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Module 4: Overcoming Common Challenges for a CSM

Learning Objectives: 

    • Address customer-specific issues like disengagement and product gaps.
    • Resolve internal conflicts with teams like Sales and Product.
    • Proactively manage external challenges, including economic and regulatory pressures.
Overcoming Common Challenges
29:38

Introduction:

Customer Success Managers (CSMs) navigate a variety of challenges, both customer-facing and internal, that impact customer retention, satisfaction, and product adoption. Below, we explore these common roadblocks in depth, incorporating industry data, case studies, and role-playing exercises to strengthen problem-solving skills.

1. Customer-Specific Challenges

a) Customer Skill & Product Knowledge Gaps

Scenario:
A customer purchases an enterprise SaaS tool but struggles with implementation due to a lack of technical expertise, leading to delayed onboarding and low adoption.

Industry Insight:

  • Only 38% of the industry has implemented an adoption framework. Those organizations that have built this framework have achieved improvements in retention expansion, churn, NPS, and a reduction in employee attrition to name a few(TSIA, 2024).

Real-World Example:

  • HubSpot Academy Success Model: HubSpot introduced a free certification program for its CRM users, resulting in a an increase in self-sufficient users and reducing support dependency.

Strategies to Overcome This Challenge:

1. Tailored Learning Paths: Offer customized training modules based on user roles and experience levels.
2. On-Demand Resources: Provide a self-service knowledge base, FAQs, and how-to videos.
3. CSM-Led Office Hours: Host regular Q&A sessions to provide real-time guidance.

Role-Playing Exercise:

  • Objective: Address a competency gap with a customer.
  • Instructions:
    • Customer: "We’re struggling to implement the analytics dashboard—it’s too complex."
    • CSM: "I understand. Have you had a chance to go through our guided onboarding? I can also arrange a hands-on session tailored to your use case."
    • Customer: "That would be helpful, but we also don’t know which reports to use."
    • CSM: "I’ll schedule a walkthrough of key reports used by similar businesses and set up a follow-up session for Q&A."

b) Confusion Around the CSM Role & Responsibilities

Scenario:
A mid-sized fintech company frequently directs support tickets to their CSM, assuming they handle technical troubleshooting.

Industry Insight:

  • CSMs who set clear expectation about the nature of their role to the customer succeed in keeping their customer engaged (successcoaching, 2024).

Real-World Example:

  • Salesforce’s CSM Role Differentiation: Salesforce clarified CSM vs. Support roles by embedding a chatbot-driven support flow in its CRM, reducing CSM misrouted requests.

Strategies to Overcome This Challenge:

1. Clarify Roles During Onboarding: Use a role overview slide.
2. Automate Triage: Implement ticketing workflows to route queries properly.
3. Create an FAQ Playbook: Address common role-related questions proactively.

Role-Playing Exercise:

  • Objective: Handle a scenario where a customer sends a support request to the CSM.
  • Instructions:
    • Customer: "Hey, our system is down—can you fix this?"
    • CSM: "I hear your concern, and I want to ensure you get the fastest resolution. Let me connect you with our support team, who can resolve this quickly. In the meantime, I’ll track the case and keep you updated."
    • Customer: "Can’t you just escalate it?"
    • CSM: "Absolutely, I’ll ensure the right team is involved, but technical troubleshooting is best handled by our dedicated support specialists. That way, we get you back on track ASAP."

c) Product Feature Gaps

Scenario:
A customer requires specific features that your product currently lacks, leading them to consider alternative solutions.

Industry Insight:

  • Building the relationship between product management and customer success to deliver closed-loop feedback to customers yields higher returns on ARR. In some cases, companies yielded a 26% higher ARR (TSIA, 2024).

Strategies to Overcome This Challenge:

1. Feedback Loop: Establish a system for collecting and prioritizing customer feedback on feature requests.
2. Transparent Roadmap Communication: Inform customers about upcoming features and timelines.
3. Alternative Solutions: Suggest workarounds or third-party integrations that can fulfill the customer's needs in the interim.

Role-Playing Exercise:

  • Objective: Manage a conversation with a customer requesting unavailable features.
  • Instructions:
    • Customer: "We need this feature, or we might switch to another provider."
    • CSM: "I understand the importance of that functionality. While that feature is not available today, we do have a roadmap that includes similar enhancements. Would you be open to discussing a workaround in the meantime?"
    • Customer: "That could work, but we really need it soon."
    • CSM: "I'll also escalate this to our product team to highlight the demand and keep you updated on progress."

d) Disengaged Customers

Scenario:
A B2B SaaS company notices a drop in logins and feature usage, and the customer ignores CSM outreach.

Industry Insight:

  • Companies that use multi channel personalised re-engagement strategy see an increase in retention (Maxio, 2024).

Strategies to Overcome This Challenge:

1. Data-Driven Engagement: Use product data to personalise outreach.
2. Exclusive Customer Communities: Create Slack or LinkedIn groups.
3. Strategic Check-Ins: Align outreach with business goals rather than generic follow-ups.

