Hire A Gap Filler
Early on as CEO of a technology startup you will need to do 100 tasks that are not existential to the company, but still important that you get done. Tasks may include:
Finance and accounting (setting up payroll, 409(a), finding a part-time accountant etc.),
Office setup (finding office space, decorating it, getting furniture)
Ongoing tasks like ordering food and lunch, team outings and the like
Additionally, there may be items where you need help as CEO or someone to help manage certain day to day areas including:
Basic business development support (deals)
Basic marketing work (early product marketing such as sales collateral, Twitter and Facebook account management, PR support etc.)
Early sales or partnership account and relationship management
Fundraising or partnership support (pitch decks, financial summaries, data requests)
Employee onboarding, welcome packages, logistics
At a larger company you would likely have one or more people for each area. For example, you would have a CFO, a facilities person, a business development team, marketing, and HR. In a 5 person startup without product/market fit, it might be premature to hire any of these functions on a full-time basis. However as CEO you would optimally delegate all these items. While some startups split the above tasks up between the various co-founders, another option is to hire a gap filler.
Hiring A Gap Filler
Depending on the seniority of the person and the expected evolution of the role, your gap filler could be a COO, a "chief of staff" for the CEO, or a junior business development, finance, or operations person. You could also split the role between two people - for example a talented executive assistant or finance person for the office and accounting setup and a talented business generalist for the BD, sales, and fundraising tasks.
The common traits you would want in someone filling the gaps include:
Detail and process oriented. In order for many of the items above to be done well, you need someone who can manage a process well and catch any items or errors early.
Follow through. The purpose of this role is to prevent items from falling through the gaps. You want someone who can take on a task and see it to its conclusion.
Ability to context and mode switch. The gap filler will take on a wider variety of functional tasks in a given week. They must be able to work on an office search for an hour and then a partnership meeting the next. This means fast mode switching and a generalists skill set.
Fast learner / willing to deal with ambiguity. Given the breadth of the role, the gap filler must learn quickly on the job.
Will eventually be happy to focus on one thing. As a company scales, the gap filler will eventually be replaced by multiple people. They should have one functional area they will eventually migrate to such as customer support, business development, marketing, product management, or other areas. This area does not need to be set in advance. However, optimally you will either have a long term plan in mind for the individual or they will naturally find the right part of the organization to fit into as it specializes and scales.
Founder trust. Great gap fillers tend to earn founder trust early given the competence and follow through needed for the role. This trust can later translate into outsized roles as the company scales (assuming the gap filler can scale with the company).
Gap Filler Example
Salar Kamanger, employee #9 at Google is a good example of someone who started as a gap filler and eventually went on to run YouTube. Salar joined Google straight out of Stanford undergrad with a biology bachelor degree. He did a series of odd jobs the founders needed help with - including early legal and finance, writing Google's first business plan, and eventually migrating into product management. Salar had a stellar career at Google due to his competence and intelligence as well as the relationship he built to Google's founders and early team.
Gap Filling As A Startup Scales
Once a company exits its raw startup phase and has product/market fit, it is often useful for the CEO to hire or promote someone into an executive version of a gap filling role. This person ends up as a company "fixer" or scaler. They may have a number of different titles such as COO, VP Product, VP Corp Strategy, etc. but in all cases in reality they do the same thing - fill in at the executive level for multiple company functions at the CEO's direction. This executive gap filler helps build out or run functions until a proper full time executive can be found for a given area. More on this coming in another future post.
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