Top challenges Technology Startup CMOs face - PART 2

Top challenges Technology Startup CMOs face - PART 2
B2B Inbound Marketing Strategy


If you are a Tech CMO you are probably having similar challenges so read on and see that you are not alone. In my previous post I shared with you 9 of the biggest challenges B2B Tech CMOs told me they face today.

In this article I reveal to you the next 9 and some further suggestions we had for them.

Let us know if you identify with any of these challenges and which hacks, if any, helped you through.

10. Inbar Yagur-  CMO @ TrenDemon

My biggest challenge is that I don't have time to properly reflect. I learn most when given the opportunity to identify and correct my mistakes. Everybody is so busy looking ahead they forget the power of looking back.


This is one of those challenges that is not talked about enough.  We see this all the time as we are always looking at what we are doing next.  At Penguin Strategies we frame each new activity or campaign in the form of an experiment where we start with a hypotheses which states what it is we are going to do what result we expect, how long will it take and how much will it cost.  This way we run the activity and clearly see if it was a success or failure. Both outcomes help us frame our next hypothesis and allow for continuous improvement


11. Chris Osika-  CMO @ Telestream

Quantifying the ROI of marketing spend and thus optimizing across the alternative options.


ROI can be elusive to many marketers as it comes down to expectations.  Marketing is not about creating pretty things anymore it's about getting the sales process started. Strong sales and marketing alignment means marketing knows exactly what they need to produce and can then go ahead and measure that.  This is easier said than done because in order to get those leads we need to reach our buyer persona online get them to engage and assess their readiness before declaring victory and handing it over to sales.  All this said, it is still very difficult to calculate specific ROI sometimes especially for B2B Tech and especially when it comes to B2B social media marketing. This is summed up really well by Gary Vee in his blog post - What’s the ROI of your Mother? 


12. Jake Sorofman- CMO @

The content bottleneck. The content supply chain is the rate limiter to digital marketing maturity. You need to feed the beast. Also, multichannel attribution.


Content guru, Neil Patel provided a great hack to this problem on a previous post in Quora. According to him his content creation process was completed in these two easy steps.

1. Find relevant blogs in your space to see what type of content have done well for them.

2. Take their best performing topics and add your spin to it. For example, if a top performing post on your competitor's blog was "CIOs, here are the 3 secrets to building a great customer experience." Then your spin could be, "CIOs, here are 25 top ways to build a great customer experience."

This process works because more than likely you are targeting the same audience as your competitors, so no need to bang your head trying to come up with different topics.

On multi-channel attribution, it is a trial and error process where you may start with 2 or 3 channels and over time it becomes clear which channel is more beneficial to your business in terms of lead generation, customer acquisition, and engagement with your followers. Always pay more attention to the channel most beneficial to your business in those terms, not which channel is trending.


13. Eric Quanstrom-  CMO @ CIENCE 

The biggest challenge for me is resources. We've deliberately over-indexed our organization towards our internal sales development team-- which makes sense as this is the business CIENCE is in. As such, most of our Inbound initiatives have been under-staffed, even under-funded to date. This is changing-- but not as quickly as I'd like...


This is the struggle of a CMO not being giving the resources to execute on their strategy. Inbound marketing as a strategy is often doubted by B2B Tech companies as they do believe that internal sales methods are more effective. However, statistics have shown that some level of inbound marketing is needed to better qualify the leads and move them further down the funnel.

That being said one solution would be to establish alignment with the marketing and sales team. How do you accomplish this?  By proving to be beneficial to the department by bringing qualified leads to the sales team so the board willingly funds these inbound marketing activities. With the help of portals such as Hubspot, for example, the sales enablement software would prove very beneficial to the sales team as well as the inbound marketing team as it would provide insights on qualified leads.

This way the sales team can concentrate on selling to the ready buyer as the marketing continues to nurture the ones that are not yet quite ready to purchase and the beauty is, it all works towards the same goal of generating more revenue for the company.

14. Ron Gant
- Director of Marketing @ Info Tech 

I do not work in a commodity marketing world. Technology marketing to engineers and constructors is very different and largely relationship building. The age-old marketing statistics of reaching x% that converts to y% leads and yields z% revenue where x is in direct relationship to y & z does not apply. Increasing X does not necessarily increase z, as x has a finite and smaller number. Can you tell I am an engineer converted to marketer, LOL. So, our biggest challenge is to identify within the constraints of today’s marketing, who those special, influential contacts are, establishing a relationship and then nurturing it with information they find interesting, valuable and worth pursuing further. You must do that through virtual and personalized touch, that gives them a yearning for more information from you. In the end, you want them to seek you as much as you seek them. The relationship becomes mutually beneficial and business relationships become personal relationships and possibly even friendships over time. Probably wordier than you desired, but now you know how an engineer becomes a senior marketer. Also, some of my best friends were once just leads.


