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Technical Leaders, Burning Cash And Building Your Success Team

This post is for CEOs and the technical leaders who help CEOs hit key numbers, generate sales and deliver profitably. We’re going to talk about technology, but this post is also about money – because cash flow is everything in business.

technical leaders building a successful team
Is your tech budget giving you a run for your money? This week's featured image was created using a prompt-based artificial intelligence artwork creation tool. You can see more pieces from the set titled "Tech Dragons" at the conclusion of this article.

Your technology represents a key interface point with your brand, from first impression to the coveted re-order. 

At it’s core your tech should essentially deliver the following dynamics measurably: 

  • Boosted Average Order Value – Because your content is educational and automated, your prospects will arrive to your sales page, or call with an expert informed and ready to ask meaningful questions about your best solution, not just your cheapest.


  • Boosted Lifetime Customer Value – Because your content is created to inform, engage and motivate people toward their best outcomes, your customer will trust your guidance and stick with you longer and come back more often.


  • Minimized Administrative Costs And Return Rates – Because your lead management and followup system is automated and your customers have already engaged in your content before they purchase, they are much less likely to need or ask for a refund.  This means less time spent with customer service and decreased dependency on a sales team because your content does most of that work for you. 

Is Your Tech Plan Clear or Murky?

In all areas of our lives, murky definitions are the root cause of suffering and poor results.

As CEOs and the technical leaders we hire, how can we expect our teams and contractors to follow through accurately if we don’t take responsibility for clear planning and specifics?

It’s tempting to think there’s a magical agency or consultant that will solve your tech problems, but as a marketing and technology consultant, I can tell you this is rarely true.

“Your ability to attract and retain qualified talent will largely determine the success and realized potential of your startup or new growth initiative.”

After leading tech and marketing strategies for almost twenty years, in my experience, CEOs who lean too much on outside agencies and contractors (to define & execute their tech) often sit with a heavy tech invoice and little results or revenue to show for it. 

Your digital assets (when built correctly) are high-leverage, highly sellable assets that look great on your balance sheet. 

Sadly, most leaders today don’t know the difference between a tech liability and a tech asset.

Here is what you need to know in order to change that.

Partner Carefully and Specify Clearly

Building a successful team starts with you and your technical leader.

Every piece of technology or software you choose is a marriage and a partnership.  When their servers crash or get hacked, so do your vital business functions. The same goes for the people you hire to lead your tech. 

Are you building a success team? Or is your team delaying your success?

Unfortunately, most well-meaning entrepreneurs fall short when it comes to knowing what tech to use and when. Use this matrix to get clear

Your technology has three levels that all need to be mapped carefully.

Your Core Business Communications (Cloud I.T.)

When it comes to your core business communications, think of items like your business cloud, email, docs, and your customer relationship manager (CRM).

Your Marketing Technology

Your marketing technology is typically your lead generation system, message automation, digital content, your website, landing pages, and your traffic partners.

Your Unique Delivery Stack

Your unique delivery stack is the combination of specialized technology that you need to deliver your unique product or service. We can’t add much to this conversation until we understand your business a little further.

In conclusion, avoid the alluring trap that one person can help you competently address all three of these areas. Instead, learn how to budget and break up these crucial roles and tasks in your business.

Fail to Plan, Plan to Fail

tecnical leader

Kyle Dammann is a passionate educator and strategic growth consultant.

If you skip clear and specific planning around these three areas of your business, you will struggle and most likely fail to meet your revenue goals. 

Teams who fail typically blame the agency, consultant, or department head.  

They also say things like, “traffic costs too much” (it doesn’t), or “the traffic isn’t converting into profitable customers fast enough” (leaky funnel, or too steep of a conversion ramp.)

After spending almost twenty years in marketing tech, I can personally attest that it’s critical as a CEO to have clarity and specificity with your unique tech plan.

Let’s itemize and review these sections more clearly.

  • Business Communications

This seems simple, but the devil is in the details. Email deliverability is a cat-and-mouse game, especially if you have a high volume of marketing and sales outreach happening.

Your technical leader should know specifically the latest standards for CAN-SPAM, CASL, and GDPR. Not only that, they should send you a weekly or monthly health check of your deliverability metrics.

Finally, your email, communications, and cloud docs should be properly archived and backed up for legal and contractual reasons. Applying these same criteria to your cloud document needs, including a security and password protocol for your team is a good place to start in regard to formulating your plan.

  • Your Marketing Technology

This area is where I have the most results and experience. Here is what you need to know in one paragraph.

While sales automation and marketing tools have gotten exponentially cheaper and easier to use, the knowledge of how to bring these systems together in one fluid profitable build phase and campaign is rare and highly valued.

That means the good ones are usually expensive and have long waiting lists.

But do not fear. Have heart. We want to help you slay your tech dragons without the marketing agency markup or long waiting list.


Q: Does traffic cost too much today?

A: Almost certainly not.


Paid ads remain the lowest cost and most reliable way to access your ideal buying audience than anything modern economics has ever seen. Ads don’t cost too much, but they can if your content and funnel aren’t converting efficiently.

A river of traffic is available, and a good campaign can transport your business to untold heights and opportunities. But if you get your marketing tech wrong you will struggle with inconsistent cash flow and all the stress that comes with it.

The rewards for getting your marketing tech right are as follows:

  • Lower cost per lead
  • Lower cost per new customer
  • Increased average order value
  • Decreased return rates
  • Lower customer service costs
  • Decreased dependency on fickle and expensive sales staff
  • Decreased dependency on agencies and their unnecessary markup

If you build your automations and content strategy correctly – your leads, prospects, and customers will self-qualify and sign up for your best product or service more frequently. It will also filter out the time wasters.

