Navigating the Sales Talent Gap: Strategies for Developing and Replacing High-Performing Salespeople

May 11, 2023

IBA, as the premier business brokerage firm in the Pacific Northwest, is firmly established as a respected professional service firm in the legal, accounting, banking, mergers & acquisitions, real estate, and financial planning communities.  Periodically, we will post guest blogs from professionals with knowledge to share for the good of owners of privately held companies & family owned businesses. The following blog article has been provided by Jason Cutter of the Cutter Consulting Group (

Navigating the Sales Talent Gap: Strategies for Developing and Replacing High-Performing Salespeople

Sales organizations must not only fill the gaps left by retiring sales veterans but also develop new salespeople. As a sales leader and consultant, I’ve seen it all – the highs of hiring a superstar salesperson who crushes their targets, the lows of losing a veteran who took years to build relationships with customers, and the panic of trying to fill an urgent talent gap (and all the slumps that happen along the way). Developing and replacing high-performing salespeople is critical to building a strong, sustainable sales team. I want to share the challenges of developing and replacing sales talent, along with strategies for addressing them.

Proactive versus Reactive

Leaders know that being proactive with talent management is crucial to building a strong sales team. But let’s be real; most of the time we live in a land of “hope” – that our experienced, high performing salespeople will never not perform and will never leave us. When an unexpected talent gap opens, we end up in reaction mode. We need to have a plan in place for when the inevitable happens.

Now, some might say that the best defense is a good offense, and they’re not wrong. But, let’s be honest, in sales, sometimes you just need to react. When the star salesperson who has been bringing in a significant portion of the revenue for the company decides to up and retire, it’s not like you can just go and replace them overnight.

The key is to invest in constant, proactive talent management, including identifying high-potential salespeople and providing training and development opportunities. However, reactive talent management is also important, as unexpected departures can create urgent talent gaps.

Loss of Talent, Network, Relationship Building

As Baby Boomers retire from the sales force, companies are facing a significant talent gap. Retiring sales veterans take with them years of knowledge, experience, and relationships. To address this talent gap, organizations should focus on knowledge transfer and relationship building.

Effective knowledge transfer involves capturing the expertise and knowledge of retiring sales veterans and transferring it to new salespeople. Relationship building involves leveraging the network of retiring sales veterans to establish relationships with new customers. A diverse and multigenerational sales team can also help address the loss of talent due to retirement.

Customers Still Want High Touch

One thing that hasn’t changed is that customers still want a high touch salesperson with the ability to build rapport and maintain long-term relationships. They want someone who they can trust and is looking out for their best interests. And, let’s face it, building relationships takes time.

That’s why it’s so important to have a strong team of salespeople who are dedicated to building relationships with customers. You want to invest in your salespeople and give them the tools they need to build trust and rapport with your customers. And you need to make sure that your salespeople are motivated to do so.

The challenge comes with new salespeople, who do not have the experience of building relationships with prospects and customers. They tend to be more short term, transactional focused, looking for the most efficient way(s) to reach out and close deals with less of the messy people part.

Developing New Salespeople

Let’s face it – no one is born a sales superstar. Developing new salespeople is crucial to building a strong sales team. But it’s not just about training and development programs. New salespeople also need to learn from experienced salespeople and be mentored by them. And let’s be real, experienced salespeople are busy closing deals and building relationships, so finding time to mentor newbies can be a challenge.

Unfortunately, companies get complacent with their experienced salespeople and forget or ignore what is involved with getting a new sales hire up to a profitable level of performance.  The best ways to develop a new salesperson is with a balance of curated, documented training (videos, documents, quizzes, courses – to ensure everyone learns the same thing), plus shadowing seasoned reps. That is, if they haven’t left already or mentally checked out.

We’ve found that shadowing is a great way for new salespeople to learn from the best while also building relationships with customers. But be careful with shadowing. It can work well but you have no control over what they will say and share with your new person – they could potentially transfer their attitude/mindset, feelings about the company/industry/clients, techniques, and behaviors that you don’t like or want perpetuated with others.

“How do I plug and replace?”

Replacing high-producing veterans can be challenging. These experienced salespeople have established relationships with customers and have a deep understanding of the company’s products and services. However, it is crucial to identify and nurture potential successors to ensure a smooth transition when experienced salespeople retire.

Effective succession planning involves identifying potential successors and investing in their training and development. Organizations can also leverage the knowledge and expertise of experienced salespeople to mentor potential successors. A well-executed transition plan ensures that customer relationships are maintained, and the organization continues to grow.

And, let’s be honest, if we’re going to ask experienced salespeople to mentor potential successors, we need to make it worth their while. Incentives, like bonuses, can help motivate experienced salespeople to take on the responsibility of mentoring.

Ah, the panic of trying to fill an urgent talent gap. It’s like trying to put out a fire while simultaneously playing whack-a-mole. The key is to be prepared. Have a plan in place for when a high-performing salesperson leaves unexpectedly. This plan should include short-term and long-term strategies.

Short-term strategies can include hiring contract salespeople, reallocating sales resources, or outsourcing sales functions. These strategies can help fill the talent gap quickly while also giving you time to develop a long-term plan.

Long-term strategies should focus on developing the next generation of sales superstars. This can include investing in training and development programs, identifying high-potential salespeople, and providing them with opportunities to grow and develop. Remember, a little bit of planning can go a long way when it comes to plugging and replacing.


Developing and replacing high-performing salespeople is essential to building a strong, sustainable sales team. Sales organizations must balance proactive and reactive approaches to your team’s development. Ideally, to build a scalable sales operation it must be less about filling the team with superstars and more about systems, processes, and a team that can get great results without having to be truly amazing.

No sports team has ever created a dynasty by filling the roster with only superstars – they also had roll players, people contributing from the bench, and a system that supported it all (coaches, trainers, playbooks, technology, etc.).

The same holds true for sales teams. The era of relying on your salespeople to produce superstar results is over. The generation that could pull that off is retiring, and the buyers have changed. Make sure you are ready for the new era of building scalable sales operations.

If you have questions relating to the content of this article or finding ways to help your sales team improve their effectiveness, Jason Cutter would welcome the opportunity to answer them.  Mr. Cutter can be reached at (206) 234-1848 and

IBA, the Pacific Northwest’s premier business brokerage firm since 1975, is available as an information resource to the media, business brokerage, mergers & acquisitions, real estate, accounting, legal, and financial planning communities on subjects relevant to the purchase & sale of privately held companies and family-owned businesses.  IBA is recognized as one of the best business brokerage firms in the nation based on its long track record of successfully negotiating “win-win” business sale transactions in environments of full disclosure employing “best practices”.