Seven Phases of a Fractional CTO Engagement (Part One)

As a startup founder, working with a Fractional CTO (fCTO) provides a number of advantages which ultimately result in a greater probability of success when establishing your technical product and team.

Let's follow Jane, a seasoned Fractional CTO, through a typical engagement with a early stage startup that is building a SaaS application and is looking to hire their first engineering team to scale feature development.

Discovery: Company History, Aspirations, and Technical Review

When Jane arrives on the scene, the first 2-4 weeks are spent meeting with the current founders and key employees in the company. Understanding what the founder / CEO is building, their motivations and vision, history of the company to-date, SaaS metrics, and successes and challenges on the journey are a few of the topics that give Jane a baseline understanding of what the company has achieved as well as some initial areas of concern that she will want to explore further.

Where the CEO is often the visionary big thinker, usually there's a co-founder, COO, or Customer Support who regularly in touch with the customer and can provide the boots on the ground perspective. This provides healthy contrast to the CEO's visionary ambitions and can uncover new priorities and areas of concern that Jane will investigate further.

During this phase, the technical review is conducted. Discussions with the lead developer(s), and review of documentation, repositories, architecture, and infrastructure will determine the resiliency of the codebase. Discussions with developers will also give a feel for how receptive the company has been towards dealing with issues like tech debt and an understanding for the leadership's discipline when it comes to sticking with a plan vs. constantly changing course. You'll also gain an understanding of the technical proficiency of the development team and their level of enthusiasm around the product.

At this point, Jane will also interview other key employees in other departments to get their perspectives on the past and future direction of the company, and assimilate this information into her understanding of the company. Having done this before, Jane will be able to take the inputs of all these stakeholders and balance the feature and product requests of the CEO with the customer needs and limitations of the customer-centric founder and the tech debt and technical requirements of the developers. This leads Jane to the next step, Roadmapping

Roadmapping: Vision, Mission, Objectives, Strategy

Now that Jane understands the company's background and aspirations, it's time to turn this into a plan (aka. Roadmap) that will inform the rest of Jane's activities and recommendations in the following phases. It would be a mistake to jump straight into defining a roadmap at this point because it is often the case that while early stage startup founders can wax poetic about their vision and aspirations, a focused vision and mission (at least for the next 12-24 months) is usually lacking.

Jane's next step at this phase is to define:

• Vision - Defines what the company wants to achieve
• Mission - Defines how the company will achieve their vision
• Objectives - Typically include business and product objectives and specify what the company aims to achieve in each of these areas
• Strategy - Also defined explicitly for business and product, specifying how the company will achieve the objectives set forth for the business and product

Ultimately, each of these items should roll up to, and support the items above it. Finally, with this defined, Jane can focus on the roadmap, identifying epic-sized items and tying them back to the business and product objectives and strategies. This way the roadmap can stay focused and the reasoning behind each roadmap item can be explained by the objectives and strategies of the company.

Hiring: Finding talented developers

Writing about hiring developers could be the sole subject for an entire blog. Since Jane now knows what the company wants to build, and the company often doesn't have [enough | the right | any] developers at this phase, she must now switch into recruiting and hiring mode and find talented developers that are excited about the product and opportunity.

Hiring for developers is challenging, but not impossible. The goal is not to find the rockstars, ninjas, or 10xers, but to find developers with the right skills, experience, personality, and interest that best matches with your startup's stage,  product, and culture. These are the talented developers for the purposes of our discussion.

Step one involves marketing and selling the unique aspects of the role such as ground-floor engineer, remote / async / four-day-workweeks, or cutting edge, interesting technology to build. It's important to keep in mind that your startup is just one of many thousands that sought after developers can choose from. How you market and differentiate your opportunity from others is extremely important. Posting job descriptions and marketing the positions are typically done by recruiters or HR, but many early stage startups lack this capacity and thus it often falls on the shoulders of the Fractional CTO.

Step two is filtering the applicants for talent. This is where our fCTO, Jane will prove her worth. Being able to identify our definition of talent above, is part art, part experience and involves much more than considering the credentials and experience on a resume. Jane will conduct many phone screens with applicants that look good on paper that will allow her to evaluate them for aspects of experience, personality, and interest, and whether the candidate would be a fit for the company's culture. Candidates that are a good fit are scheduled to meet with the CEO, lead developer, and select key employees.

Hiring for talent takes time and patience. Rushing the process and settling on candidates that don't meet your hiring criteria will result in lost time, productivity, and hard conversations down the road. It can often take a month or more to start seeing talented candidates, and it's often advisable to "always be hiring" as there is latency involved when starting up a hiring campaign.

Up Next

Jane has covered a lot so far in her Fractional CTO engagement with our early stage startup. She has identified the company's needs and laid groundwork for the upcoming phases. In part two of this series, the focus will be on execution and transition. Thanks for reading and stay tuned for the next post.