Where CTOs Have More Freedom: Startups and Corporations

Kirill entered technology through systems administration and never worked as a professional software developer. His path to CTO was a gradual expansion of responsibility. At a healthcare startup, he first led support, organized the work within his remit, and then volunteered to manage development. He joined START as a project manager; when part of the team, including the previous technology leader, left, he had an opportunity to step into the role. Over six years, the team grew from roughly 12 people to 150. He does not present this as a perfectly planned career ladder: chance, willingness to take on work, and accumulated experience all mattered. The transition changes how an engineer contributes. First, you find good technical solutions yourself; later, you help a team find them; eventually, you shape the organization’s ability to work with technology. Taking on limited management duties and seeking feedback can test whether that work is appealing before committing to a full role change.

Scaling required changes to processes as well as recruitment. Books gave Kirill a repertoire of approaches, but conversations with CTOs who had navigated similar transitions were particularly valuable. He arranged meetings, described concrete problems, asked about their mistakes, and adapted the lessons to his company. Roles in the startup remained broad: a project manager could also write detailed requirements, perform systems analysis, and coordinate several teams. A Python developer built the first in-house content encoder. Platform economics changed with growth too. START initially used external CDN, billing, and encoding services; later, supplier costs and limitations made it reasonable to build some components internally. New technical functions followed business and technology needs. The important qualification is that adding people is not itself the objective. A specialist or dedicated team becomes useful when a real problem can no longer be handled effectively by the existing organization.

The move to Zvuk reflected both accumulated fatigue and an interest in operating at a larger scale. Kirill encountered vertical reporting lines, horizontal relationships, and mandatory requirements whose purpose was initially unclear. He estimates that understanding the rules of the organization took about six months. The hardest adjustment was leaving behind the habit of personally fixing a technical problem and immediately seeing the effect. In a large organization, the CTO builds a system that can do that work through other people. This means understanding the CEO’s and product director’s expectations, listening to the team’s problems, and establishing relationships with managers one and two levels below. Authority has to be earned through actions and useful changes. Kirill invited the team to challenge his proposed solutions and examine the reasoning, while acknowledging that he would now handle some practices imported from his previous company differently.

One change involved building platform teams and spreading knowledge that had previously resided with individual specialists. In a small company, dependence on one person may be a conscious risk under resource constraints; at greater scale, it threatens the functioning of the system. Another challenge was the engineering career path. If management is the only progression beyond senior engineer, a company either loses strong engineers or turns them into managers to justify higher compensation. Zvuk developed a technical track that allows influence through expertise without necessarily managing people. The role still needs a business purpose: difficult problems, a clear domain, and a reason the expertise matters. Strong engineers help colleagues and the CTO develop; leaders should welcome people who understand particular areas better than they do. Alexander describes a related experience with staff engineers, including deep technical experts and people who carry difficult cross-team projects, with responsibilities distinct from promotions and regular people-management meetings.

In either environment, the CTO must understand money. Shipping speed matters, but so do operating, support, and development costs over one, three, or five years. Preparing a first budget forces a leader to justify infrastructure, staffing, and growth assumptions against product plans. Startup agreements can change quickly, and a founder or shareholder may make the decision. A corporation operates through distributed authority, portfolios of goals, and approval chains. The delay is not invariably measured in months: Kirill notes that some decisions can move within hours, depending on their scope. Significant changes usually require more evidence because a mistake can affect a large audience and the reputation of an entire ecosystem. Legal, security, architecture, and partner-company dependencies can block a launch that is technically ready. Freedom therefore includes the practical ability to carry a decision all the way into a working change while accounting for those dependencies.

Corporations also struggle to stop work that no longer creates value. Teams have an interest in continuing their projects, and ample resources can keep unnecessary features alive. Kirill connects the ability to discontinue them with culture and a leader’s willingness to make, justify, and carry through a difficult decision. Alexander adds an incentive-based explanation: a successful initiative may bring modest recognition, while failure makes its author personally accountable. Waiting for instructions can become a rational response. Exchanging useful practices between the two environments therefore requires more than copying processes. Startups can benefit from proportionate formalization, observability, and risk management, such as an incident response procedure with clear responsibilities. Corporations can benefit from autonomous teams, shorter experiment cycles, and personal accountability for results. Kirill’s closing career advice returns to the opening theme: pursue a broader scope of responsibility, develop your understanding of the business, and learn to see other people’s needs rather than concentrating exclusively on the CTO title.