Outsider Insights | The Backup Plan You Don't Have Is Already Costing You

Outsider Insights

Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.

The Unseen Cost of Team Turnover and How to Prepare for it

A Vacancy in Your Org Chart Will Cost Money, Not Save It

If losing a key position saves your organization money then you hired the wrong person. A wide variety of reasons can lead to the departure of a talented leader or team member. The loss of their expertise can slow business and stifle growth.

Business Doesn't Wait While You Fill a Role

A CEO called us recently because his VP of Sales had just resigned. He urgently needed someone to carry the revenue torch and manage his sales team.

Another client suddenly lost multiple members of its marketing team. Marketing programs couldn’t just stop while they recruited replacements. They needed to keep the work moving.

We hear versions of this all the time.

Sometimes a leader resigns unexpectedly. Sometimes a CEO knows a change needs to be made but hesitates because there’s nobody ready to step in. Sometimes the leadership is fine, but the team is missing critical people or capabilities.

Different causes. Same problem.

The business still has to run, but it no longer has the team it needs to do it.

Hiring, staffing and retention remain among the challenges CEOs talk about most. The Vistage CEO Confidence Index has highlighted talent management as the #1 concern for mid-market CEOs. And there’s good reason: the best growth strategy in the world doesn’t matter if you don’t have the people to execute it.

A Vacated Role in Your Company Costs More Than You Think

Most mid-sized businesses run lean. When an important commercial leadership role opens up, there often isn’t a qualified successor waiting in the wings.

So one of a few things happens. The team goes without a clear leader. Someone internally steps up before they’re really ready. Or the CEO takes over - which often means adding two jobs to an already-full plate: running the function and finding its next leader.

A team-level gap creates a similar problem. An important part of the commercial plan may go undone, or it gets handed to people who lack the expertise, capacity or time to do it well.

No matter where the gap lies, we see the same results. Priorities get deferred. Decisions slow down. Momentum stalls. People get frustrated. And over time, more good people walk out the door.

The toll is easy to underestimate. Every week without the right leadership or resources is a week when the commercial organization is operating at less than full strength. Eventually, that shows up in your pipeline, revenue, or customer experience.

CEOs See the Problem Coming, but Don't Have a Plan B

Some gaps appear overnight. Others develop slowly.

Maybe your sales leader was right for the company two years ago, but the business has outgrown them. Maybe you’ve known for months that your marketing team lacks an important demand-generation or Rev Ops capability. Or maybe someone simply isn’t working out.

Often, CEOs see the issue long before they act.

The reason is understandable: making a change can feel riskier than just living with the problem. Replacing someone creates a hole. Adding capabilities costs money. An executive search takes time.

But waiting creates its own cost. Opportunities get missed. Frustration builds. Strong people leave. Progress stalls.

And, eventually, that builds until the problem becomes urgent.

And that’s when another risk appears: rushing the solution. A search can take months, and urgency can lead to a compromise hire you wouldn’t otherwise make.

Waiting isn’t a good answer. Rushing isn’t either. So what should you do?

Five Options to Address a Gap in Your Commercial Team

There are several ways to address a commercial leadership or team gap.

1. Permanent Hire – Often the right long-term answer, but senior sales and marketing searches take time. The business still needs leadership while the search happens.
2. Internal Promotion – A great option when there's a genuinely ready successor, but in lean mid-market organizations, that's often not the case.
3. Reassign to Another Leader – This can work temporarily. But if the role is critical to your business, turning it into someone else's side responsibility may mean it no longer gets the focus it deserves.
4. Fractional or Interim Executive – An experienced CMO or CSO can step in quickly, stabilize the team, keep priorities moving, and give the CEO time to make the right long-term decision. And, that leader can also bring in marketing, sales, RevOps or other execution resources to replace or add missing capabilities – which is particularly useful when the need is temporary, specialized, or urgent.
5. Fractional or Interim Specialists, Managers, and Directors - Agency prices are astronomical and, honestly, the individuals managing your account are entry-level or early in their careers. Embedded fractional support to shape and execute strategy will help maintain team momentum, deploy quicker than a new hire and are more cost-effective than an agency.

