Hiring for Your C-Suite: A Framework for Finding the Right Talent to Steer the Ship

Over the past two years, we’ve run three searches for CEOs, and, as with all parts of our methodology, we’ve spent a good amount of time reflecting on how to make the process even better next time. 

In this article we share what’s at stake, what we’ve learned, and our (current) process for landing our next great hire.

When to hire, and what’s at stake

At 19days we hire CEOs at a strategic moment in the venture creation process. Before hiring, we’ve completed discovery, problem definition, concept development, concept validation, prototyping, and have validated the prototype. At this point, the product is in development; we may have hired some key people into the venture (e.g., engineers, product managers, and SMEs); and it’s time to bring in a CEO to execute on the established vision.

We hire specifically at this moment because, although there is a vision-defined by stakeholders and a team running after clear objectives, success depends on having an experienced person dedicated to championing the problem that we are solving and the established vision, while also being able to dedicate all of their time to creating momentum, overcoming obstacles, and aligning a team.

Needless to say, we’re looking for a specific type of person. A great hire can be the spark plug to a venture; the wrong hire can derail what was previously a promising business with early momentum. The ideal candidate has some level of domain expertise in our selected vertical, has worked in a SaaS environment, and has the intrinsic motivation and determination needed to lead a very early-stage venture.

Also needless to say, it’s time consuming and expensive to find this person. The 19days team spends $6,000-$8,000 and between 400-500 hours to hire a CEO. Naturally, we continue to look for ways to drive both of these metrics down while elevating the overall level of talent pouring into our hiring funnel.

Along the way, we’ve established a process with proven success, which we’ll outline here for you.

1. Plan 

It sounds simple, but we can’t overstate the importance of taking time to plan both the hiring process and squarely align on the requirements for the role and the qualities of an ideal candidate.

Taking the time to define these components early on, saves you from wasting time later in the process as a result of a poorly written job description, uninformed targeting for hiring campaigns, ill-prepared interview questions, and ineffective decision-making criteria.

Our planning phase includes: 

  • Operator scoping - This is where we zoom out and look at the venture as a whole and where the CEO role will fit within it. In other words, we ask ourselves, “what experience or skill gap in the organization chart will our ideal CEO fill?”
    In our SaaS ventures, we tend to look for someone with product, operational, or sales and marketing experience, or some combination of the three, depending on the other areas of expertise represented in our lineup. Defining the type of leader we’re looking for allows us to hone in on our anchoring statement. This is a line that guides our team throughout the entire hiring process, and it can be as simple as, “we need an operator and organizational engineer.”
  • Role discovery - Once we know where our ideal CEO will fit, we start zooming in on what their role will look like. We do this by creating a role profile that outlines how they will apply the strengths defined in the operator scoping stage to day-to-day responsibilities. We also use Gitwit’s Innovator Capabilities methodology to cut through the noise of varied perspectives on which skills are most essential and surface precisely which type of innovator we’re looking for. Spending the time to align around a clear vision for the role is crucial input for the next steps.
  • Job Description Story Session - With the CEO role defined and shaped at the organizational and individual level, we kick off the creative brainstorming process for our job ad. Our goal here is not just to stand out from the job ad crowd, but to speak directly to our ideal candidates’ wants and needs. To identify what details will resonate, we start by asking ourselves questions about the role:

    • What is the CEO’s mission? 
    • What problem will they solve? 
    • What pain points are our ideal candidates struggling within their current role? 
    • How can we make those better here?

    It’s important to note that this is not an elimination phase. The goal of our job ads is to act as a magnet, attracting as many people as possible and trusting that paring down will come later. We find that writing our ads in a voice that’s genuinely ours and doesn’t oversell attracts the most like-minded candidates.
  • Confidential Profile Development - The Confidential Profile—a hiring process component we were exposed to thanks to Bryce Murray of Talent Acquisition Group—synthesizes all of our learnings, insights, plans, and vision into a clean, digestible view for potential candidates’ review. This piece tends to wow because we bare it all (usually under NDA). 

    We hear from a large majority of our candidates that they haven’t seen this type of information disclosed in a hiring process before. Not only does this legitimize who we are and the work we do at our venture studio, it provides candidates with a transparent, holistic view of the venture and the role they would play in running it. After all, at this level, top candidates will be evaluating us as much as we’re evaluating them.

Each part of the planning process is designed to build excitement among candidates as they move through each step. The confidential profile is one of the critical moments that hooks candidates and demonstrates our commitment to treating each person with care as we make progress toward finding the right fit.

2. Recruiting and Reviewing 

Next we establish a process for both going out and sourcing great candidates, as well as swiftly reviewing candidates who apply.  

