Customer Success vs Sales: How Commercial Skills Drive Better Retention & Growth

How to Upskill as a CSM: Developing Sales Skills for Customer Success

Customer Success Managers (CSMs) are playing an increasingly critical role in revenue growth. With companies facing pressure to maximise revenue from existing customers, CSMs must go beyond relationship management and develop strong commercial skills. Whether responsible for renewals or expansion, mastering sales skills is essential for career growth and business impact.

In this article, we’ll break down the key selling skills for Customer Success Managers and provide actionable steps to develop them, featuring insights from leading CS coaches and experts, including Anika, Renata, Saori, and Marc.

Customer Success vs Sales: Why CSMs Need ‘Sales’ Skills

The relationship between Customer Success and Sales has evolved significantly. While traditional Sales teams focus on customer acquisition, CSMs play a crucial role in ensuring long-term retention and expansion. Businesses are recognising that existing customers are a primary source of revenue growth, leading to increased expectations for CSMs to drive commercial conversations and unlock revenue growth. This shift has blurred the lines between the two functions, requiring CSMs to adopt core sales skills without losing sight of their customer advocacy role. Understanding how to position value, navigate renewal discussions, and identify expansion opportunities is now a key part of being an effective CSM.

Marc believes the days of CSMs being purely relationship managers are over:

Businesses now expect CSMs to be revenue drivers, proactively identifying opportunities for retention and growth. The ability to have commercial conversations is what differentiates a high-performing CSM from the rest."

Saori explains why renewals still require strong commercial acumen:

"Renewals are not just transactions; they are about securing long-term partnerships. Strong commercial acumen enables CSMs to strengthen value positioning and proactively manage risks. When CSMs develop the ability to engage stakeholders and communicate value confidently, they not only secure renewals but also position themselves for leadership roles in the future."

Anika highlights the challenge many CSMs face:

"Many CSMs worry about being too ‘salesy,’ but the best CSMs understand that selling isn’t about pushing—it’s about helping. If you genuinely believe in your product’s value, then having commercial conversations is a natural extension of your role."

Is Customer Success Sales? Not exactly—but sales and Customer Success are more intertwined than ever. Traditionally, sales teams focus on acquiring new customers, while CSMs manage retention and growth post-sale.

However, as Renata points out: 

"Many companies are struggling to meet their sales targets, and since CSMs are revenue owners, their commercial skills directly contribute to a company’s success. CSMs manage what is often the largest share of a company’s revenue—existing customers. Given their deep understanding of customer challenges and needs, they are in the best position to identify, progress, and convert expansion opportunities."

“I wouldn’t call it a sales mindset—I’d call it a value mindset. Where there is value, revenue follows. One challenge is that, for many, this is an entirely new skill set, and developing it can feel uncomfortable or awkward at first. Another challenge is balancing retention-focused activities with expansion opportunities, often while managing internal demands and customer expectations.”

Key Sales and Customer Success Skills for CSMs

To excel in a revenue-driven role, CSMs must develop a combination of strategic thinking, communication, and commercial acumen. Customer Success is no longer just about building relationships—it’s about driving measurable value for customers while contributing to business growth. Strong sales skills enable CSMs to navigate complex conversations, align solutions with customer needs, and ultimately impact retention and expansion. By mastering discovery techniques, commercial confidence, negotiation, and stakeholder engagement, CSMs can transition from being reactive support professionals to proactive growth partners. Below are the most critical skills every CSM should focus on developing.

To excel in a revenue-driven role, CSMs should focus on developing these core sales skills:

• Strong discovery skills – The ability to uncover business pain points and growth opportunities, what truly matters to the customer and what will have the biggest impact. When you find the value, the path to growth becomes clearer.
• The ability to zoom out – Balancing long-term strategic goals with short-term targets.
• Confidence in commercial conversations – Talking about revenue, competent in negotiations and at handling objections to navigate difficult renewal or upsell discussions, and be able to position value with conviction.

