, The Pressure is Real - Powered by Decoded Strategies

• Episode #83 The Brutal Truth About Startups

The Good, Bad, and Ugly of AI in Revenue

AI has exploded into the revenue world, bringing with it both incredible advancements and some truly cringe-worthy missteps. When done right, AI can be a powerful force multiplier, helping teams move faster, smarter, and more efficiently. But when misused? It becomes yet another source of noise. Spamming inboxes, creating surface-level engagement, and making sales teams look robotic rather than human.

Let’s break it down:

The Good: AI as a Force Multiplier

When AI is used correctly, it unlocks potential that simply wasn’t possible before. It allows revenue teams to work smarter, focus on high-value activities, and automate the tedious, time-consuming parts of their jobs. Here are a few ways AI is accelerating revenue:

1. List Building, Enrichment & Prospecting at Scale: Tools like Clay and Freckle have taken list-building and data enrichment from a manual grind to a highly automated, highly targeted science. AI can pull relevant data, segment audiences, and enrich contact lists in ways that previously took hours (if not days) to do manually. In 2025, you should not have your team spending time manually building and enriching lists.

2. Revenue Models in Minutes, Not Hours: Finance teams and RevOps leaders no longer need to spend hours in spreadsheets. AI-powered platforms like Pigment and Abacum can build dynamic revenue models in real time, factoring in variables like churn, sales velocity, and conversion rates with a few clicks. This allows leadership teams to make data-driven decisions faster and with greater accuracy.

3. AI-Powered Coaching & Call Analysis: Tools like Attention have made sales coaching scalable. AI can analyze call transcripts, identify key patterns, and offer reps real-time feedback on objection handling, talk-to-listen ratios, and deal risks, eliminating the guesswork from sales performance improvement. Couple that with one-touch emails, real-time CRM updates, and powerful AI agents that can do just about any task and you’ll see why we recommend Attention to all of our clients.

4. Predictive Forecasting & Deal Intelligence: Platforms like Clari and Hubspot’s Breeze help revenue leaders see around corners, using AI to identify at-risk deals, flag pipeline inconsistencies, and predict revenue outcomes with greater accuracy than traditional forecasting methods.

These AI-driven tools aren’t just about saving time, they’re about making revenue teams more precise, strategic, and focused on the right opportunities. But while AI has its advantages, there’s a dark side that can easily derail revenue teams if they’re not careful

The Bad: When AI Makes Revenue Worse

For every great AI-powered revenue tool, there’s an equally bad one being misused in ways that create friction instead of value. AI is meant to enhance human-led sales efforts, not replace them. Here’s where things start to go south:

1. The AI SDR Epidemic: AI-generated cold outreach is at an all-time high, and the problem is… it’s terrible. The moment a prospect realizes they’re engaging with a bot, trust is lost. AI SDRs and the companies behind them have yet to truly figure out how to harness the power of AI to get this right.

2. Crappy Automated Emails: You’ve seen them. Hell, I get 10+ a day. The poorly written, clearly auto-generated messages that start with “Hope you’re doing well” or “Quick question for you…” AI can help personalize at scale, but when misused, it creates mass messaging that lacks the one thing prospects want: a genuine, human connection.

3. AI as a Short-Term Hack, Not a Strategy: Companies chasing AI as a shiny object often throw automation at problems that require strategy. AI can assist with prospecting, outreach, and engagement, but if the underlying messaging and ICP targeting are wrong, automation just amplifies bad habits.

4.  Over-Reliance on AI for Deal Closing: AI can help with insights, but closing a deal still requires human-to-human interaction. AI-generated follow-ups and deal nudges often feel impersonal, generic, and out of touch with the real concerns of the buyer.

Too many companies are treating AI like a “set it and forget it” solution. The result? More noise, more bad experiences, and a growing skepticism of AI-driven sales efforts. But while the “bad” is mostly just ineffective, there’s an even uglier side to AI in revenue… one that can actually hurt businesses.

The Ugly: When AI Backfires in Revenue

AI isn’t just misused, it can be downright dangerous when implemented without oversight. The ugliest AI use cases are the ones that destroy trust, damage reputations, and leave companies scrambling to recover.

1. AI-Generated Lies & Hallucinations: AI doesn’t “know” things; it predicts patterns. This leads to AI tools generating completely false information in sales emails, prospecting efforts, and customer interactions. There have been cases where AI-assisted reps sent prospects wildly inaccurate stats or made up case studies… instantly damaging credibility.

