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 Backup Plan You Don't Have Is Already Costing You

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.

An Empty Seat 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.

Often, CEOs Saw the Problem Coming

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?

Options to Address a Gap in Your Commercial Team

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

• Make a 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.

• Promote from within.

  A great option when there’s a genuinely ready successor, but in lean mid-market organizations, that’s often not the case.

• Put the function under 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.

• Bring in fractional or interim resources.

  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.

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

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.

Have the Answer Before You Need It

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.

But you can know what you’ll do when a gap opens. 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.

Frequently Asked Questions

• What should a CEO do when a key sales or marketing leader suddenly leaves?

  Often, it helps to separate the immediate need from the permanent hiring decision. Identify what needs to keep moving and who can provide leadership now. You’ll buy the time to begin a longer-term search without forcing yourself to make a rushed hire.

• When does fractional leadership make sense?
  Fractional or interim leadership can make sense when you need experienced leadership quickly, don’t yet know what the permanent organization should look like, or want to maintain momentum while conducting a thorough executive search.

• Can fractional resources help with team-level gaps too?
  Yes. A fractional resource can provide experienced marketing, sales, RevOps or other execution resources to fill specific capability or capacity gaps quickly.
• Why not just hire a full-time replacement rather than bringing in a fractional executive or team member?
  While a permanent hire may be the right long-term answer, recruiting can take months, and operating without the right leadership during that period can be costly. An interim or executive team member can fill the immediate gap to keep your commercial programs moving, give you time to find the right full-time hire, and even help you determine what to look for in your new hire.
• What should be included in a commercial talent backup plan?
  At a minimum, know which roles are critical, what work absolutely must continue if one becomes vacant, who could step in temporarily (either internal or external resources).