Securing the Right Sales Leadership: Challenges, Characteristics and Recommendations
By Neil Morrison
October 23, 2025
Finding the right sales leader is one of the toughest tasks for any company.
Why's that?
Because great sales leadership can’t just focus on outcomes – it’s about developing, coaching and inspiring a high-performing team in a constantly evolving environment.
Here are some of the top challenges organizations face when trying to find the right fit:
Highly competitive/smaller talent pool:
The ideal sales leader is both a successful salesperson and an effective coach – a rare combination. A common misconception is that top salespeople naturally make great sales leaders, but the skill sets required are very different.
Limited knowledge of modern selling:
The world of sales has evolved dramatically. Buyers are more sophisticated, and selling techniques must continuously adapt to keep up. As a result, many hiring managers aren't fully attuned to what today's top sales leaders need to succeed.
Undervaluing the role of sales leadership:
Companies tend to underestimate the impact sales leaders can have. The best can double or even triple sales performance - and their compensation should reflect that level of influence.
No clear designations:
Sales isn't a regulated profession with a governing body and protected titles like accounting or law. There are no standard designations (like an MBA or CPA) to benchmark against, making it more difficult to identify the right candidate.
The number one challenge? Finding a sales leader who can both sell and coach.
Many selling styles don't lend themselves to being good leaders (e.g. a lone wolf salesperson) and there are different qualities that make someone a good salesperson vs. a good leader.
So what does distinguish a strong sales leader?
A great coach:
They see their primary role as helping people succeed through empowerment and coaching.
High emotional intelligence:
A successful sales leader knows how to read people and can adapt their coaching style to individual needs.
Motivational and inspiring:
Sales is a rejection-heavy environment; A good leader would be able to rally the team and boost morale when times are tough.
The voice of the team and market:
Sales leaders act as a critical bridge between the sales team, clients, the market and the broader organization. They bring insights about market dynamics, competitive offerings, and shifting customer expectations back to leadership.
A positive disruptor:
This characteristic is particularly important for a modern sales leader who needs to guide and push people in the right direction and speak up when something needs to change.
Choosing the wrong sales leader can have serious consequences. It can lead to a demoralized sales team, high employee turnover, missed targets, loss of momentum and eroded customer relationships. It can also have a ripple effect across different departments as sales results are a key indicator of company success. Poor sales results can lead to a company-wide negative outlook and job security concerns.
To get ahead of this problem, partnering with a specialized executive search firm can add tremendous value.
An experienced executive search partner brings access to 'passive candidates' (those not actively looking for new roles), provides market and compensation insights, understands the evolving attributes of modern sales leadership and has the resources and processes to run a thorough, effective search.
Our recommendations for CEOs hiring their next sales leader:
Look for a proven track record of high performance in the sales industry.
Assess their coaching ability, emotional intelligence and self-awareness.
Seek strategic thinking and a growth mindset.
Target candidates who empower their teams rather than micromanage.
Find someone who isn’t afraid to challenge your thinking - and who pushes their team outside their comfort zone.
Find the right sales leader, and everything else in the business will start to move in the right direction.
About the Author, Neil Morrison:
Neil Morrison, Partner, Executive Search and Leadership Consulting, MondouxRollins Partners Inc.
Neil Morrison is a senior leader and trusted advisor, focused on helping clients drive growth through exceptional leadership talent recruitment and development. As a partner in our executive search and human capital advisory practice, Neil helps clients find solutions to leadership talent challenges. Whether it's a search for a new executive leadership position, or a leadership team assessment, he works strategically and collaboratively with clients and candidates to ensure outcomes meet expectations. With over 30 years of experience, Neil offers deep expertise in sales and distribution leadership in the insurance industry, including B2B and wholesale business development and client management. His career began as a top-performing sales representative for 15 years, after which he transitioned into leadership roles focused on developing and inspiring high-performing teams. He shifted from being on the front lines to guiding and leading others to succeed - evolving from a player to a coach. Neil holds a Bachelor of Commerce and an MBA from the University of Windsor, as well as the CEBS (Certified Employee Benefit Specialist) designation, underscoring his commitment to professional excellence.
About MondouxRollins Partners Inc.:
MondouxRollins Partners Inc., is an executive search and human capital advisory firm. We are a group of specialists, equipped with decades of experience providing talent solutions for private companies. We are risk-mitigators, trusted advisors and relationship-builders, and we are your one-stop-shop through the entire talent lifecycle - for your team, or for your board. We are also the founders of the Canada’s Best Private Boards program, a first-of-its kind national and annual awards program that recognizes the impact of governance on the performance of private companies.
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