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  • Malcolm De Leo

Guerrilla Infrastructure: The right people at the right time

Updated: Apr 13



If you look up the definition of Guerrilla you will find, "a member of a small independent group taking part in irregular fighting, typically against larger regular forces." (Google).


This concept has toppled governments, helped the less equip win wars, and in business, allowed smaller companies to own markets versus those who should dominate based on their massive resource advantage. That being said, many times the description of using guerrilla tactics is often about HOW you do things not so much WHO does it. Which brings me to a new concept in resource allocation that is, in particular, focused on companies trying to get off the ground. The concept is called Guerrilla Infrastructure and while it seems obvious, it is a principle for how a company scales that requires a reframed definition of who does the work at what specific time.


What is the definition of Guerrilla Infrastructure?


Guerrilla Infrastructure is the practice of strategically choosing to hire some fractional but experienced consultant specialists rather than all full time employees when you are entering a new market.


Why is this different than simply "hiring consultants"?


The concept of guerrilla infrastructure doesn't sound novel, but it is. Why? Because hiring consultants is something many people do before they decide to scale their business. And sure, what I am advocating is about hiring consultants to help scale your business, but it isn't quite the same. Because when a start up finishes testing the market and decides it is going to scale what usually happens is a race to fill key boxes in the org chart with full time experienced folks as fast as one can. You see, most really small starts ups I have dealt with either go without or go full bore. They don't really live in between. And the concept of guerrilla infrastructure is more about the leader recognizing that while they think they figured out the market when they are ready to go; they actually haven't yet. What guerrilla infrastructure advocates is that when you think you are ready to hit the market you might be better served mixing full time hires with part time experienced experts. This way you can have people you need to execute the blocking and tackling mixed with a group of people whose years of knowledge allow them to help you test and learn the market more quickly, expedite market penetration and avoid costly mistakes.


Getting real about where (and when) you need the help


As the person responsible when you are just getting started, dollars are precious. And like most new startups getting off the ground, you will usually start with a core team mixed between a few founders, a technical leader, some engineers and perhaps some junior folks. During the seed round, your team of 4-8 folks will be tasked with doing absolutely everything. Armed with a great idea, a prototype, a fundraising deck you are going to be really proud of and a lot of confident energy, you will quickly find out the journey has only just begun and the mountain you will have to climb is quite high.


So where to go from there? Obviously, you need to...

  • Drive revenue for your next round

  • Get the product market-ready and scalable

  • Create some sort of marketing collateral (blogs and social posts) to begin to attract leads

  • And you need to hone your go to market strategy, your pricing philosophy, begin to create your lead generation process and the list goes on from there...

But on that last bullet...that is when the ship can slowly move away from your true north if you aren't careful. Notice I don't say hire great talent and begin to scale the org chart? Going to market is where the danger lies and when the concept of guerrilla infrastructure is most appropriate. Where and when should you deploy this concept? First, let's delve into why you need to think about this...


Thought #1: Big Game Hunters vs. Coin Operated isn't a decision


This is an important moment in any startup's life. You've been funded. You launch your product. You begin to close some deals. And best of all, you are getting traction and encouragement to get the show on the road. Every CEO is faced with the same question; who do I hire when it's time to bring your first sales person? We need them to scale, right? This is a tricky question, because by all accounts you are going to be faced with two choices; the Big Game Hunter or the Coin Operated Doer?


Who is the Big Game Hunter?


Because most startups envision their company being the next billion dollar business, it is easy to believe that the perfect sales leader will be the one who has scaled other companies by building big sales teams and drives big revenue. They are the Big Game Hunter. This person is super experienced sale leader who can "take over" from you and begin building the front end of your sales organization. They can, if given the right product with a great market fit, scale your business. They are who you are looking for. But should you hire this person if you hiring the first sales person? It's a personal question that much be answered by each leader. So why should you? Because if you really do have a tiger by the tail they will scale your company in the way you hope. In addition, the Big Game Hunter is a strategic thinker who you do need to scale the business. But why shouldn't you hire them? Because the Big Game Hunter usually won't sell your product themselves, their time of doing their own deals is often long gone and they are mostly interested in scaling the sales process while those they hire do the selling. They inherently need to burn your resources to do their job and while you think you are ready, the odds are you are not.


Who is the Coin Operated Doer?


Your other option with your first sales hire is someone more junior but capable of selling. This seems like the more logical person to hire when you are starting your sales effort. Hiring someone who is a pro but more junior is certainly another way to go. In a sense, the coin operated sales person is the person who can operate the sales process for you while you sell your expertise and knowledge. It seems like a good marriage of convenience but is it? In this case the coin operated doer represents building the rigor you need but without the strategic sales thinking; that is up to you. There is nothing wrong this being your first hire, but you need to be aware that a coin operated sales person will be bringing the tactical expertise you need, but you will still to do almost all of the strategic heavy lifting.


So what is the problem with this binary choice? Your choice is very dependent on your ability to know yourself when it comes to sales. As a CEO you have to get real about your sales skills, how confident you are in your go to market strategy and most importantly how good a product market fit you truly have. All startup CEO's are going to be pushed to sell as they get their company off the ground, but what is important is centered in thought #2. Do you know yourself and the difference between closing deals and being a good sales person?


Thought #2: Closing deals and being a good sales person are not the same


This is a classic startup go to market mistake. And it usually rest squarely on the shoulders of the founders (usually the CEO). Many new CEO's, who are great risk takers, are brilliant, are passionate, are driven to succeed, are visionaries, are aspiring great leaders but ARE NOT a trained sales people. Armed with a great idea and boatloads of passion the start up team's number one job is to close business. And usually this means that those 4-8 first employees who are tasked with doing everything must learn on the fly and do it themselves.


