Although I’m the founder of a travel-tech startup, I don’t have a technological background myself. So, I’ve learned the hard way the importance of finding a competent and compatible CTO.
I have also felt, firsthand, how challenging it can be to find such a person. Choosing the wrong CTO caused me to change my engineering team twice, and in the process, I lost two years and $600,000. Not the ideal scenario for any founder.
Eventually, I found a CTO who delivered on every promise. The result? We deployed our back end in only two months. This speed allowed us to develop our search engine, including the platform and client portal, in only 18 months, despite expert predictions that the project would take three to five years. All this took place as the broader travel industry was surrounded by skepticism and uncertainty.
This entire experience reshaped my approach to selecting a CTO and inspired me to share the lessons I learned with other founders. If you’re developing an idea and are not a techy person, following these steps will save you time and money and increase the odds of making your startup dream a reality.
5 Tips to Hire the Right CTO
- Evaluate candidates properly.
- Streamline your sourcing process.
- Verify your CTO’s tech-related track record.
- Get your CTO to stay.
- Set the right milestones and communicate clearly.
1. Evaluate Candidates Properly
One mistake that many founders make is not thoroughly assessing their CTO candidates. The excitement and urgency to bring their coding fantasies to life can overshadow the need for a strategic approach. Choosing a CTO is a long-term commitment, however, and the decision needs to be informed by both quantitative and qualitative assessments. Beyond the technical side, you need to consider the cultural fit. Find someone who aligns with your values and shares the same passion and commitment to the company’s biggest purpose.
If you evaluate your CTO the right way, they might stay with you not only for one venture but for many. Successful examples include Slack, co-founded by CEO Stewart Butterfield and CTO Cal Henderson, and which they sold to Salesforce for $27.7 billion. Their partnership, however, dates way back, when Butterfield first hired Henderson as the CTO — then named Chief Software Architect — for another startup of his, Flickr. They sold this first company to Yahoo! for $35 million.
To vet the proper candidate, I suggest creating a scorecard with five to 10 criteria. These criteria can include value alignment, coding expertise, leadership skills, management capabilities, and product-building experience. The purpose of the scorecard is to have some quantitative fundamentals. If there are various interviewers, everyone can fill out a scorecard and compare ratings.
Also, once you hire a candidate, the scorecard should include a column to rate their performance on the job. The idea here is to weigh the abilities perceived when hiring against the performance delivered by the candidate once on the job. This comparison will make identifying any gaps easier and to promptly detect any aspects that need improvement.
2. Streamline Your Sourcing Process
To increase your odds of connecting with the right CTO, you need to streamline your sourcing process.
Accelerators like Y Combinator and Techstars can connect you to founders or CTOs who have experienced failures but have received positive feedback about their technical abilities. These prospects can be excellent choices. First, their technical capacity is clear. They have a proven track record and have built finished products. Second, they’ve likely learned valuable lessons from their first failures and can be a well of knowledge that can help you navigate the perilous times that every startup will inevitably face.
In fact, the HR tech startup Rippling actively hires failed founders because they believe that “failed ventures can have silver linings: they build skills that some companies actively seek out,” as Neha Sharma, Rippling’s head of people, told Insider.
Other ways to attract the right candidates include tapping into your network. If you have no connections in the field, join entrepreneurial communities yourself. Lots of cities now have interest groups that form around startups. For example, Startup Grind is present in more than 125 countries, and its events are a great place to connect with other entrepreneurs, investors, developers, and other tech professionals. And since we’re discussing failures, Fuckup Nights is an enormous community where entrepreneurs from all over the world take the stage to talk about their mistakes. Their events happen in over 200 cities across 65 countries, so you can likely find one close to you.
3. Verify Your CTO’s Tech-Related Track Record
Since you’re not the technical person on the team, I recommend that you engage two advisors to support you in the process of verifying your CTO’s technical skills. One of these advisors will conduct technical interviews, while the other one will gauge the product-related aspects of the candidates.
The goal here is to ensure that your CTO is fully competent and can develop the product that you’re looking for. Having advisors assist you in the process increases your odds of having someone on your team who has the technological skills and experience to bring your vision to life. This acumen will be a great asset not only for this startup but for your overall entrepreneurial journey.
A success story in this arena is Bobby Murphy, Snapchat’s CTO. Murphy was hired by co-founder Evan Spiegel, who first contacted Murphy to build another startup called Future Freshman. Though that platform failed, Murphy’s technical abilities were top-notch. So, he stayed on board for the next venture, which eventually made all of the co-founders billionaires.
4. Get Your CTO to Stay
People who are well-versed in technical skills are in high demand, and they’re likely to secure a high-paying job almost anywhere. So, even if the value alignment is there, the compensation package is essential.
Expect equity to be a part of the conversation. The number of shares you should offer the CTO largely varies depending on the startup’s stage. Regardless of the amount of equity you offer, however, to make this arrangement beneficial for both sides, I recommend implementing a vesting option for the CTO. This setup will increase their commitment to the company.
Dr. Noam Wasserman, a professor at Harvard Business School, came to the conclusion that founders who are willing to share more equity with co-founders, investors, and early employees end up building more valuable companies. This, in turn, increases the value of the founder’s equity and creates a committed, motivated core team that is willing to give its all to help the company grow.
5. Set the Right Milestones and Communicate Clearly
Your job is not over once you’ve hired the right CTO. Now, both of you need to collaborate on creating the right roadmap to reach the company’s goals. To do this, define the right KPIs and metrics that will be used to measure progress and agree on the relevant milestones that you need to reach as a team. These need to be outlined based on what your product requires. A SMART framework can ensure that these KPIs are well-defined and that they seem attainable. One common KPI for developers is, at an early stage, the time-to-market (TTM). Once the product launches, other KPIs are tech debt, system uptime, and incident response time.
A common problem that founders face is that they speak a totally different language from that of their CTOs or technical co-founders. To attain success, however, you must bridge this divide. If there is no proper communication between you and your CTO, failure is guaranteed. Proper communication involves managing expectations, which a Pretius report highlights as the toughest challenge in the IT industry today.
To address this, I recommend that you’re open and transparent and also that you’re not afraid to ask questions. Sometimes, technical people can use uncommon terms. Ask for clarification, and don’t be afraid of looking silly. This will guarantee that you’re both on the same page. Ongoing communication is required, however, as this will help you have full visibility of where the project is at all times and if there’s anything you can do to help.
Get the Right CTO the First Time
The role of the CTO in a fledgling venture is extremely important and often underestimated. And, as I learned the hard way, choosing the right CTO isn’t easy.
By following the steps above and giving your CTO selection process the proper importance, however, you’ll make it likelier that you find the right candidate. This means you get one that will complement your strengths as a non-tech founder and that propels your startup idea and increases the odds of making it a reality.
By having the right technical partner, you can focus on those areas that you know best. Together, you can elevate your product to new heights.