Role-Playing Exercise:

  • Objective: Re-engage a disengaged customer using personalized insights.
  • Instructions:
    • Customer: "I haven’t really had time to explore the product."
    • CSM: "Totally understandable! I noticed that companies similar to yours get the most value from [Feature X]. Would you be open to a quick session on how it can help with your current goals?"
    • Customer: "I guess that could be helpful."
    • CSM: "Great! I’ll also send over a case study from a similar customer who saw a 20% efficiency boost using this feature."

e) Low Product Adoption & Feature Utilization

Scenario:
Customers are using only a fraction of the product’s features, limiting the value they receive and increasing the risk of churn.

Industry Insight:

  • Strong product adoption leads to lower churn rate and higher customer lifetime value. (Userflow,2024)

Strategies to Overcome This Challenge:

1. Adoption Dashboards: Use product usage analytics to identify underutilised features and flag low-engagement customers.
2. Gamification & Incentives: Implement in-product nudges, milestone rewards, and engagement campaigns to encourage deeper adoption.
3. Role-Based Training: Offer targeted training sessions based on user personas (e.g., Admins vs. End Users).

Role-Playing Exercise:

  • Objective: Encourage a customer to adopt underutilised features.
  • Instructions:
    • Customer: "We’re mainly using the basic functionality, but I don’t think we need anything beyond that."
    • CSM: "That’s totally understandable. However, many customers in your industry who expanded usage to [Feature X] saw measurable efficiency gains. Would you be interested in a quick demo to explore if it could benefit your team?"
    • Customer: "Maybe, but we’re already pretty busy."
    • CSM: "I completely understand. To make it easier, I can provide a short video and highlight three specific ways this feature can save time. Would you be open to testing it for a week?"

e) Unclear Customer Success Goals & Expectations

Scenario:
A customer has not defined clear success metrics, making it difficult to measure value, align on objectives, or prove ROI during renewal discussions.

Industry Insight:

  • Companies with clear success metrics in place achieve a better data driven decisions that genuinely impact their business outcomes (propellocloud, 2023).

Strategies to Overcome This Challenge:

1. Success Planning Workshops: Facilitate sessions to define KPIs and business outcomes.
2. Benchmarking Data: Use industry comparisons to help customers understand how they should measure success.
3. Goal Tracking Frameworks: Implement a structured approach within the CRM or a success plan template.

Role-Playing Exercise:

  • Objective: Guide a customer toward defining measurable goals.
  • Instructions:
    • Customer: "We’re just using the tool because it was purchased, but we don’t have clear goals."
    • CSM: "That makes sense. Many customers start that way. Would you be open to a short success planning session to align on key business objectives and define measurable outcomes?"
    • Customer: "That could be helpful. How would we go about it?"
    • CSM: "We’d start by identifying the key challenges your team faces and mapping those to the platform’s capabilities. I can also share industry benchmarks to help set realistic success targets."

f) Frequent Customer Stakeholder Changes

Scenario:
A customer’s main point of contact (POC) frequently changes, disrupting continuity, slowing down adoption, and requiring the CSM to reintroduce value multiple times.

Industry Insight:

  • There is a 51% chance that your account will churn within the next year. That number rises to 65% when the champion lost is a senior executive. (Churnzero, 2024).

Strategies to Overcome This Challenge:

1. Stakeholder Mapping: Engage multiple contacts within the customer organization, including executive sponsors, power users, and decision-makers.
2. Executive Business Reviews (EBRs): Maintain leadership engagement to ensure long-term alignment.
3. Strong Documentation: Maintain detailed notes and success plans that can be easily handed over to new POCs.

Role-Playing Exercise:

  • Objective: Successfully onboard a new POC while reinforcing value.
  • Instructions:
    • Customer (New POC): "I just took over this account, and I’m not sure why we even use your platform."
    • CSM: "Welcome! I’d love to provide you with a quick overview of how your team has been using the platform and the key business goals we’ve been working towards."
    • Customer: "I need to assess whether this tool is essential. Can you prove its value?"
    • CSM: "Absolutely! Let me walk you through the ROI your company has already achieved, highlight usage metrics, and share success stories from similar customers in your industry."

g) Challenges with Product Integration & Compatibility

Scenario:
A customer struggles to integrate your product with their existing systems, leading to frustration and potential discontinuation.

Industry Insight:

  • If a SaaS product fails to adapt to the changing needs of its customers, those customers may outgrow the solution and opt for another (cascadeinsights, 2024)

Strategies to Overcome This Challenge:

1. Dedicated Integration Support: Provide specialized assistance during the integration phase.
2. Comprehensive Documentation: Offer detailed guides and resources to facilitate seamless integration.
3. Regular Check-Ins: Maintain frequent communication to address any integration issues promptly.

Role-Playing Exercise:

  • Objective: Assist a customer facing integration difficulties.
  • Instructions:
    • Customer: "We’re having trouble integrating your platform with our existing software. It keeps failing."
    • CSM: "I understand how critical integration is. Can you share the specific errors you’re seeing? I’ll escalate this to our technical team and ensure you get a dedicated support call."
    • Customer: "We don’t have internal technical expertise to handle this."
    • CSM: "No problem! I can also set up an onboarding session where we guide your team step-by-step on the integration process."

Handling a Customer With Vague Goals

Example of a customer unsure about their specific goals with the product

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