During this process we are specifically looking for qualifications that check all of the boxes of our CEO criteria as well as ‘glimmers of greatness’ — indicators that this is a special person, who might be uniquely suited to take our venture to the next level. Glimmers of greatness can be specific relevant experience, a particularly strong point of view, or even a personality trait that we think could be powerful in rallying the team or driving early sales or partnerships.

Our recruiting process includes: 

  • Posting the job - We kick off our recruiting process by sharing our job ads on our LinkedIn, on our website, and with our network. We tend to avoid job boards and the noise—read: spam postings and candidates—that comes with them.

    A quick tip: The best day to post a job ad is Monday when people are coming back from the weekend to a job that’s leaving something to be desired. While many people may have ‘look for jobs’ on their weekend to-do list, they’re more likely to unplug than see your job ad in a Friday job search. 
  • Sourcing - The amount of time needed for candidate sourcing is dependent on the performance of your job ads. The more attractive your job ad is, the less time you have to spend reaching out to potential candidates. The job ad for our last CEO role, for example, was earning us hundreds of high-quality inbound leads, allowing us to dedicate more time to reviewing applicants.
  • Reviewing - We start looking for ‘glimmers of greatness’ by reviewing candidates’ personal summaries, LinkedIn profiles, and resumes, and then we begin making calls. After a couple of calls with 19days’ talent acquisition manager and managing partner, applicants move to an experience interview with two of the 19days founders. If the experience interviews reveal glimmers of greatness, we also ask applicants to complete an assignment and Gitwit’s innovator capabilities assessment to further develop our understanding of their skills.

As we review, we make it our mission to reply to all applicants out of respect for everyone who has taken the time and put forth the effort to reach out and apply. Throughout each step in the vetting process, we aim for a communication cadence of candidate updates every 10 days, whether those updates are good, bad, or no news yet.

3. The Tulsa Visit 

Once we have selected a few high-potential candidates, a key part of our process is bringing these people to Tulsa to meet the 19days team, learn about how we operate, experience the work environment, and discuss in more depth the venture, our goals and theirs, and their desire for the position.

We have found that this dedicated in-person time with candidates is the best way for our team and our top candidates to learn how it actually feels to work together. The in-office visit is another way to sell each other on our fit and validate that this is a real, promising opportunity beyond the words exchanged on a phone call, polished resume, or attention-grabbing job ad.

We typically block off a week to bring candidates in, one day after the other, and then a final decision-making day after the last candidate leaves.  

Sample visit schedule:

At the conclusion of our last search, four out of four candidates said it was the best, most thorough process they’d ever been through, and that it made them exponentially more excited for the opportunity.

4. Making the Decision

Ideally, at this point in the process, you have to make a really hard decision between several great candidates. If the process has been successful, this becomes the most difficult step.

We’ve designed a decision-making process that relies on both objective assessments of the person, as well as the personal feelings and opinions of stakeholders that should not be overlooked.

As we review our top candidates, we reflect on each step in their vetting process, comparing our notes with our original anchoring statement about the ideal candidate we said we were looking for at the outset. We ask ourselves which candidates delivered on the aspects of our anchoring statement. Knowing what we know about our strongest candidates, we also reassess our anchoring statement to ensure it still feels like the right goal. This creates space to voice any new, unexpected insights into the role and/or ideal candidate that may have been gathered throughout the vetting process.

Overall, we dive into our process for hiring a CEO with a highly objective mindset. Our planning and initial vetting steps, while still human-centered, feel focused, structured, and fact-forward. However, as we reach our introductory calls, interviews, and in-office visits, we begin to pay more attention to our feelings and observations—our ‘gut instinct.’ This reverses the typical process of calling candidates based on a gut feeling and then making tough decisions based solely on what’s on paper. It helps us make better decisions more efficiently and sets our team and new hires up well to hit the ground running in the next phase of our ventures.

5. The Retro

Finally, we have found that just as important as the hiring process is a retrospective meeting. Following the CEO’s hire, all of the 19days team members involved in the hiring process meet to assess what worked well, what didn't, and what we’d like to try the next time we hire.

Capturing these learnings, ideas, and feelings while they are still fresh is key to understanding the real meanings behind them and intentionally incorporating them into the planning phase of the next process. We like to follow the 4L structure for retrospectives, asking each person what they loved, longed for, loathed, and learned. We also review time spent and budget of the entire hiring process.

There is the idea that with hiring, and venture, you need to get lucky. While the others wait for luck, why not grind through a few cycles to try and refine a process that can consistently deliver strong results?