2. Deepfake Sales Reps & Synthetic Voices: Some companies are experimenting with AI-generated sales reps and voice bots to handle prospecting calls. While impressive in concept, the reality is unsettling. Buyers don’t trust AI pretending to be human. The second they realize they’re talking to an AI-generated persona, it’s game over.

3. Mass-Scale Data Privacy Violations: AI thrives on data, but poorly managed AI tools can create compliance nightmares. Companies scraping and using AI to generate prospect lists without adhering to GDPR or CCPA regulations could find themselves in legal hot water. Hell, Apollo and Seamless just got the LinkedIn boot.

4. AI-Generated Contracts & Legal Risks: AI can assist in drafting contracts, but legal teams are already flagging issues where AI misinterprets terms, creates enforceability risks, and introduces errors that could cost companies millions. AI should assist legal teams—not replace them.

The ugliest AI failures don’t just annoy prospects—they create massive trust and reputational damage. AI is an incredible tool, but like any tool, it needs the right operators.

The Bottom Line: AI is an Add-On, Not a Replacement

AI is one of the most powerful tools in the revenue world… but only when used correctly. It can accelerate workflows, refine targeting, and improve efficiency, but it can’t replace human judgment, creativity, and relationship-building.

But the key is using AI to enhance human efforts, not replace them. Companies that treat AI as a shortcut will struggle, while those that integrate it intelligently will thrive.

AI is here to stay. The question isn’t whether to use it, but how to use it wisely.

Thanks ZoomInfo for Keeping This Newsletter Free!

ZoomInfo is the Go-To-Market intelligence platform that empowers businesses to grow faster with AI-ready insights, trusted data, and advanced automation. Our solutions provide a complete view of your customers, making every seller your best seller.

Marketing Tip of the Week, The Pressure is Real - Powered by Decoded Strategies

Marketers are constantly under pressure to deliver results RIGHT NOW.

But most meaningful marketing efforts take time to build

If you put pressure on your marketing team to react to immediate needs, you'll be stuck throwing a bunch of darts at a dart board, desperately trying to get one to stick.

Unintentional marketing won't work. Instead, start building for the long game. Focus on essential components of your marketing strategy:

1. Clarify your Ideal Customer Persona (ICP)

2. Develop clear messaging and positioning for your product

3. Identify the best type of content to amplify your brand story

4. Determine your most advantageous content distribution channels

5. Nail down the most important KPIs (leading and trailing indicators) to measure success 

Marketing takes time. 

It takes testing.

It takes failing a few times before you get it right.

So don't force your marketing team to produce immediate results. 

Instead, allow the time and energy to focus on getting the basics right, then iterate and repeat to build an evergreen marketing engine that can stand the test of time.

Episode #87 He Speaks to AI More Than Humans

In this week's episode of Bridge the Gap™, we sat down with Jordan Craqford, Founder & CEO Blueprint GTM, to really understand AI messaging, how to use it, and what to avoid.

Let’s face it, your outbound strategy is broken… and you don’t even know it. Jordan talks about all things outbound sales, AI-driven prospecting, and GTM strategy.

🔍 What you’ll learn:

✅ The biggest mistakes companies make in outbound sales

✅ How to craft messages people would pay to receive

✅ Why most Ideal Customer Profiles (ICPs) are outdated and ineffective

✅ The secret to finding, not filtering, your best-fit accounts

✅ How AI is changing the game for prospecting and engagement

💡 “Nothing changes if nothing changes.” If you’re still running the same playbook, you’re falling behind. Tune in to discover how to optimize your outbound strategy and make your GTM motion actually work in today’s market to Bridge the Gap.

Follow Jordan.

Shoutout to Pursuit for Keeping This Newsletter Free!

Finding A-Players who actually drive revenue in an ever-changing market is tough. Our partners at Pursuit hire for hundreds of companies and know what it takes to engage passive talent. If you need to hire top sales or marketing talent, we encourage you to reach out to our friend Jake at Pursuit.

Agree? Disagree? Have Questions?

We love engaging with our community—reply to this email with your thoughts, and let’s chat!

Talk soon,

Adam, Dale, & Jake
Helping companies bridge the GTM Gap™.