3 Go-To Tips for Hiring Top Execs as Your Company Grows 

By Olga Bortnikova

As a company grows, there’s a point where founders must start delegating some responsibilities to their team to scale the company further. This might involve hiring a CEO, CTO, or other executives. 

The process is undeniably challenging. Especially if the founder lacks expertise in more technical areas, it is difficult to validate a candidate’s competencies and skills.  

Here are three tips that, in my experience, have helped me hire a leadership team that has accelerated our expansion and bolstered our impact.

1. Tap into insider wisdom  

Usually, the hiring process comes with more questions than answers. To solve this issue, I’ve streamlined our approach.  

Let’s say we’re looking for a marketing director. First, I outline our marketing goals for next year, and identify our most pressing marketing-related problems. 

With the answers, I scout around, and reach out to someone who, as a marketing director, has successfully solved these concerns. The intention is to have a call with them, explain our goals and issues, and ask some specific questions:   

• What key experience should I seek in my future marketing director?  
• What test assignment should I give them? 
• Does my offer meet the expectations of the candidate I am looking for?  

Learning in detail how a marketing director would answer these will provide a rough idea of what the company’s future marketing director’s CV should look like.  

If reading this you think no one will want to talk to you, you’re wrong. Even the marketing director of a large organization will be interested in talking to the founder of a small company because of the level difference.  

2. Use AI to help yourself draft a creative job description  

The next step is to create the job description for the position. AI can be of paramount assistance, but the key lies in being as specific as possible when prompting.   

To do this, I compile a list of KPIs that my future marketing director will need to meet, and ask AI to generate a job opening considering them. Here is the example of the prompt: “using the CMO KPIs, create a job description for CMO, outlining the key focuses and expectations from the CEO. This should be done in a simple and straightforward language. The structure must include: About the Marketing Team, About the Role, Responsibilities, Requirements, About Tripsider.” And here’s what we have as the role description: 

“In this role, you will be a key player in promoting and scaling a unique type of travel – custom tours by Tripsider. You will directly impact the company’s growth by developing and optimizing processes for attracting, activating, and retaining customers through carefully crafted marketing and communication campaigns. We’re looking for someone who not only understands data but also knows how to apply it to create effective strategies, providing our users with a personal and unforgettable experience. Join our dynamic and rapidly growing team, contribute to its success, and leave your mark on the history of Tripsider.” 

To clarify the posting even further, you can ask what the top 3 tasks for the new marketing director are. While the answer may seem apparent, it’s essential to clarify them to ensure expectations are aligned.  

Surprisingly, the chatbot adeptly selects wording that resonates well with professionals in the field. We’ve already conducted such an experiment, and even financial managers appreciated it.  

3. Involve industry professionals in the interview process  

As the leader of the company, you can always gauge a candidate’s soft skills and assess whether their personality can be a good cultural fit while conducting an interview.  

However, evaluating the technical skills of a prospective CTO is a different story.  

For this, I invite an industry professional to the interview. Ideally, this will be the same person you consulted with for step 1, as they will already have a familiarity with your goals. 

There’s a further benefit to this — industry professionals will often recommend candidates for the positions you’re hiring for.  

We’ve often hired cool specialists who hadn’t announced publicly they were looking for a job, but we knew about it through our internal communication channels.  

Final thoughts 

Hiring the right C-level executives is not easy. However, it is worthwhile to invest in the initial recruitment process, as it paves the way for the company’s future.  

By tapping into insider wisdom, leveraging AI to draft a creative job description, and involving industry professionals in the interview process, you can increase the odds of finding the right talent to supercharge your company’s growth.

About the Author

Olga Bortnikova is a seasoned entrepreneur, travel expert, and the co-founder of travel tech startup Tripsider. Under her leadership, the companies have grown into booming platforms with over $30M GMV and more than 500,000 monthly users. Olga is a certified mentor at UN Women and holds an ICF Certified Coach designation.