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I am working with former Finance, HR, Marketing and Sales Directors as well as CIOs / CTOs and a variety of other experienced professionals to build a Portfolio Executive workstyle.  I have come to believe that there is not a ‘one size fits all’ answer to how big a company you should target for your services.   For each of these different roles, there is a different business life stage at which organisations begin to recognise the value of director quality support. Whether they are right or wrong is not the point; you have to address the market as it is.

Avoid the micro trap

As you build your portfolio executive workstyle, you may come to believe you are an entrepreneurial start-up in your own right.  You will gravitate to the community of entrepreneurial start-ups and you may start to think that the easiest people to target are the people in this community.  But too often these are micro businesses i.e. less than 10 people and a turnover of less than £250,000.  I firmly believe that they are not the right place to start with a Portfolio Executive proposition for three reasons:

1)    They can get a lot of free advice – you don’t want to compete with ‘free’

2)    They do not usually have the money to really value the time that you want to offer them – you will be driven to under-price your offer

3)    It usually takes at least 2 years for a start-up to work out what business they are actually in – until they know this you will get sucked find what you bring has to be re-invented each time strategy changes.

The only exception I would make is if your client is an established business leader or entrepreneur who has already built a business and now is going to do it again.  They understand how business works.  They have clarity about this new business within the context of their other businesses.  They have the potential to be an informed and intelligent buyer of your services.

Right size for a Finance Director (or HR Director) – starting small

Let us assume that your client is a business that is more than two years old and has more than ten people.   Are they big enough for you to really create value as a Portfolio Executive?   It depends on what professional expertise you are bringing to them. So, let us start with the most obvious role: the part-time Finance Director.  Lots of businesses will have an external accountant that is focused on compliance: tax returns get done on time, VAT paid and end of year accounts filed.  They may also provide bookkeeping services. What that accountant and bookkeeper will not usually do is provide regular, timely, appropriate management accounts inform the management of the business. As a part-time Finance Director, you are looking for a business that is mature enough that they need to actively manage their cash-flow, they have some kind of pattern of working, probably have a part-time bookkeeper and they have a compelling need to better understand the financial facts of the business.   I would suggest that that starts to become relevant when the business has a turnover of at least £1/2m  , and probably £1m. They should be prepared to engage you for at least two days a month and pay a day rate in excess of £1,000.   Part-time Finance Directors can engage with relatively small businesses with a relatively small amount of input and can create value quite quickly.

However, if you are particularly interested in bringing corporate finance capability to an organisation then the threshold may be rather different.  Fund raising, acquisitions and disposals will become relevant either because the business has massive ambitions to scale or because the business has got to a life stage where financial engineering is a critical part of the path to growth.

For HR Directors, I think that there is a similar kind of threshold, although the risk for HR Directors is that they can get involved in compliance issues only.  You really want the business to be pursuing growth so that recruitment and talent development are significant issues.  Your target sector will also have an impact – for example, hospitality has usually has high turnover, IT usually has to compete for talent – both issues increase the value HR can bring.

Right size for a CIO – thinking big

Let us look at the other extreme: a CIO.  When is a business large enough to need a CIO? Businesses without a CIO may have started with an in house IT Manager and then moved to outsourcing to an IT services business.  An IT services business is well sorted to the basic stuff.   Perhaps they were using one or two business applications (maybe a CRM, an accounting system or specialist industry related system).  Now have two or three significant applications; they have a basic infrastructure of networks and PC’s and printers and tablets and so on.  But, they are not using IT for competitive advantage. Their technology is just maintaining business as usual: basic infrastructure being managed as such.

For me, the point at which a CIO becomes relevant is where the organisation is big enough and significantly mature that they recognise that they should start to use IT as a source of competitive advantage.  As a CIO you can make a real difference: you may start by helping them get better value for money for their current services. More importantly, you will establish an IT strategy for the next three, five or even ten years with a commitment to building competitive advantage through IT. You will look at the applications strategy.  You will examine the potential of emerging technologies such as virtual and augmented reality, block chain or artificial intelligence.  You will set out the road map to a digital future.   Setting aside fully digital businesses (for which the CTO is probably leading this effort) you will want to target businesses with a minimum 50-200 staff and a turnover of £5m-£100m.  In some sectors, the Finance Director has taken responsibility for IT and they can value a part-time CIO when they are even larger.

Right size your pathway to success

Picking the right size for your Portfolio Executive clients is really important. Avoid the temptation to start too small.  Avoid the temptation to start too big. You want to find that ‘Goldilocks’ size, not too big and not too small, where you can make a real impact, where the organisation is mature enough to value your services, and where the organisation is not so big that they are going to consume you as a full-time person.


Charles McLachlan is the founder of FuturePerfect and on a mission to transform the future of work and business. The Portfolio Executive programme is a new initiative to help executives build a sustainable and impactful second-half-career. Creating an alternative future takes imagination, design, organisation and many other thinking skills. Charles is happy to lend them to you.