The 'Undercover Buying Journey Walk’: A powerful exercise for CGOs, CMOs, and CROs in their GTM Strategy

In today's competitive B2B landscape, mastering your company’s buying journey is not just a strategy—it's a necessity. Drawing inspiration from the popular TV show ‘Undercover Boss,’ where executives disguise themselves to gain firsthand insights into their own companies, every CMO, CRO, and CGO should take a similar approach. By experiencing your company’s buying journey firsthand, but undercover, you can uncover pain points and identify small, missed nuances that break the desired experience, understand and feel customer sentiments, uncover their points of engagement friction, and give your continuous to-do list for CANI (Constant And Never-ending Improvement).

While you can always set up a transformative process for this exercise, here’s a quick and significant checklist that helps you walk the buying journey digitally to surface and improve your target audience’s buying experience quickly. But first…

Why Go Incognito?

Going undercover (or incognito in the digital world) allows you to see your company’s buying process through a customer's eyes. It helps you identify pain points, understand customer sentiments, and pinpoint areas for improvement.

Checklist to Walk the Buying Journey ‘Undercover’

#1. Research Keywords Incognito

Identify the keywords relevant to your industry, your products, and your competitors. What terms are potential customers using to find solutions in your niche? This will provide insights into how they might discover your website. Do this incognito and start leaving behind intent.

#2. Visit Your Website

From the same unclosed incognito window, visit and navigate your website and leave behind a cookie as if you are a potential buyer. Evaluate the landing page, ease of navigation, and overall user experience. Is the website intuitive? Is information easy to find?

#3. Fill Out a Form / Register for an Event

Complete any available forms, whether it’s to download a whitepaper, subscribe to a newsletter, or inquire about a demo. Do not give a phone number, but do leave behind a legit email ID that links back to a potential LinkedIn profile. Assess the simplicity, clarity, and the amount of information required.

#4. Request a Demo with Just an Email ID

Ask for a demo of your product or service. Observe how quickly and efficiently your team or systems respond. Is the process seamless? Would you feel valued as a customer? Does the content interest you further in continuing research or engagement?

#5. Review Digital Touchpoints

To sign this off, record your feelings, thoughts, and ideas. You can now come clean and ask for and scrutinize every touchpoint, from automated emails to live interactions, by asking your team to run some simulations. Does the communication delight you? Is it personalized and addresses your pain points? How effectively do the nurture emails listen and respond to your needs?

Please keep this in mind! This simple starter checklist will not uncover everything needed to seamlessly architect and orchestrate your target’s buying journey, but it will highlight the need for each of your demand-gen, campaign, and sales teams to have a customer-focused mindset.

Here’s a Ready Reckoner to Evaluate Your ‘Undercover Buying Experience Walk’ Against:

Evaluation Metrics:

• Delight and Surprise: Does the experience exceed expectations in a positive way?
• Relevance: Does the communication speak directly to customer problems?
• Personalization: Are emails personalized and indicative of genuine care in solving customer problems?
• Efficiency: How quick and effective is the response once interest is stated?
• Tone and Tenor: Is the tone of communication professional yet approachable?
• Event Logistics: How clear and efficient is the communication regarding events?
• Follow-Up: How promptly and effectively is follow-up communication handled? How many hands does the follow-up change

Some Final Tips for Structural Improvements:

Separate Makers from Checkers

This is basic but often needs to be added within organizations and their processes. Ensure that the creator of any communication (emails, web pages, content) is not the one who approves or publishes it. Implement a checking mechanism where a different individual reviews each piece—record who created and checked every piece of content.

Utilize Generative AI for Personalization

Create a consistent personalization voice using a Generative AI tool. Develop a ‘context prompt’ for every campaign, ensuring all communication aligns with it. This context prompt should inform your content and communications inventory, enhancing consistency and relevance. Equip your sellers with the same generative AI tool to keep their messaging and differentiators aligned with the brand and campaign context.

In Conclusion…

By walking the buying journey in incognito mode, you acquire an unfiltered view of the customer experience. This undercover exercise is invaluable for any CMO, CRO, or CGO aiming to optimize their company’s buying process. It’s not just about identifying problems but transforming these insights into actionable strategies that elevate the customer journey.

In B2B marketing, a seamless, personalized, and efficient buying experience often sets the industry leaders apart from the rest.

Feel free to walk the journey in disguise and share what you discover that surprises you!

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