The Intrapreneur’s Dilemma

When someone tries to innovate within a traditional organization,
few will understand what he/she is doing,
but everybody will understand who is a trouble-maker.

After the innovation has been embraced by the organization,
few will remember who started it,
but everybody will remember who was a trouble-maker.

This is the dilemma encountered by many intrapreneurs -
they risk punishment for success.

~ David Nordfors | President & Co-Founder IIIJ


The Intrapreneur’s Dilemma

Companies are heavy: thick with layers of management, columns of workers, and sticky procedures. Altering the direction or just making an impact within a company takes tremendous energy and resources. It is the nature of a mature organization to support its core mission and business model, not destroy it. Startups are light: thin and airy in terms of structure and organization. Changing direction is easy and is in a startup’s nature as it seeks to find a business model and market. Launching a startup inside a company (intrapreneurship) is thus extremely challenging. Intrapreneurs live inside the belly of their corporate parent but must not feel captive (which is easy) but rather opportunistic as they are not alone and are surrounded with resources, channels, and cover. Yes this comes at a price but everything is a trade-off — just ask a startup founder what their salary is.

An intrapreneur for this essay means someone or some small group that initiates change or experimentation on their own — with no mandate or dedicated resources from their company. While many companies have platforms such as “skunk works”, R&D labs, innovation centers, and so on — true intrapreneurship is the pursuit of change from within without a predefined ecosystem to explore such change. The formal innovation initiatives have their place and provide tremendous value but the pure form of intrapreneurship is the focus here and is what David speaks of in the title quote.

Me? I have been an intrapreneur for most of my professional life. I have enjoyed tremendous success as well as infuriating failure as an intrapreneur. In fact for a moment in my career I was an intrapreneur-for-hire in many respects as organizations hired me to define and catalyze change in some fashion. But a for-hire scenario is much different than an organic intrapreneur. Let me share a quick story.

Around the turn of the millennium the legal staffing industry was in its glory days. Law firms had massive amounts of work, were flush with cash and wanted more. I was leading the DC office of a leading legal staffing company — Ajilon, now Special Counsel. My focus was on temporary staffing — specifically supplying temporary lawyers for large litigation or M&A projects — both of which were in great supply at this time. There was so much work and the projects were getting so large that it was common for the local talent market to dry up. This talent pool easily was into the several thousands. Agencies based in DC began recruiting from Baltimore and Philly and even Pittsburgh. On many of my projects I even had dozens of lawyers from the west coast commuting to work in DC for several weeks. It was insane and fun.

With this acceleration came scarcity and quality erosion. Some agencies were not even interviewing or meeting their candidates in the feeding frenzy for talent. At first law firms did not realize or care. Eventually though this market had so much work that temps would leave projects mid-way to join another project that might pay a bit more, last a bit longer or have better working conditions. Speaking of conditions — it was common practice at the time for these projects to be housed in Class C real estate — often subterranean and 100% artificial light with folding tables and chairs where the temp lawyers would sit for ten, twelve or fifteen hour shifts. It was not pretty.

Law firms typically “managed” these projects themselves — everything from the work-product to the logistics (meals, schedules, furniture, technology, etc). The youngest lawyers in the firm — often with only 1 to 2 years of experience — were put in charge. With no business, professional, management or even legal experience, these young lawyers were tasked with keeping the project on course and under control. It was unsustainable.

Around this time I had begun to experiment with how I was dealing with my clients. I was in sales and so being close to my customer was a key to my success and my bank account. More than this motivation though was my eagerness to rid myself of the friction associated with the current business model that dominated my industry. I disliked the “body tossing” or throwing unvetted temps to my clients because quite frankly I knew I would have to fire these same people in a week or so. I also did not enjoy the complaining and whining I got from the temps as they looked to me to cure the problems that were outside my control — like work environment or lack of clear management. I was empathic but powerless. Or so I thought.

I had small lean team around me to help organize and run my book of business. There were only four of us but the amount of work we could get done was amazing in terms of our peers inside and outside the company. We each felt the opportunity to change the way legal staffing was done. Our team looked and acted like co-founders each with distinct roles but often these roles blurred into one another, as we all would jump into a challenge to solve it together. There were plenty of late nights, weekends, beer and pizza and so on as we scrambled to deliver our expanding new services to our clients. We were not software hackers but service hackers as we worked creatively to solve unique issues and crack human and process challenges. We were removing the burden and cost of running these large projects incurred by our customer law firms. We were developing deep skills and project management techniques to take on the loads of administrative, logistical and human capital work that needed to be done. We were designing new services and a new business model for the legal staffing industry.


few will understand what he/she is doing,
but everybody will understand who is a trouble-maker.

