Why SaaS Leaders Need to Start Coaching Selling Skills

Coaching Selling Skills

Why SaaS Leaders Need to Start Coaching Selling Skills

SaaS sales leaders struggle to balance deal-focused coaching and skill development among sales teams. I want to explore why SaaS sales leaders prioritize deal coaching over skill coaching and provide insights on how they can more effectively develop the selling skills crucial for winning deals and creating sustainable growth.

The Emphasis on Deal Coaching

In the fast-paced environment of SaaS sales, where monthly and quarterly targets dominate strategic thinking, sales leaders often focus on immediate opportunities to close deals. This approach, termed “deal coaching,” involves leaders working closely with sales representatives on specific opportunities in the pipeline, guiding them on strategies to advance these deals toward closure.

Three Reasons for this Focus:

  1. Immediate Revenue Impact: Deal coaching directly influences short-term revenue, making it attractive for leaders under pressure to meet their quotas. By focusing on closing deals in the pipeline, leaders aim to achieve immediate financial results, which are tied to their performance evaluations and compensation structures.
  2. Visibility and Accountability: In many SaaS companies, there is a high level of accountability for achieving sales targets. Deal coaching provides a transparent framework for sales leaders to demonstrate their involvement and impact on key deals, offering a direct line of sight between leadership activities and sales outcomes.
  3. Complex Sales Processes: SaaS products often involve complex sales cycles with multiple stakeholders. Sales leaders feel that by intervening directly in deal dynamics, they can better navigate these complexities and tailor the sales approach to specific client needs and scenarios.


They Neglect to Focus on Coaching Selling Skills

While deal coaching addresses immediate sales challenges, it often comes at the expense of long-term skill development. Selling skills—such as prospecting, qualification, negotiation, and closing — are essential for sustained success in sales, yet they frequently receive less attention for several reasons:

  1. Time Constraints: Sales leaders are often pressed for time, balancing numerous responsibilities that span operational management, strategic planning, and personnel development. In this high-pressure environment, allocating time for regular skill coaching can seem less immediately rewarding than deal coaching.
  2. Short-term Focus: The intense focus on meeting immediate sales targets can lead SaaS leaders to prioritize quick wins over long-term development. This short-termism can result in a cycle where teams rely on leader intervention in deals rather than becoming self-sufficient through improved selling skills.
  3. Underestimation of Impact: Some leaders may not fully appreciate the cumulative impact of enhanced selling skills on overall team performance. By improving individual competencies, teams can handle a broader range of selling situations independently, reducing the bottleneck effect of needing leader input on each significant deal.


What SaaS Sales Leaders Should Be Doing Better

To foster a more balanced and effective sales strategy, SaaS sales leaders should integrate skill development into their coaching paradigms. Here’s how:

  1. Incorporate Skill Development into Routine Coaching: Leaders should ensure that each coaching session includes components of skill development tailored to the representative’s specific needs and weaknesses. This approach helps build the rep’s capability to handle similar situations independently.
  2. Leverage Technology for Scalability: Utilizing sales enablement and coaching technologies can help leaders efficiently deliver personalized skill development at scale. These technologies can provide actionable insights based on data from sales interactions, allowing leaders to pinpoint areas for improvement and track progress over time.
  3. Create a Culture of Continuous Learning: Encouraging a learning-oriented culture within the sales team can foster an environment where continuous improvement is valued over short-term gains. This shift can be achieved through regular training sessions, peer learning, and incentivizing skill advancement alongside achieving sales targets.
  4. Balance Metrics: While immediate sales metrics are crucial, leaders should also track and reward improvements in selling skills. Metrics such as call quality, customer engagement levels, and conversion improvements can indicate skill development and motivate reps to focus on honing their abilities.
  5. Lead by Example: Sales leaders should demonstrate their commitment to skill development by actively engaging in training sessions and sharing their experiences and insights. This leadership by example, reinforces the importance of skill development and aligns the entire team toward a common goal of comprehensive excellence.



While deal coaching is important for closing immediate sales, neglecting selling skills can undermine long-term success. SaaS sales leaders must strive for a balanced approach that focuses on closing deals and developing the skills that enable sales teams to thrive independently in a competitive market. By doing so, they enhance their team’s capability and drive sustainable growth and resilience in an ever-evolving sales landscape.


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Steven Rosen 2022

Hi, I’m Steven Rosen, and I’ve been coaching sales executives for over 20 years!


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Steven Rosen - Executive Sales Coach


Steven A. Rosen

Steven helps companies transform sales managers into great sales leaders. His focused coaching helps clients achieve greater personal and professional success. Steven is the author of 52 Sales Management Tips - The Sales Manager’s Success Guide.

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