People have more choices than ever today. Your content should build a clear and obvious bridge for those who are ready to buy and (at the same time) help people become informed consumers so that when they are ready, they will choose you and your best package.

Sadly most CEOs pay $10-20-$100K+ for their website and leave the content writing to the front desk receptionist or the web designer at the agency who has never sold anything in their life.

You wouldn’t believe how many CEOs come to me after spending a truckload on digital with months gone by and no results to show.

If your Cloud I.T. is in good working order,  your marketing tech is where I recommend you spend next because it can move the needle relatively quickly, which will help to fund the rest of your tech needs below.

  • Your Unique Delivery Stack

This one is highly customized to what you do and how you do it and we have members in our network that can help you here.

The number one priority with your tech is good data, easy visibility, and consistent reporting.

As Jeff Bezos said, “data is the new oil,” and he’s right with one specific caveat:

Meaningful data is a primary business asset that you can use to develop near-psychic abilities for knowing what to do and when efficiently with minimal guesswork.

In business and in life success is primarily up to you.

What Does Your Success Team Look Like?

Growth is steady when you are calm and ready.

At Inner Circle, we pool resources, talent, and proven processes to help our members get clear, get funded, and grow.

If your marketing feels like gambling or guesswork, don’t do it.

Knowing who to surround yourself with is half the battle.

...Powerful Executive Success Teams Look Something Like This...

  • Chief Executive Officer | CEO:  The chief of promises made and promises kept.
  • Chief Operations Officer | COO: This No. 2 ensures the CEO can make good on said promises and doesn’t get sued or fired. They are also typically responsible for leading the charge on processing and documenting your key and supporting roles. When the marketing is hot, and the sales are coming in fast, your next bottleneck is always your ability to attract talent, train, and scale a successful team while preserving company culture and high-quality standards.
  • Chief Marketing Officer | CMO: This is rarely a full-time role in companies under 25 people, but generating a consistent stream of leads and prospects is critical to achieving growth and securing funding. More on this in a minute.
  • Chief Technology Officer | CTO: For non-software companies under five people, this is rarely a full-time role either. However, you need the right technical leaders and talent bought into your mission and on call to help specify and execute your tech needs, qualify software partners, and develop workflows.
  • Chief Financial Officer | CFO:  This is about ensuring your company has adequate funding and the money is in the right places at the right time to do the best good. Again, with companies under a certain size, the CEO usually manages the capital.

This ROLEs chart will help you to refocus and clarify what you need in your current level of growth.

Just don’t become a “crapitalist” along the way.

What’s the Difference Between a Capitalist and a “Crapitalist?”

If you are a CEO, or you work for a CEO who tries to do all of this themselves, works around the clock trying to make ends meet, and struggles to make good on promises, I invite you to get out of this crappy cycle yesterday.  

This is the story of the 90% of businesses and business owners who go about growing their business the hard way and their health, family, and personal credit are often casualties of this vicious crapitalist hero-victim cycle.

You are not a hero for grinding and starting a business in scarcity, and you are entitled to nothing except a fair shot at your slice of the market you serve.  

If you need funding, let’s talk about funding. If you need technical leaders, let’s talk about that too.

Working around the clock and sacrificing your health, relationships, and good standing is an outdated philosophy with toxic results and mountains of evidence to the contrary.  

Support is available if you are open to the idea.

Harvard Business Review has 25 years of good data that says teams who chronically overwork are less profitable, take more sick time, and have higher turnover rates, so…. STOP IT

Someone else says, “but we’re a small company, we can’t afford to hire an executive team.”

With all due kindness and respect, you’ve just disqualified yourself from building a category-leading brand and business and put yourself back in the camp of the 90% who will go out of business in the next three years.

Are you willing to learn new strategies? Are you willing to consider seeking help in the areas you aren’t strong? 

Your technical leaders ability to create a profitable process AND attract a talented success team (to deliver said process), is absolutely vital to your progress, profitability and satisfaction as a leader.

This is not rocket science, but it is a science, and most of the problems you face in your business have already been solved.

The clock is ticking and the decisions you make now will largely determine the profitability of the next 12 months. 

If you’ve made it this far, you are probably more ready for a profitable growth phase than you give yourself credit for.  Half the battle is unlearning the crapitalist, outdated, and misguided “grind culture” tactics that make for good headlines, but terrible leaders.

The other half of the battle is learning how to attract a powerful executive team who will help you launch and land your vision into its rightful place in the market.

At Inner Circle, we want to help you frame, fund, and fulfill the next level of your business profitably and with less stress, risk, and debt than you might realize is possible.

Clear planning leads the way and the panel of talented and committed experts that Inner Circle founder Matt Ritchey has assembled for Inner Circle members is formidable. 

Set your growth goals and build your tech and success team to meet those goals. Most of all, don’t try to do this in a silo.  The power of your network determines your net worth.

Inner Circle members get access to talent opportunities and connections that you won’t find anywhere else. We meet weekly to discuss what challenges you are facing and what will move the needle. 

Is Inner Circle Right For You?

At Inner Circle, our network is your network.
Kyle Dammann

Kyle Dammann

Kyle Dammann is an entrepreneur, venture capitalist, team builder, and automation expert. After a family member fell into a life-threatening addiction to prescription medication and his own experiences with plant medicine, he decided to dedicate his time and skills to legitimizing and accelerating the birth of the plant medicine industry. Kyle believes that access to nature’s pharmacy is a fundamental human right and that all adults should have safe, reliable access to these proven and safe compounds.

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