Beyond Onboarding: Building an Amazing Ongoing Training Program for Your CS Team
By Kristen Hayer
When leaders think about customer success training, the conversation almost always starts with onboarding. Some lucky new hires get a well-structured introduction to the company, its products, and its customers. They complete their 30-60-90 plans, attend kickoff sessions, and dive into the basics of customer success.
Then, too often, the learning stops.
Ongoing training rarely receives the same attention or investment as onboarding, even though it is what turns capable CSMs into confident, strategic professionals. If onboarding builds competence, ongoing training builds confidence, and that is what drives true customer success.
Why Ongoing Training Matters
Customer success evolves constantly. Customer expectations shift. New technology changes how we deliver value. Companies refine their strategies, expand into new markets, and reorganize teams. In this kind of environment, a single burst of onboarding training is not enough.
Research from LinkedIn Learning’s 2024 Workplace Learning Report found that employees at organizations with strong learning cultures are 57% more likely to stay with your company and 23% more likely to move into new roles internally. In other words, when people keep learning they grow, and so does the business.
For CSM teams, continuous training offers tangible benefits. It increases retention, improves confidence in customer conversations, and strengthens collaboration across departments. More importantly, it shows your team that you are invested in their long-term development, not just their immediate performance.
When companies make learning a part of their culture, they create an environment where curiosity and innovation thrive.
What Great Ongoing Training Looks Like
Most teams already have some kind of ongoing training. It might be an occasional lunch-and-learn, a new product demo, or a quarterly meeting. Those efforts are valuable, but they are not enough on their own.
An effective ongoing training program is structured, consistent, and closely tied to company goals. It balances formal instruction with peer learning and real-world application. Great programs share a few common elements:
Relevance: Training topics align with the challenges CSMs face every day and the company’s broader strategy.
Variety: Use a mix of peer learning, internal workshops, and short-form content to reach different learning styles.
Frequency: Maintain a regular cadence - monthly or quarterly - so learning becomes a habit, not an interruption.
Measurement: Focus on impact, not just attendance. Track whether new skills show up in customer outcomes, renewal rates, or internal collaboration.
As your company grows and your customers evolve, so should your training program. Ongoing learning should be a living, breathing part of your culture.
How to Build a Sustainable Program
You do not need to create a massive enablement initiative overnight. Start small and build from there. Here are some practical steps to design an ongoing training program that lasts:
Start with a skills map. Identify what CSMs need to know today and what they will need to know next year. Look at where your team is strong and where there are gaps.
Ask your team. Survey your CSMs to understand what topics would make them more effective. Their feedback will help you prioritize what matters most.
Leverage internal expertise. Invite high-performing CSMs, Product Managers, or Sales leaders to share knowledge. Internal voices make training feel grounded and relevant.
Set a sustainable cadence. Even a one-hour session each month can keep learning active without overwhelming your team.
Track and iterate. Collect feedback and adjust topics regularly. Training should evolve along with the business.
By following these steps, you can create a rhythm of learning that supports both individual growth and organizational success.
Action Items for CS Leaders
Audit your current training cadence: Is learning happening beyond onboarding?
Identify one skill gap that is holding your team back and design a short workshop around it.
Pair newer CSMs with experienced mentors for ongoing peer learning.
Partner with HR or enablement to align CS development with company-wide learning goals.
Celebrate small learning wins and publicly reinforce a culture of curiosity and growth.
Why This Matters
Ongoing training is more than a management best practice. It is a reflection of your company’s values. When you invest in the continued growth of your team, you demonstrate that customer success is not just about renewals or metrics. It is about people who are capable, confident, and continually improving.
When I wrote The Customer Success Talent Playbook, my focus was on building strong onboarding programs. But the more I work with CS leaders, the more I see that what separates great teams from good ones is what happens after onboarding ends.
Training should not be a one-time event. It should be a continuous process of growth; one that helps your team evolve right alongside your customers. Because in customer success, learning never stops.
Need training? The Success League can help! We offer both CSM and Leadership certification programs, as well as corporate training. Visit TheSuccessLeague.io for our full offerings or reach out to us with any questions.
Kristen Hayer - Kristen founded The Success League in 2015 and currently serves as the company's CEO. Over the past 25 years Kristen has been a success, sales, and marketing executive, primarily working with scaling tech companies, and leading several award-winning customer success teams. She has written over 100 articles on customer success, and is the host of 3 podcasts about the field. Kristen has served as a judge for the Customer Success Excellence awards, and is on the board of several early-stage tech companies. She received her MBA from the University of Washington in Seattle, and now lives in San Francisco.
