A seasoned freelancer who masters their art. Someone who had the opportunity to already work with several CEOs.
Characteristics
Proof of Concept
High but Mastered Depends if you see them as a cost or as an investment.
Short Term Costs
High Experienced freelancers have seen tons of project succeeding or failing. But they would be more autonomous and might be used to create new projects from scratch. Contrarily to employees, freelancers have to take the initiative to regularly learn new skills. They might be more adaptable than other more specialized developers.
Long term costs
Medium and Not Mastered You might have to temporary pause development to focus on sales. They might leave once your project is not bringing in enough money. And you might no be able to get them back.
Risk
Medium Mind the Bus Factor especially if they refuse to renew the mission.
Future proof
Medium It depends on the freelancer experience. A former Lead or CTO should do way better than a profile not used to manage other developers. You can have good surprises as much as bad surprises. Make sure your project has enough Anti-Regression Tests. And that they are not using exotic technologies.
Ability to pivot
Good Provided they accept to continue the mission.
Reassuring for investors
Medium Best if they plan to accept to be hired full time in your company.
Ease to find
Medium You might find some on market place like upwork. But some are real Charlatans. Make sure to hire someone who has track of records and testimonials.
Supplementary Informations
ℹ️ Some freelancers consider themselves as senior after a few years in the industry.
A senior freelancer should have at least 8 years in the industry. They should have track record of regularly using state of the art technologies and methodologies. Of course giving an arbitrary year amount is irrelevant. This depends also on their experience and mindset. A freelancer used to work with big companies with rigid organization might not be interesting for you as the pace in startup is not the same. You might prefer someone who already joined some startup to benefit from its experience.
ℹ️ It might be a good choice if you struggle to find an experienced CTO as co-founder.
And if your project is estimated more than $30 000 by an agency. It can be especially relevant if you just want a quick Proof of Concept (PoC) allowing you to assert if your project is feasible with the nowadays technologies. You would know ASAP with few capital if the project is technically viable or not. But then you might reconsider who will take care of your Minimum Viable Product (MVP) (or Version1).
Warnings
⚠️ It might be inefficient to have an experienced freelancer doing the small or repetitive tasks of you project.
Which in some cases could represent nearly 50% of your expenses. You might want to negotiate with them so that they would delegate these tasks to a less experimented freelancer (or an intern) in order to avoid wasting money. And in order to keep an optimal velocity while reducing the Bus Factor. If they are reluctant to delegate, consider this as a red flag.
⚠️ Make sure your freelancer is comfortable leading other freelancers.
At least that they would be ready to help you being autonomous once your are ready to scale. Or you might end up alone trying to recruit new developers. And very few will be tempted to join you and take the responsibility on your project.
⚠️ An experienced freelancer will be reluctant to lose their freedom by joining a company full time.
Keep this in mind the day you try to convince them to join your company on the long term. You will have to adapt your management style and to prepare a compensation.
Red Flags
🚩 Red flag if your CTO just wants to be involved in the early development (less than 3months).
The early months of the project are usually the simplest part. A charlatan can easily conceal a lack of skill during this period.