• Storytelling to frame expansion conversations in a way that feels natural.

• Stakeholder engagement & multithreading – Engaging decision-makers beyond daily contacts ensures renewals and expansions are driven by long-term business goals.
• Proactive risk & opportunity management – Identifying churn risks early and surfacing expansion opportunities at the right time allows CSMs to influence revenue outcomes well before renewal discussions begin.
  

Discovery Skills: Uncovering Business Needs as a CSM

Discovery is the foundation of any successful Customer Success strategy. Without a deep understanding of customer goals, challenges, and evolving needs, CSMs risk missing key opportunities for retention and expansion. Strong discovery skills enable CSMs to uncover critical insights that drive impactful conversations, positioning them as strategic advisors rather than reactive account managers. The best CSMs make discovery an ongoing process—continuously refining their approach and adapting their solutions to meet customer needs in real time.

A successful CSM renewal strategy starts with great discovery. Renata highlights this as the most critical skill:

"The ability to uncover what truly matters to the customer and what will have the biggest impact. When you find the value, the path to growth becomes clearer. Discovery isn't about asking standard questions—it’s about listening deeply, challenging assumptions, and helping customers articulate their business objectives in a way that connects to your product."

Marc emphasises why discovery is vital for customer retention and expansion:

"The best CSMs ask the right questions at the right time. A great discovery process is not a one-time thing—it’s an ongoing conversation where you continually refine your understanding of the customer’s evolving needs and align your solution accordingly."

Saori discusses the mindset shift required:

"CSMs often think of discovery as something only Sales does. In reality, every great CSM is constantly discovering new insights about their customer. The difference is that top CSMs act on these insights to drive meaningful conversations."

Anika shares a practical approach:

"Approach every customer conversation with curiosity. Ask open-ended questions, actively listen, and don’t be afraid to challenge assumptions. Your job isn’t just to support customers—it’s to help them think bigger."

Confidence in Commercial Conversations

Many CSMs struggle with commercial conversations because they fear coming across as too sales-focused. However, confidence in discussing pricing, value, and expansion opportunities is essential for securing renewals and driving customer growth. The key to success is shifting the mindset from ‘selling’ to ‘helping.’ When CSMs understand that commercial discussions are an extension of their role as trusted advisors, they become more comfortable and effective in these interactions. Developing confidence takes practice, but when done right, it strengthens relationships and reinforces the value of the solution being provided.

Renata believes CSMs often worry about discussing revenue, but emphasises commercial conversations don’t have to feel transactional:

"The key is to reframe these discussions as value-driven. When customers see that you genuinely care about their success, revenue discussions feel like a natural extension of that relationship."

Marc believes confidence as a CSM comes from knowing that you are providing something that will make their business better:

"If you don’t believe in your solution’s value, neither will your customer. Confidence comes from knowing that you are providing something that will make their business better. The best way to build confidence is practice—role-play, test different approaches, and refine your pitch."

Saori explains Commercial confidence isn’t about being aggressive—it’s about being assertive:

"If you’re afraid to discuss pricing, customers will sense that. Instead, focus on the outcomes you deliver, and talk about cost in terms of investment and return."

Anika believes CSMs need to get comfortable with silence:

"When you state your price or propose an expansion, don’t rush to fill the silence. Let the customer process the information—it’s in these moments that real conversations happen."

Negotiation and Objection Handling

CSMs often find negotiation challenging because they associate it with conflict. However, negotiation is not about winning or losing—it’s about reaching an agreement that works for both the company and the customer. Effective objection handling builds trust and ensures that the conversation stays focused on value rather than price alone. When approached correctly, negotiation is an opportunity to reinforce the customer’s investment, alleviate concerns, and ensure both parties feel they are making a mutually beneficial decision. Mastering this skill allows CSMs to navigate difficult conversations with confidence and credibility.

