Creating a Quarterly Cadence for Training CSMs and How to Pay for It
By Allison Tiscornia
Now that we are coming out of SKO season, it is time to get to work. You have set your quarterly and annual goals. You have aligned with Product and Sales. You are partnering with Marketing on your customer communications cadence, and you are working with CS and Rev Ops to update your 2026 playbooks. Your strategy and tactics are set.
But pause for a moment. How are you going to get your team ready to actually execute on all of this?
Setting up a thoughtful training calendar with your Enablement team is the next critical step to delivering results while still hitting your financial targets and protecting your eNPS.
Put a Quarterly Training Cadence in Place (Before the Quarter Starts Eating You Alive)
Training cannot be an ad hoc activity that gets squeezed in between QBR prep and renewal fire drills. If you want your strategy to survive contact with reality, enablement has to be planned with the same rigor as your revenue forecast.
A quarterly training cadence gives you three things most CS organizations are desperately short on:
Predictability for your team
Focus for your enablement efforts
A defensible budget narrative for Finance
At a minimum, each quarter should include three distinct types of training, each with a clear purpose.
1. Foundation Refresh (Quarterly, Mandatory)
Every quarter should begin with a short reset on the fundamentals: your CS methodology, value framework, and operating expectations. This is not onboarding content. It is about tightening execution, aligning language, and reinforcing what “good” looks like now, not last year.
Ask questions like:
How do we run success plans today?
How do we articulate value and outcomes consistently?
How do we prioritize accounts when capacity is tight?
These sessions are especially critical after SKO, major product launches, or pricing and packaging changes, when CSMs are absorbing mixed signals from across the company.
2. Skill-Based Enablement (Quarterly, Rotating Focus)
Each quarter should focus on one clearly defined skill tied directly to your business goals. Not ten topics. One.
Examples:
Q1: Running executive-level conversations
Q2: Expansion discovery and value justification
Q3: Risk identification and remediation
Q4: Renewal strategy and commercial confidence
Depth beats breadth every time. One skill practiced, role-played, and reinforced over a full quarter will outperform a scattershot approach that creates awareness but no lasting behavior change.
3. Tooling and Process Updates (As Needed, Time-Boxed)
Dashboards, health scores, playbooks, and AI tools matter. They just should not hijack your entire enablement calendar.
If a new tool or process cannot be explained, practiced, and applied in under 60 minutes, it is not enablement-ready.
Reinforce It, or It Will Not Stick
Training that happens once is an event. Training that gets reinforced becomes muscle memory.
Build reinforcement into the quarter through:
Manager-led coaching prompts tied to the training theme
Call reviews or deal reviews using the new framework
Lightweight certifications or practical assignments
This is where enablement, CS leadership, and frontline managers either align to achieve the strategy or quietly undermine it.
“But How Do I Pay for All This?”
This is where many CS leaders get stuck and where they often undersell themselves.
Training is not a discretionary expense. It is a capacity multiplier.
To make the math work:
Anchor enablement to outcomes Finance already tracks. Reduced churn, faster time-to-value, improved expansion rates, and lower regretted attrition are all financially material. Training that improves execution directly impacts these metrics.
Shift from one-time events to reusable assets. Recorded sessions, internal facilitators, peer-led workshops, and enablement partners who specialize in Customer Success can help you create practical, repeatable programs that scale without overwhelming your team or your budget.
Budget quarterly, not annually. A quarterly approach allows you to test, adjust, and prove ROI in smaller increments, which is far easier to defend than a large upfront investment.
And one more thing leaders often forget: burned-out CSMs are expensive. Missed renewals, attrition, backfills, and lost customer trust cost far more than doing enablement right the first time.
Pro tip: include your annual attrition costs from HR when building your enablement business case. It makes the trade-offs painfully clear.
Turning Strategy Into Execution
Your CSMs are being asked to do more than ever: manage more accounts, drive more value, sell more effectively, and operate with increasing efficiency. Handing them a strategy deck and hoping for the best is not leadership.
A thoughtful quarterly training cadence turns strategy into execution, execution into consistency, and consistency into results.
If you want your plans to survive beyond SKO season, invest in preparing the people who have to carry them out. Training is not a nice-to-have. It is how you make the plan actually work.
The Success League is a Customer Success training and consulting firm focused on building to performing CS programs. We offer a full array of training, from CSMs to CS Leaders, to the VP/Director level. If you or your team could benefit from training, we would love to help! Discover more here.
Allison Tiscornia - Allison is a seasoned Silicon Valley executive with over 20 years of experience leading customer-facing teams. As Chief Customer Officer at ChurnZero, she scaled the customer experience organization and formalized implementation methodologies. At Sendoso, she built the customer experience function before transitioning to Chief Sending Operations Officer, aligning logistics with product and customer workflows. Previously, as VP of Customer Services at Zenefits, she led professional services and support for the platform. Passionate about scaling teams and driving customer success, Alli has held leadership roles at Medallia, Visa, Endeca (acquired by Oracle), and CA Technologies. She holds a B.A. in sociology and public policy from the University of Arizona, with certifications in scrum management, project management, and IT infrastructure. As a visiting lecturer at Pavillion’s CCO School, Alli specializes in customer onboarding. She resides in Scottsdale, Arizona, with her family and a lively Goldendoodle.
