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H2H sales podcast 2

How to Get your Sales Content Right 

Bart Kowalczyk, MD of AutomateNow and Leslie Douglas, VP of Membership and GTM Strategy at Sell Better by JB Sales.

AutomateNow Podcast Leslie Douglas


Leslie Douglas got into Sales by accident. Her ambition was to become an international conference planner and organizer. But, she was informally head-hunted at an international hospitality conference when a woman she was chatting to invited her to come and interview for a sales role the next day at her company.

She ended up acing the interview and was entered into the company’s sales training program before she was given her own patch, selling to the hospitality industry.

Her first few weeks did not go well. She would arrive at a hotel and ask for her contact at the front desk, only to be told that she had to make an appointment. Of course, that was not as simple as it looked, because getting past the PA or other gatekeeper on the phone to make that appointment was never easy. Leslie’s mentor at the company explained how to enter hotels by the back door, and find her prospect’s office to speak directly to them. At first, she would be stopped and questioned by hotel staff, ending up back at the Reception desk. But, she learned how to act as if she belonged, greeting people as if they should know who she was. She learned the importance of confidence in Sales.

Importantly, this background in F2F sales the old-fashioned way, researching her prospect and making a cold pitch, proved to be the perfect apprenticeship for today’s human-to-human sales approach.

Marketing – An often-untapped source of great content

The starting point for sales today is content. Whether that is the words you use on the phone to a prospect or the emails you send – good content is crucial.

Leslie told AutomateNow:

At JB Sales we have a great marketing department who create very good content for our website. They’ve taken time and care over it, so it communicates and flows well. That’s often my starting point for crafting sales content. I’m sure it is a similar situation at most companies – you will find great content on your company website – Marketing have done a lot of the hard work for you.


How to research personalized content 

The only caveat is that Marketing produces communications that is aimed at the whole of the target market – it’s one-to-many content. In Sales, we need to be thinking always one-to-one. We need be personalizing our content for each prospect.  

There are two main routes to personalizing your sales communications so they are relevant to your prospect.

One way is to research your prospect thoroughly. Search through existing information on your CRM, see if there is any information about them in the press or online. You might want to ask them about a recent holiday, congratulate them on an anniversary of their business or the birth of a child.

Also, check the company website and search online for news about planned or latest developments. Seek to answer the question in advance: Why is it a good time for me to talk to you now? So, you might tell them that you saw on their website/read in the newspaper that they are expanding their markets to Poland: this is a perfect opportunity for some synergy between us.

Look at the prospect’s company values and philosophy – is there some overlap there with you that is worth mentioning? 

Ask this one question

Once you make the call, it is likely that you won’t make the sale straight away. Before you hang up, ask one question to keep that door open. 

Leslie sells to Sales VPs, so her question is:  

I am constantly coming across great information about sales teams. The most common topics are time management, new tools and techniques for your sales teams and frontline leadership. Are any of those interesting to you? If I come across anything on those themes, would you like me to send it your way?


The prospect always picks a theme – it’s that powerful rule of 3 – a limited list of options. If you just ask what a prospect is interested in, they might answer “Anything, really,” or just remain non-committal. But by guiding them to choose a topic from a list, you have found a source of personalization just for them. You can send them an article every 4 or 5 weeks, with no ask, no CTA, just relevant, personalized information with no expectation of reward. Mention specifically a section or a sentence that you think is relevant to them. Or explain why you the article made you think of them. When it does come time to reconnect, you have provided value and built a relationship foundation to go forward.

Refine Content based on job title 

The other method is to base communications on job title. Leslie usually sells to VP level – VP for Sales, etc. 

If there is a job advert for VP level, you can find info about what the company is doing and how the role will be held accountable – what are their duties, what is the company philosophy and what are their values? 

Some of the pitch you use will then be specific to the company, but some will be generic - reusable for other prospects at the same level in other companies.

Build desire over time. Talk about them, not you.

Nowadays, people can research you and your company in their own time, when and if they are interested. Google, LinkedIn and other online sources will provide all the information they need. Therefore, there is no need to bombard your prospect with facts and figures about your company and why it is so great. 

Dedicate your time instead to researching the prospect, providing relevant personalized information, and building a relationship over time. Your prospect will find out about you without your help. And will value the communications they have from you.

Omni-Channel Marketing – show up consistently

This leads us neatly in a loop back to Content. If your prospects are going to research you, better make sure there’s a lot of good information for them to find!

Your throwaway comments on social media just became important. Your contributions on LinkedIn, even when just reacting to someone else’s post, help define you, your company and your brand. 

You’re not sending information to your prospects – you’re leaving it lying around for them to find in their own time. Make sure they find good stuff. 

If you find it daunting to create your own content, comment on posts by others on LinkedIn and build your presence on the platform.

Post little and often – show up consistently and have your own voice.

If you’ve enjoyed reading this short article and would like to learn more, subscribe to AutomateNow H2H Sales and Marketing podcast channel and we’ll keep you informed!

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I specialize in optimizing the buyer's journey, providing top-notch sales enablement training, spearheading new business development, orchestrating engaging events, and sharing insights through podcasts. My mission is to drive growth, enhance customer experiences, and empower sales teams to excel. Let's elevate your business together.