Renata believes you should view objections are a sign of interest:

"If a customer is pushing back, it means they’re considering their options. The best CSMs know how to handle objections by reinforcing value, rather than immediately conceding."

Marc explains that you shouldn't view negotiation as winning or losing:

It’s about alignment. Find common ground and help the customer see that your solution is in their best interest. If you approach negotiations collaboratively, customers will respect and trust you more."

Saori believes that many CSMs see negotiation as a battle, so they choose to avoid it. She believes CSMs need to challenge their own perspective on this:

"Negotiation isn't about conflict, it’s about problem-solving. The key is to ask the right questions and ensure both sides feel like they are gaining value."

Anika believes the best way to handle objections is to anticipate them:

"If you know what common objections are, you can prepare responses that turn hesitation into commitment."

Customer Success Coaching

Developing sales skills as a CSM is not a one-time event—it’s an ongoing process. Continuous coaching, practice, and feedback help refine these skills and build confidence over time. Organisations should prioritise structured training and mentorship to ensure CSMs have the right tools to drive revenue effectively.

Many CSMs struggle with how to introduce commercial conversations without disrupting their customer relationships. Negotiating and handling objections can also feel uncomfortable, as CSMs are often relationship-driven individuals who don’t like saying “no” to customers. Coaching helps them navigate this balance while maintaining trust.

Marc believes many CS teams receive limited training and budget for commercial skills development:

"Unlike Sales, which benefits from structured training, CS teams often lack dedicated resources for commercial enablement. As a result, CSMs are expected to contribute to revenue without the same level of investment in their professional growth."

How Customer Success Coaching Can Support CSMs:

Role-Playing Real-Life Scenarios

The best way to develop commercial skills is through repetition and reinforcement—whether through role-playing exercises, peer coaching, or learning from experienced sales professionals. By fostering a culture of continuous improvement, CSMs can become more effective in their commercial conversations and drive greater impact for both customers and the business.

Renata explains the best way to develop these skills:

"Practice, practice, practice. Coaching provides a safe space for CSMs to talk through real scenarios, allows them to role-play conversations and prepare for unexpected challenges without consequence. The more you practice objection handling, renewal conversations, and expansion discussions, the more natural and confident you will feel in front of customers."

Reframing Mindsets and Building Confidence

 A key part of this is mindset reframing—helping CSMs understand that being commercial and being a trusted partner to their customer are not mutually exclusive.

Many CSMs worry about coming across as pushy or too focused on revenue instead of relationships. They often lack confidence in commercial conversations and struggle to connect customer outcomes to expansion opportunities. Coaching supports CSMs in challenging their outlook on this, and helps them to see things differently for their own advantage.

Impostor syndrome is also a notable issue that often goes undiagnosed in Customer Success. 

One of our expert Customer Success coaches Paul Lucherini has his suspicions as to why this is:

"Because Customer Success is so new, a lot of people suffer from impostor syndrome. They don't have the guidance back to previous experience."

Saori believes this shift isn’t about adopting a 'sales' mindset—it’s about recognising the commercial value CSMs already bring:

Many CSMs don’t realise that they are already influencing revenue in their daily work. By reframing their role, they can become more confident and proactive in having commercial discussions."

Marc Tells us:

As a holistic wellness coach, I’ve seen how mindset, confidence, and clarity play a crucial role in both professional and personal growth. The shift isn’t about “adopting a sales mindset”—it’s about recognising the commercial value CSMs already bring and developing the confidence to engage in these discussions with purpose.

Common Approaches For Coaching CSMs to Develop Sales Skills

Expert Coach Anika explains she takes a structure-first, strategy-driven approach, to ensure CSMs have the right foundation to apply commercial skills with confidence and intention.

She emphasises the importance of mastering time management & self-care for long-term success:

Commercial conversations require clarity and headspace. I help CSMs structure their workday, manage priorities, and build an environment where they can bring their best self to their role without feeling overwhelmed.