And in some cases they are natural born sellers. And in nearly all cases they will figure out how to close business. But this is where the schism begins. There is a difference between closing a deal and being a good sales person.


Closing deals means getting people to say yes to your pitch. Being a good sales person means you are selling with an eye towards creating a repeatable and scalable process that can be executed by others without needing special technical skills, talents or extremely deep understanding of the product being sold that relies on specific expertise.


Many companies first deals occur because the customer buys the brilliance of the founder. They do this because of CEO's ability to answer every single question helps build the trust they need to say yes. When they buy they feel like they have just hired the smartest person in the world to help them solve a distinct issue they have in their business. But if that is why they are buying something is that scalable? No, it isn't and when the CEO thinks they are a good sales person because they convinced someone to buy into their vision early, they often make the mistake of thinking it's time to roll. And when people think with a few deals under their belt they can start going as fast as the VC wants them to, they begin to open themselves to risks they can't see. Don't make this mistake. Closing revenue is great, but can you teach someone else to do the same? If you can't, you need help from someone who can think holistically about how to universally sell to the markets and verticals you care about. You need to check your ego at the door so you don't sell science experiments that can't be renewed. You goal is to sell repeatable and scalable use cases that can be applied across verticals to show your investors you have a business worth putting more money into.


So now ... question is are you really as ready to scale as you thought you were?


Thought #3: You think you are ready to scale but are you?


This seems like a mundane thought, but I put it here to make sure you take a step back and really consider this. I have seen many companies come out of stealth mode thinking it's time to role because they have closed a few deals, seem to have customers who are happy with the product, and even have some slight traction on the market. There are a few questions to consider about the market you are entering before it's time to role. I wrote about them in detail here, but I will highlight them again


  1. Can your customers articulate what you are selling them? This means if you are selling widgets to go to the moon do they understand that and can explain that clearly?

  2. Do they have ways to apply your technology to their business? You might have to help them, but if they can define your space and tell you how it applies to their business that is a good sign.

  3. Do they have people who are responsible to bring it to life? Articulating a new concept to you and telling you how it applies is great, but is there someone to operationalize it. If not...none of this would matter.

Why is this so important? Because you might be selling to one part of the market (or specific vertical) where the answer to all these questions is yes and then you make the mistake that the scale you envision in another vertical isn't there. Companies assume one vertical a scalable business makes. It does not. This simple market maturity rules are a critical miss of many leaders because to most companies that product is as good as you think it is when you cooked it up. Unfortunately, most leaders forget to think like their customers who have very different interests when it comes to new technology integration. Take a real step back, ask yourself how good is your product market fit? I bet it isn't as perfect as you think. If it was, you would hockey sticking without trying. We all dream of that, but the stats show that only 5% of startups make it. Don't forget this stat as you dream of that massive exit or IPO. Market maturity is often illusive, don't mistake your passion for a market that is still learning from you how to mature.


Thought #4: Fractional power is exponential not linear


What is the value of experience? Some would say those who have been around the block too long are outdated, stodgy, and often less valuable than someone how is fresher, less jaded and more open. Actually, this is probably true. But we aren't talking about either or but both. The argument for bringing in fractional but highly experienced resources is about bringing all those additional experiences into your business to increase the likelihood that "been there done that" thinking can actually help you make better decisions faster. Mixing full time less experienced employees with more experience fractional ones is a great way to get the best of both worlds.


Startups need both people excited and passionate to help drive the ship faster with people whose wider purview help steer the ship most quickly to the right place. If you do the math the cost of this mixture is probably equal, but the power of having really efficient and experienced hands helping the crew steer the ship is exponentially better. Guerrilla infrastructure allows you to bring in the right people in the right places where the gaps in your crew exist to accelerates and drive decision making in a more strategic experienced way. This will allow your full time employees the space to drive the business everyday without the distraction of taking on roles they are not trained for.


The point can be answered by this question. If you are getting ready to scale and you have a small team most of whom are driving the business based on your passion what are the chances you will make an unforced errors because of their lack of experience? It can be pretty high. By having some folks in areas you need to help you see pitfalls that have been run into before can be a great way to make better decisions, test the market more quickly and as I shared above test the market in ways sheer brute force will miss. This mixed resource concept will create finesse in your execution that can be lacking as you hope to reach the hockey stick.


Why does Guerrilla Infrastructure maximize and extend your runway?


Many of the thoughts above about Guerrilla infrastructure seem to be focused on only sales and marketing. As I shared in the last section, this idea is about bringing the right fractional resources to the right part of your business at the right time. The sales and marketing focus is centered around the high likelihood that many tech startups founders are technical and not business focused. As someone focused on efficient expansion of the front end in a purposeful way when going to market, these thoughts demonstrate some of the choices one makes between having the back end resources built but not the front. That being said, some companies that have business CEO's need a fractional CTO to guide product development. It doesn't matter. Guerrilla infrastructure is about having the open mind to fill in your gaps with those partial people who fill extremely important holes in your knowledge and leadership until you figure out how to launch for real.


The beauty of this concept and how I like to think about it is this...Guerrilla infrastructure is a phase of your business where these consultants can fill the important gaps you need to succeed. Who they are and when you bring them in can vary and evolve, but being aware as a leader that you need them is the key. Think broadly about those fractional resources. Make sure you realize their value as a strategic weapon and not a tactical one to fill execution gaps.


If you are open to new structure of scaling wonderful things can happen.

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