How would you market legacy B2B software?

Let’s say you have an (older) product with high brand recognition, but UX and feature set might not be as relevant or modern as newer competitors in the space.

  • Where would you focus resources ($$)?
  • Would you invest more heavily in Product / Engineering improvements?
  • Do marketing playbooks stay the same regardless of product experience?

Hey @leah.howell welcome to the community.

Great question.

I believe Peep talks about this a lot on his how to win podast and its a common topic in a lot of Do you even resonate posts on his linkedin.

I have watched many of those and from what i can recall he is very strong on the idea that platforms do not win on features as most people end up building the same things and there is very little between most top competitors. So other things like positioning and brand story come more into play. So your brand recognition would come into play here.

As a product manager I would be very careful about pouring heavy resources into product / engineering improvements as the solution. That won’t get you new customers.

I would firstly watch and read up peeps linkedin posts and videos around messaging. Youll find a lot of stuff there that will help you with this question, its mostly around this topic.

Do marketing playbooks stay the same regardless of product experience?

Can you please help me understand this question a little more so I can better help you. This could vary a lot depending on context. Perhaps if you could give me a practical example or two?

Thank you for the response. I follow Peep and Wynter podcasts, but I assumed brand positioning and story would only go so far unless the products are at least pretty close to the same in terms of features and UX.
But what if they’re not? What if product A is actually less superior than B and offers less? Does it matter?
As a real-world example, my company does a good job of bringing in sign-ups but we have a hard time converting them to paid subscribers. So, internal conversations continually circle around “Are we bringing in the right people? OR Is our product not meeting their expectations so they don’t convert once they’re in.”


One more way for me to ask a similar question… Let’s say you have a Software Product and it’s competitive in the market, but then you just maintain – no new features or experiences, just fixing bugs and making it work. At what point (if any) would you shift from marketing brand story and positioning → product improvements to stay competitive? Does positioning have a shelf life if product improvements don’t come alongside?

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What did a recent user survey tell you about why people love / keep paying you?


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Hi @leah.howell

It sounds like the base is solid. Good brand recognition, and the customers that convert are happy. But converting new ones is the issue.

I discussed a very similar issue with Peep and Merritt recently. I dont think overall positioning would go away or you would switch from it. But it would be the strategic narrative that sets the tone for everything else.

If your delivery pipeline is a set of features rather than products/content/services. Then the messaging and positioning around the product marketing would work in tandem with your overall narrative.

Have you done any estimation work with your Product team around the gap between your product and the competitors? Getting a handle on the problem size may help frame a bit answer.

What does getting close mean in terms of effort?


Hi @hesh_fekry – you described the situation exactly. :+1:

Was that conversation in podcast or written form? :pray:

In terms of product gaps, they are quite large and limited engineering resources I don’t see us “catching up” in terms of features (assuming those competitors continue to advance as well).

Our roadmap for the next 3-6 months is focused on updating invoicing and billings systems to help us operate more efficiently and experiment with trial lengths and pricing plans. Not user-facing product changes or experiences.

All that to say, I’m curious about this relationship between marketing <> product and when (if) it makes sense to shift company $$ from marketing budget to product and engineering.

Not expecting any easy answers, but I appreciate the dialog.


Unfortunately neither. But a discussion around the same topic :slight_smile:

Curious to hear what Peep thinks. Ill see if I can grab him on the topic.

@merritt What are your thoughts here?

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I don’t know if anyone, in their right mind, would say that product doesn’t matter. But there are definitely situations where feature parity matters less. There are also strategies to win that revolve much more around sales, marketing, distribution channels, packaging and pricing. These are big questions.


Thanks @merritt for chiming in.

@leah.howell we have a few playbooks just about to drop around this topic. will share shortly.

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we have a few playbooks just about to drop around this topic. will share shortly.

@hesh_fekry did you find those playbooks for Leah?

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They are in final copy edit stage now. Should be very soon.

@leah.howell almost there :slight_smile:

Did you have any movement on the topic internally? I am curious.

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Thank you! Internally, I’m framing the conversation around improving our CAC and shifting that budget towards prod / dev resources while we experiment with some cheaper channels for growth. Otherwise with our current product gaps it feels like we’re throwing money out the window.

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experiment with some cheaper channels for growth.

Well on this front i believe we are all in the same boat. I think you will like what we will be putting out over the next couple of months at CXL. Our blog, course and case study content will be all about this topic specifically for the forseeable.

Anything in particular you would want to see to help you discover these channels?

I asked @naomi_kramer and @chad_wyatt to prioritize those differentiation playbooks. They are being converted from this course by the way. Do you have access to this?

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I don’t have access to that course, but I found this discussion related to this on LinkedIn and it’s gold. I like the discussion because it’s talking about when to focus on growth vs. product market fit and churn issues. Anyway, not sure how you’d make a playbook out of it, but wanted to post here in case anyone was following along.

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Thanks @leah.howell going to paste the embed here for a preview.

Churn is a PMF problem. Taking a step back on focussing on Product is key to survival

I found this one quite interesting.

Quite a few different approaches on there indeed. Did you find something that resonates with your situation the most?