2.4 Dilemmas: Top salesperson frustrations

In this episode of the Real Sales Manager podcast series 2, we explore complex sales management dilemmas, including handling top salespeople's frustrations, resource allocation during large deals, and managing underpaid employees considering resignation. Our expert panel shares practical insights and strategies to navigate these challenges effectively.

Topics

·      Managing top salespeople's frustrations

·      Resource allocation during large deals

·      Handling employee resignations due to pay

·      Balancing short-term wins with long-term strategy

·      Building trust and consistency in leadership

·      Understanding underlying causes of sales person behavior

·      Effective communication and coaching strategies

Guests

Richard Bounds:

Richard brings more than three decades of sales and leadership expertise across startups, scale-ups, and global enterprises, with experience leading teams of 30+ sellers and driving consistent, high-impact growth. His track record includes doubling turnover at Box-it by transitioning to a cloud-first model, scaling a business from zero to $4M in just 18 months before a successful trade sale. Built a $25M partner channel at Software AG and delivered record results at OpenText as VP EMEA. Today, Richard supports technology companies as a Board Advisor and Fractional Leader, helping organisations build stronger sales functions, implement best practices, and accelerate revenue through structured coaching, advisory, and modern sales approaches

https://www.linkedin.com/in/richardbounds1/

Sophie Steel: 

Sophie is a coach, trainer, and recovering sales manager who now spends her time figuring out what actually makes people perform. She loves mindset, behaviour, and all that good stuff—but mainly she enjoys calling out the gaps between what we say we do… and what’s really going on. She’s an ICF PCC coach, EQ-i qualified, and specialises in brain and behaviour change—working across sales teams and senior leaders to turn insight into actual behaviour change, not just good intentions.

https://www.linkedin.com/in/sophie-steel-72218817/

Special Guest: Phil Loudoun

Phil Loudoun is Head of Sales for the Private Sector at Boxxe - having been with them and CAE who they acquired for over 15 years. He’s been an Account Manager and had various Sales Management positions  before taking on his present position some 18 months ago. He describes himself as A results driven sales leader with a reputation for integrity, loyalty and high performance. He says that he thrives on building strong relationships and collaborative cultures that energise teams, strengthen customer partnerships and deliver exceptional results. 

https://www.linkedin.com/in/philip-loudoun-58284826/

Sound bites

"Let the content dictate the format."

"Think through the consequences of your actions"

"The brain loves certainty."

"We must support our people"

"Money is not the only motivator"

"Treat the issues, not just the symptoms."

"Consistency for a leader is key"

Keywords

sales management, leadership, team dynamics, resource allocation, employee retention, sales strategy