Which one is the right answer? That depends on the situation, and it may be a combination.

MUST-READ: When to Hire a Fractional CMO vs Full-Time CMO

That’s because you’re really solving two problems: what the business needs right now versus what it needs long term. A bridge solution lets you solve today’s problem without rushing tomorrow’s organization.

Be Prepared with a Commercial Talent Backup Plan

You won’t prevent every gap.

People will resign. Someone who was right for a role may no longer be. Your strategy will change, creating needs you don’t have today.

Few businesses can keep a full bench of executives and specialists waiting in the wings.

What is a commercial talent backup plan? A commercial talent backup plan is a proactive strategy that identifies which revenue-critical roles and capabilities must remain covered, and outlines how the business will maintain continuity—through internal resources, fractional executives, or interim hires—when a gap occurs.

Commercial Talent Backup Plan Checklist

Start by asking yourself:

What absolutely must keep working to drive our commercial priorities?

What people or capabilities are required to keep that moving?

If we lost one of those people or capabilities, who could step in fast?

Where do we need to buy time to find the perfect fit versus filling a role fast?

Knowing the answers helps you react quickly instead of turning the CEO into the emergency sales leader, marketing manager and recruiter. And the business keeps moving while you buy yourself time to find the right long-term solution.

The question isn't whether you'll eventually have a gap somewhere in your organization.

It's whether, when it happens, you'll know what to do next.

Key Terms:

• Fractional Executive: A part-time, experienced leader who works with your company on a flexible basis, typically a few days per week or month.
• Interim Executive: A temporary full-time leader who fills a role during a transition period, often while a permanent search is underway.
• RevOps (Revenue Operations): A function that aligns sales, marketing, and customer success operations to drive efficient revenue growth.

Frequently Asked Questions

How do you communicate a leadership gap to your commercial team without triggering further turnover?

Transparency and speed matter more than most CEOs expect. Teams already know something is wrong — silence usually makes it worse. Acknowledge the change quickly, name a clear point of contact for day-to-day decisions, and share a timeline for what comes next, even if that timeline is approximate. If a fractional or interim leader is stepping in, introduce them with authority and context. Uncertainty is what prompts good people to update their resumes. A credible interim plan reduces that uncertainty.

How do you evaluate whether an internal candidate is genuinely ready to step into a leadership role?

The honest test is whether you would be comfortable with them in the role permanently, not just temporarily. Consider whether they have managed at the scope the role requires, whether they have credibility with the team and key stakeholders, and whether stepping up would ask them to do things that are genuinely new to them versus merely unfamiliar. When the answer is "not quite," a fractional executive can work alongside the internal candidate, providing senior judgment while that person develops. That arrangement is often more effective than placing someone in a role before they are ready and expecting them to grow into it under pressure.

How do you know when it is time to move from a fractional or interim solution to a permanent hire?

A few signals indicate the timing is right: your strategy is stable enough to define what the role needs to accomplish long-term, you have a clear profile of the person you are looking for, and the fractional leader has stabilized the team and restored visible momentum. If the engagement is still surfacing new organizational problems, a permanent hire may arrive before the role is well-defined — which increases the risk of another mismatch. The fractional leader can often help write the permanent job description and participate in the hiring process, which makes for a cleaner handoff.

What should you look for in a fractional CMO or CSO to make sure they are the right fit?

Industry familiarity helps but is rarely the most important factor. More important is whether the person has operated at the stage of growth your business is in. A fractional leader whose experience is primarily with large enterprises may struggle to move quickly in a lean mid-market environment. Look for someone who can diagnose fast, communicate directly with a CEO, and prioritize rather than try to address everything at once. References from companies at a similar scale and stage are more telling than brand-name credentials.