Skip to content

2. Internal Organisational Challenges

a) Sales & CSM Ownership Conflicts

Scenario:
Sales teams often want to maintain primary customer contact, leading to conflicts over customer ownership.

Industry Insight:

  • Friction between Sales and Customer Success leads to missed opportunities and low customer satisfaction (momentum, 2024).

Strategies to Overcome This Challenge:

1. Clear Handover Process: Define roles post-sale.
2. Joint Engagements: Align Sales & CS efforts.
3. Internal Playbooks: Document customer management boundaries.

Role-Playing Exercise:

  • Objective: Define post-sales responsibilities with Sales to prevent conflicts.
  • Instructions:
  • Sales Rep: "I want to keep managing the customer relationship so I can upsell later."
  • CSM: "I see the value in ongoing collaboration. How about we establish a structured handoff where I handle adoption and retention, while you focus on expansion opportunities?"
  • Sales Rep: "That could work, but I don’t want to lose visibility into my accounts."
  • CSM: "We can schedule joint quarterly check-ins so you stay informed, and I can provide usage insights to support your upsell strategy."

b) Escalations Due to Mis-Sold Features & Expectations

Scenario:
Customers are sold features that do not exist or do not meet their needs.

Industry Insight:

  • Sales overpromising to close deals were linked to misaligned expectations and damaged customer relationship (momentum, 2024).

Strategies to Overcome This Challenge:

1 Align with Sales on ICP: Ensure accurate targeting.
2. Expectation Management Early: Reset incorrect assumptions.
3. Shift the Conversation: Focus on maximizing existing product value.

Role-Playing Exercise:

  • Objective: Handle a conversation with a customer who was mis-sold a feature.
  • Instructions:
    • Customer: "We were promised this feature, but it’s not working as expected!"
    • CSM: "I understand your frustration. Let me clarify what’s available and explore a workaround or an alternative solution."
    • Customer: "We need this functionality. If we can’t get it, we might need to look elsewhere."
    • CSM: "I hear you. Let me escalate this to the product team, and we can explore roadmap options or potential integrations."

c) Inflexible Processes Impacting Customer Retention

Scenario:
Rigid billing and contract policies prioritize immediate revenue over long-term retention.

Industry Insight:

  • Operation inflexibility will have a negative direct impact on your brand reputation (Thepowerscompany, 2023).

Strategies to Overcome This Challenge:

1. Retention-Focused Billing Policies: Work with finance to introduce flexible payment options.
2. Proactive Renewal Discussions: Engage customers early to avoid last-minute contract conflicts.
3. CSM Advocacy: Escalate customer concerns internally to balance financial goals with customer retention.

Role-Playing Exercise:

  • Objective: Address customer concerns regarding inflexible payment policies.
  • Instructions:
    • Customer: "Our budget has been cut, and we need to reduce our spending. Can you offer a discount?"
    • CSM: "I understand the financial challenges. While we don’t typically offer discounts mid-contract, we do have flexible payment options. Would a payment installment plan help?"
    • Customer: "That might work, but we’re still concerned about long-term costs."
    • CSM: "Let's explore how we can optimize your usage to ensure you’re getting the most value from your subscription."