While we did not purposely set out to create a captive startup — in essence that is what we did. Our efforts led to capturing $25 million in revenue and robust margins within eighteen months — an unheard of accomplishment inside the company. We did this through experimentation — small bets with plenty of failures and mounds of learning. Leading the team and having lone P&L responsibility for it, it was my job to sell our “new” services not just to clients but also internally to my CEO and CFO. While we were bringing in high margin dollars we were also taking bountiful commissions — a couple of us anyway — as we were on sales compensation plans (this was my Incentive — see below).

Our business activities were also creating friction inside the company, as we needed high bandwidth and new methods to accomplish tasks that had pre-determined “hard-wired” workflows and process — like payroll, benefits, time keeping. Adding to this friction, we began charging for our services differently and added new services that did not exist prior. Accounting, human resources, and senior management often reached out to me with demands for conformity and compliance. My intention was not to break rules but the simple fact was that our team had created such velocity and acceleration in our new business that we needed to bend — if not break status quo internally simply to get the job done and our clients satisfied.


few will remember who started it,
but everybody will remember who was a trouble-maker.

We were truly successful with our new model. The legal staffing industry changed significantly as part of our efforts and what is today called “managed document review” in the ediscovery and staffing world has much of its origins in the model that our team created. The lessons learned from this experience are powerful and demonstrative of what life is like as an intrapreneur.

I did receive multiple awards for innovation and gained the recognition as a leader but my role always had an invisible asterisk beside it to note that I was not a “company man” but rather a rule breaker. I cherished that label then as I do now. But I would come to pay a price for this success.


they risk punishment for success.

After the tremendous success of our new business model inside the company and the industry, our corporate leadership began to embrace the value we were bringing and so wanted to extend control over our team and activities. This could have been a powerful amplifier to our efforts but due to the nature of most corporate environments, including this one, it was instead a stifling and hostile approach. Compensation plans were under serious threat. Resources that we had hacked were now being over-extended as the company looked to scale our services without the proper understanding of it. Others in the company began to sell our new model but were not trained to deliver in terms of quality or capability. I was brought in on a number of projects that other offices and sales people had sold but were under-delivering on. These diversions made my own business efforts suffer and I had to rely on my team more and more to step up and manage in my place. The clients were getting upset. Internal staff and resources were getting frustrated with mounting special challenges in adapting to the new business model. The rest of the industry was catching up fast. My team was exhausted and growing in resentment as they saw our success get diluted and downplayed over and over again. It was becoming toxic.

My team and I ultimately left the company as we saw the value of our efforts get compromised time and time again. Our company simply thought that scaling this new business was as easy as selling more of it. We wanted to see it succeed in the way we knew it could and should. I found a younger more aggressive company that craved the type of innovation we had built and so joined them. My prior company quickly realized the ramifications of losing my team and so filed a lawsuit against me for well over $20 million. The rest as they say is sealed in settlement papers.


This story is not unique. Countless intrapreneurs have found themselves in similar circumstances. It is because of this that companies have established programs and efforts to help alleviate the burdens faced by internal innovators. In other cases, companies have outsourced their innovation through such platforms as Innocentive. Recently innovation has become even more of a trend as more companies have learned that their typical operating environments does not allow for much innovation or intrapreneurship. To those individuals inside companies that have not taken these steps — beware — you will need strong conviction, uncanny business acumen, and a laser focus on your goals to achieve what you are attempting. And you will need one hell of an incredible team to make it work – no matter how small.

Here is what I know it takes to be a successful intrapreneur — success being the execution of building and launching a new innovation inside a mature company. Career success for the intrapreneur is a different thing altogether and is heavily influenced by the intra’s ability to adapt, leverage, and survive. The following “traits” have been defined based on my initial work shared in the story above, numerous subsequent engagements and from trading notes with others.

