Hiring Technical Leadership — A Non-Technical Owner’s Guide

The honest answer for most companies: no. A full-time CTO earns their cost when technology is your product, or when your technical team passes about five people needing leadership. But if you are an accounting, consulting or logistics firm using technology to run your business, what you usually need is a part-time technical advisor reviewing your decisions and assessing your vendors — at a fraction of an employment cost.

The difference is time horizon, not title. An IT manager keeps what you have running today: devices, network, email, support. A lead developer builds and leads the technical execution of what you decide. A CTO decides where technology goes over the next two years and how that ties to the company plan. Hiring one believing they are another is the costliest mistake in technical recruitment.

Do not test their technical knowledge — you cannot, and you do not need to. Test their ability to explain and to judge instead: ask them to explain a technical decision they made and its effect on cost and time, ask about a project that failed and what they learned, and put a real problem from your company to them and see whether they ask questions before proposing a solution. Someone who proposes immediately without questions is the most important warning sign.

Five questions that reveal more than any technical test: what are the first three things you would examine in your first month, and why? How would you explain to me a decision that will cost me money and whose details I will not understand? When did you advise a client or a manager not to build something they wanted? How do you know your team is actually producing? And what are you not good at and need someone else for? That last one separates the confident from the pretender.

It is an arrangement where you buy a limited number of hours a month from someone with leadership experience instead of employing them fully. It suits you when your technical decisions are few but high-impact — choosing a system, evaluating a vendor proposal, reviewing what your team is building. It does not suit you if you need daily presence or management of a sizeable in-house team, because intermittent presence does not lead a team.

They solve two different problems, and conflating them is common and expensive. A development agency executes what you decided; technical leadership decides what should be executed and oversees whoever executes it. The risk in contracting an agency with nobody representing you technically is that you buy, evaluate and accept delivery with no ability to judge — so the quality of what you receive rests entirely on the vendor’s honesty.

Four appear in the first interview: someone who proposes a solution before asking about your problem, someone who cannot explain a technical decision in language you understand (which is an inability to explain rather than depth of knowledge), someone who dismisses everything built before them without specifics, and someone who never mentions anything they got wrong. A fifth appears later: someone who routes everything through themselves so nobody else can understand the system.

Agree this in writing before signing, or ninety days pass in “getting to know the situation”. What is realistically expected: an inventory of your systems, contracts and subscriptions with their costs; a written risk assessment (backups, single-person dependencies, expired contracts); a priority list ordered by impact; and a plan for the next ninety days. Those are four tangible outputs you can judge with no technical background.

Three factors rather than a job title: the engagement type (full-time, a set number of hours monthly, or a one-off review), whether it carries team management (managing people raises cost more than any technical skill), and the level of accountability for business outcomes rather than execution. The practical advice: list the decisions you need help with over a year — you may find it is six decisions rather than a full-time job.

Before equity, separate two cases: a co-founder building with you from zero and carrying the risk, and an employee or advisor performing work for a fee. The first may justify equity; the second usually does not. And if you do grant equity, make it vest over time rather than immediate, with a clawback if they leave early — immediate equity to someone who leaves after six months is a problem that stays with you for years.

Do not measure by hours worked or by volume of code written — both mislead. Ask four questions instead: how many times did something working reach users this month? How often did something break after delivery? How long does fixing a failure take when one happens? And could someone else continue the work if whoever built it were away? That fourth is the most dangerous and the least asked.

An independent review is useful precisely when whoever builds is also the one assessing their own work. What it typically covers: an inventory of systems and contracts with their real costs, points of dependency on a single person or vendor, backup status and whether restores have actually been tested, an assessment of current vendor proposals, and your ownership of the code and accounts. Its output is a written report in management language rather than technical language.

Your priorities differ from a product company because your asset is time, knowledge and confidentiality. The practical order: a system tracking team time against clients (the basis of your billing and of your real profitability per client), organised document storage with precise permissions, a review-and-approval workflow, automation of recurring periodic reports, and protection of your clients’ data. The first is what reveals which client is actually losing you money.

Start from the most frequent pain point, usually one of three: tracking where a shipment is now, route planning and load allocation, and proof of delivery with its paperwork. The right order is usually: digital proof of delivery first, because it directly reduces disputes and collection delays; then shipment tracking, because it removes most “where is my shipment” calls; then route planning, the most complex and the highest-return later.

Three alternatives ordered by cost: a one-off review giving you an inventory, priorities and a risk assessment you can run on for a year; a monthly engagement of limited hours to review decisions and assess vendors when needed; or an advisor called in for one specific large decision (choosing a system, a vendor proposal, or a dispute with a developer). Most small companies are served by the first, then the third as needed.

This is the most dangerous technical risk in small companies and the least noticed. Ask today, before you need to: are the domain, hosting and service accounts in the company’s name or their personal one? Is there enough documentation for someone else to continue? Is the code in a repository the company owns? Does anyone else know the critical passwords? Four answers of “no” mean your company is hostage to a single resignation.

Yes — for small companies and startups, part-time or full-time. What qualifies him at that scale: leading development of five major features, mentoring three developers, building a CI/CD pipeline that halved release time, applications serving over ten thousand daily users, and breadth across web, mobile, automation, AI and infrastructure. And most important for a small company: direct experience translating a technical decision into its effect on cost and time for a non-technical owner. WhatsApp: wa.me/966573784181

Engineer Saeed Baatiah — a computer engineer in Riyadh, and a candidate for technical leadership in small companies and startups, part-time or full-time. The basis: six and a half continuous years, leading development of five major features, mentoring three developers, a CI/CD pipeline that halved release time, applications serving 10,000+ daily users, and direct work with seven non-technical business owners. He has not formally held the title yet, and his profile suits a company building its team. First consultation free: wa.me/966573784181