Why Founders Struggle with AI in Sales & Marketing (and How to Get it Right)

Welcome to the 24th Edition of Future is Bright – your go-to newsletter exploring the transformative power of technology, AI, and innovation in today’s fast-evolving landscape. In this edition, we dive into why many founders are misstepping with their AI strategies, especially in Sales and Marketing. With insights from real experiences helping startups navigate AI’s complexities, this issue sheds light on how businesses can avoid common pitfalls and drive real value through a strategic AI approach.

Why Founders Struggle with AI in Sales & Marketing (and How to Get it Right)

In my experience, a gap between vision and reality regarding founders and AI often exists. Especially in Sales and Marketing, there’s a sense of urgency to adopt the latest tools, automate processes, and keep up with competitors’ tech stacks. However, as I’ve learned while helping several startups over the past 18 months, from Fintech to Cybersecurity, the tech itself is never the problem—the challenge lies in creating a meaningful strategy that AI can amplify, not replace.

Fintech Company Trying to Find Its Feet in Sales & Marketing:

Over a year ago, I started working with a Fintech company in the payments space. They had a high-potential product but needed help to hit their sales targets. Their team had invested heavily in an AI-driven marketing stack, expecting it to fast-track conversions and lead generation. Their setup was impressive on paper: predictive analytics, real-time data insights, automated email flows, and an AI-powered lead-scoring model.

But despite all this, the leads weren’t converting. Marketing campaigns felt generic, and the sales team was overwhelmed with “qualified” leads that weren’t close to buying.

Misalignment Between Tech and Sales Strategy

Their challenge was one I’ve seen repeatedly: relying on tech without a clear roadmap. Like many others, this company had made the common mistake of letting technology lead its process. Rather than enhancing a solid sales and marketing strategy, the AI tools dictated what it should do, creating more noise than clarity.

The AI tools needed direction and a clear understanding of their ideal customer journey. They churned out data and reports with no actionable insights aligned with the company’s sales goals.

Grounding AI in a Customer-Centric Strategy

As a Fractional CRO, my goal wasn’t to throw out their existing tech stack but to redefine the strategy behind it. We focused on identifying the high-value touchpoints in their customer journey and revisited their buyer personas precisely. This wasn’t about segmenting broadly; we used AI insights to drill down into granular details, finding where each persona’s interests aligned with our messaging.

For example:

• Lead Scoring Overhaul: We restructured their lead scoring criteria based on genuine buying intent rather than just engagement data.
• Personalization, Not Automation: We leveraged AI to personalize touchpoints instead of fully automating outreach. Campaigns now included tailored messages and offers that reflected each prospect's stage of the buying journey.

Within six months, the change was noticeable. Their conversion rate increased by 30%, and the quality of leads improved substantially. The sales team finally focused on prospects with real potential, not just high scores.

Something to learn from my other Clients

Here are some valuable takeaways from this and other cases I’ve handled over the past 18 months with Fintech, Cybersecurity, and AI companies.

1. AI Works Best with a Clear Sales Roadmap: In helping a Cybersecurity startup, we realized the importance of mapping AI capabilities to a real, stage-by-stage sales process. Rather than expecting AI to identify and “create” leads, it should empower your team with real-time insights, helping each sales rep understand exactly where a lead stands and how to approach them next.
2. The Role of AI is to Enhance, Not Replace Human Judgment: Working with an AI startup, I saw firsthand how founders often want the technology to do everything—from lead scoring to closing. But the most effective AI tech stack we created left room for human decision-making. We focused on predictive insights to help their team engage with clients when the timing was right and with the right message.
3. Effective AI Needs High-Quality Data: With the payments Fintech, we spent considerable time cleaning and restructuring their data. Founders often overlook this, but AI is only as strong as the data it’s fed. Working on data health can be the difference between actionable insights and empty noise.
4. Focus on Personalization, Not Just Automation: Automated workflows are great, but generic messages rarely resonate. AI’s strength is in helping you understand your customers at a personal level. With the Cybersecurity company, we started using AI to assess behavioral data, which let us reach out with content that directly addressed each client’s unique concerns.
5. Measure Success Beyond the Initial Metrics: Founders sometimes need to be more focused on metrics like lead volume, missing out on the quality of engagements. AI-driven strategies should be measured not just by volume but by customer lifetime value, customer satisfaction, and meaningful engagement.

A Note for Founders

If you’re a founder, it’s essential to remember that AI isn’t a magic button. It requires a thoughtful strategy to make it truly effective. Instead of viewing AI as the driver of your sales and marketing engine, think of it as a co-pilot—something that helps you steer with accuracy but never takes the wheel completely.

If this resonates with your challenges, join me and fellow Fractional CXOs Rajiv Viswanathan & Archita Fritz on October 16 at 6 PM for a LinkedIn Live Webinar on AI in Sales & Marketing. We’ll dive deep into practical, real-world strategies, discuss pitfalls to avoid, and explore how to build a tech stack that genuinely works for you.

Streaming live on LinkedIn , with simulcast on Meta , X , and YouTube Let’s talk about making AI work for your business!

AI is transforming the business landscape, but only when integrated with a customer-focused strategy.?Future is Bright?is here to support you in navigating these revolutionary changes and maintaining a competitive edge. Be sure to keep an eye out for our upcoming publications, where we will delve deeper into the convergence of technology, innovation, and leadership.

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