Incentivized: Most intrapreneurs have a clear incentive for doing what they are doing. For many it can be money – especially those that are in sales or marketing. Their compensation plans are often elastic enough to provide adequate additional cash to make the effort worth it. Those that do not have a direct link to making more money often will have a passion or a strong sense of customer loyalty. These attributes can actually be more powerful than money, as was in my case. My checks were nice but without a conviction to make the business model better and the loyalty to my customers, I could have easily made decent money without all of the associated headaches with being a troublemaker. The point is, there must be incentive or nothing will happen. That is why organizations that lack any sense of encouragement coupled with enticement need to build something more substantial than a suggestion box. Nobody works for clear plastic award trophies alone.

Subversive: This word tends to have a negative connotation so perhaps rebellious would be better. That said the intrapreneur does need to have a sense of anti-establishment tendencies. If the current business is doing all the right things, there will be no need for the intrapreneur. Therefore, the intrapreneur tends to see the gaps, confounding processes, and oppressive management of their current environment and works against them to accomplish their goal. Mind you, this subversion is not directed at hurting the company but rather to strengthen it despite itself. The vast majority of intrapreneurs have a neutral-to-positive outlook on their company and want to help it. If they wanted to hurt it, they would simply leave. In my case, I did picture a long career at the company and only left after it began to hurt me deliberately – not an uncommon result unfortunately.

Unrelenting Focus on the Customer: This is a no-brainer. Most, if not all, intrapreneurs see a customer that is either neglected in some way or ignored by the current business model of the company. They see that there is a better-defined problem that they can solve rather than selling the same old product or service for old, ill-defined, or irrelevant problems the customer may have. The saving grace for the intrapreneur is the early adopter customer – the one that is willing to test, measure, and learn alongside the intrapreneur and most importantly pay for doing so. There are no such things as pilots or betas for the intrapreneur-without-a-company-mandate. Co-creation is key here. Without a paying customer the intrapreneur does not stand a chance.

Lean Team and Analytics: Intrapreneurs have a huge challenge if they want or must work alone. They will need help – from “co-founders”, executive sponsors, administrative heroes, and customers – at least one. As the innovation grows, the intrapreneur must be on alert to “convert” those they find within the company that can be helpful. For executive sponsors, nothing works better that clear ROI analysis or some form of benchmarking for success. Capturing and analyzing the build process will be essential to making the case later on that this innovation will work. This data will also help quantify the investment of time and effort put in by the intrapreneur to demonstrate that the innovation is not a substantial deviation from what the intra’s actual job is. Further, since most mature companies are run based heavily on Key Performance Indicators (KPIs), it is in the intrapreneur’s interest to begin shaping and defining new KPIs relevant to their innovation

Being Captive (aka No Escape Velocity): Escape velocity in the external startup sense is used to describe the stage at which a startup has reached a point of sustainable growth. It can survive on its own. For the intrapreneur there is no real escape velocity other than when the parent company begins to monetize and integrate the intrapreneur’s invention into the core business model. While there is escape velocity for the new product or service, most intrapreneurs are marginalized or otherwise limited in their ability to seize the moment and ride the wave of success they built. The intrapreneur must be aware of this and prepare both their ego and emotional ties to their creation. Most likely they will not be allowed to “follow” their innovation inside the company.

Okay with being alone: Being an intrapreneur is the worse kind of alone: unlike startups founders for who there is a huge community, there are few if any meetups or peer groups for intras, no slick and cool conferences, no content or media companies covering this area. This lack of peer network can be isolating at times and company peers will more than likely ignore intrapreneurial efforts, shun them or resent them. The team must be able to work in conditions that often feel isolated and exposed. Many in the company may be waiting for the intra to fail. Others may simple downplay efforts. Nevertheless the intrapreneur must not measure their satisfaction based on anyone else initially – only the customer.


So why even attempt intrapreneurship inside your company? Why risk the alienation, misunderstanding, and turmoil to build something valuable for your company not yourself? For me it has always been the sense of adventure and compelling motivation to build. Working inside a company has many challenges but it also has many advantages like infrastructure, platform, and access to markets. Often, an intrapreneur would be unable to leave the company to build their innovation on their own as an independent startup. The parent company provides a paycheck, security, and resources while also presenting significant challenges as outlined above. The choice to pursue an innovation must take into account all of this. The intrapreneur can easily lose much in terms of their career and job satisfaction all in an attempt to create value for their company. They will be trying to push their company forward while being pushed down by this very company. But if they are successful the riches of experience and leadership (and sometimes money) are theirs. That is in essence the intrapreneur’s dilemma.