Mastering communication skills is also key for Anika:

"Strong communication is essential for career growth. I coach CSMs on engaging stakeholders, positioning value confidently, and navigating conversations in a way that feels natural and strategic."

Measuring The Impact of Coaching on CSM Performance?

It can be difficult to measure ROI of coaching. But how can you track and measure the impact on performance, especially when a lot of the changes are mindset related? Our experts explain some ways to do this:

• Track expansion revenue influenced by CSMs and how often they identify or assist in upsell opportunities.
• Behavioural indicators: Call and meeting reviews, as well as self and peer assessments, to track skill development over time and ensure coaching techniques are being applied.
• Leading indicators: Increased confidence in commercial conversations, improved customer engagement, and more proactive identification of opportunities.
• Lagging indicators: Retention and renewals, expansion revenue, win rate, and deal progression—all of which should improve as a result of stronger commercial skills.
  
  
  

The Future of Customer Success for SaaS: Evolving Beyond Retention and Driving Expansion

As SaaS companies continue to shift toward a recurring revenue model, the role of Customer Success is evolving beyond just retention. Businesses are now looking to CSMs to actively drive expansion, influence renewals, and maximise customer lifetime value. This evolution requires a mindset shift—from being solely focused on customer happiness to being a strategic revenue partner. The future of Customer Success lies in balancing advocacy with commercial acumen, ensuring that customers achieve their goals while also contributing to the company’s bottom line. By embracing this new reality, CSMs can position themselves as indispensable assets within their organisations.

Anika believes CSMs should seek to learn from Sales Teams:

"Align closely with account executives and sales leaders to create a shared strategy for customer growth. CSMs have invaluable customer insights, and when they collaborate effectively with Sales, they ensure that outreach is well-timed and relevant. Sitting in on sales calls, co-selling, and sharing customer insights are great ways to strengthen these skills."

Marc believes Customer Success is no longer just about retention—it’s about revenue:

T"he most successful CSMs don’t just react to customer needs; they proactively shape customer growth."

Only Responsible For Renewals? Here's Why CSMs Should Still Develop Their Commercial Skills

Even if a CSM is not driving expansion, they still need to showcase the value of the product to secure renewals. Understanding commercial skills like negotiation, positioning ROI, and handling objections helps CSMs influence decision-makers and protect/grow revenue. Renewals are not just transactions; they are about securing long-term partnerships. Strong commercial acumen enables CSMs to:

• Strengthen value positioning – Ensuring customers see the long-term impact of their investment.
• Proactively manage risks – Addressing churn signals early rather than waiting for last-minute renewal negotiations.
• Enhance career growth – Developing commercial confidence, stakeholder engagement, and strategic thinking—skills that are transferable beyond CS and valuable for leadership roles.
  

As Renata says:

"Where there is value, revenue follows."

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TL;DR: How to Upskill as a CSM and Master Sales Skills

Customer Success Managers (CSMs) are now expected to drive revenue, not just manage relationships. To excel in today’s landscape, CSMs must develop key sales skills, including:

• Discovery Skills: Uncover customer needs and align solutions with their goals.
• Confidence in Commercial Conversations: Shift the mindset from selling to helping, ensuring value-driven discussions.
• Negotiation & Objection Handling: Address concerns effectively, keeping conversations focused on business impact.
• Storytelling for Expansion: Use real-world examples to frame upsells and renewals naturally.
• Stakeholder Engagement: Build relationships beyond day-to-day contacts to secure long-term success.

How to Develop These Skills:

• Role-playing & coaching to practice real scenarios.
• Reframing the mindset to see commercial conversations as customer advocacy.
• Collaborating with Sales teams to align strategies and refine techniques.
  

The Future of Customer Success:

CSMs are evolving into revenue influencers, making sales skills essential for retention and expansion. The most successful CSMs balance advocacy with commercial acumen to drive customer growth and business success.

👉 Bottom Line: CSMs who master commercial skills will not only increase customer value but also accelerate their own career growth.