Influential contacts can scale your business to new heights when they promote your company to their loyal community of followers. They are more trusted than ads and do not disrupt their users experience. Therefore, they are more authentic.

When it comes to establishing a relationship with an influential contact, we suggest doing a bit of research to find out what they are passionate about, provide high-quality products/services that they can identify with and be proud to be associated with. When there is alignment between their goals and the company’s, they will seek you out and happily promote you to their networks.


15. Fred Studer-  CMO @ FinancialForce

It’s the balance between the science of Demand generation, the art of branding and communications and the reality of authentic customer/product value.


These are all part of the same puzzle aren’t they? Done right, the ultimate goals of the business will be achieved. The way I suggest to approach this is by starting with a compelling overarching strategy which includes what have we created, for who and why should they care? This will lead to defining what success looks like and how we can measure it. Once we answer these questions and come up with the right story, we can start telling it and how these products/services provide value.  This will then lead to the right tactics to get the message out and generate the results towards the success criteria defined.


16. Jonathan Moran- Global Director of Marketing @ Earnix

It’s challenging today to find and retain rockstar marketers – in order to create continuity inside of organizations. Marketers today must be able to: 
• Think, message, and position strategically 
• Dig in to data using analytic techniques – to position and present results 
• Take technical capabilities and translate them into creative communications 
• Possess an eye for design and visual and interactive appeal 
• Have a working knowledge of their industries and technologies 
• And communicate and collaborate well – across time zones, cultures, and geographies – with agencies, analysts, partners, and even academia. 
If you’re a senior marketer and are working with great talent – I think it’s imperative to reward in order to retain.


Marketers, like their CMOs, are lucky enough to be able to exercise both parts of their brains. The creative side and the analytical side. Finding these individuals and retaining them, however, is not always easy.

One possible solution to this challenge is to keep your employees as happy as your customers. Because the reality is they are your first ambassadors.

Run surveys and polls to make sure the working environment is conducive to productivity, and most importantly, listen to their input. They interact with the customers and their insights are invaluable to your progress as a company both internally and externally.


17. Seth Redmore- CMO @ Lexalytics

Simplifying a highly technical product into bite-sized benefits.


Most B2B Tech companies I talk to tell me the same thing.  I am sure you have a team of great marketers but you won’t be able to write about us because our tech is complicated and unique.  I think the key that makes us more successful in marketing tech companies then others is our approach. We believe that the best tech marketers were techies first then fell into marketing later. I include myself in this as I started my career as a software developer and moved slowly over to marketing over the many years I have been in tech.

One tactic that has worked for us to simplify a highly technical product into bite-sized benefits is ensuring that our writers have an in depth understanding of the product in order to communicate the VALUE to the target audience and not just the benefits. Time and time again we've seen that even though you think you are targeting the CIO because your product is highly technical, often times the decision makers are CEOs or CFOs both of whom may not have the background to understand the technical aspects of your product but can surely relate to the value it brings to helping them achieve their business goals. 


18. Yam RegevMy biggest pain is automation. I’m trying to avoid it as much as possible and place users first and front. 

However, it’s a tough task as I’m still not sure about the right ratio between for tech in my marketing organization and the exact and right procedures of human involvement.


One of my favorite books written by Ben Horowitz of Andreessen Horowitz is The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers.  This is a must read book for every executive in a startup.  One of the many incredible pieces of advice he gives is “Give ground grudgingly” he says this in relation to a growing company that starts to need more structure for communication.  He relates this to Football where the offensive lineman’s job is to protect the quarterback from rushing defensive linemen.  The same can be said for automation. Personalizing every email and interaction will definitely be most effective but that will prevent scaling so finding the write mix through segmentation, account based marketing and technology is the only way forward.

To help get you started, we've put together this guide to B2B marketing automation.

Now, ladies and gentlemen, I believe with this cheat sheet, you can look those CMO challenges in the eye and take them head-on. Because you are prepared for at least 18 of them.

To me, that is a hell of a head start!

Perry Nalevka

by Perry Nalevka on June 13, 2018

CEO of Penguin Strategies