Building Your Retention Playbook

A hybrid course, tactical sprint to increase renewals with smarter systems and sharper strategy.

This 4-week course helps revenue and customer leaders reduce churn and boost renewal precision—without relying on reactive save campaigns. Through expert-guided content and peer-calibrated frameworks, you’ll develop strategic retention models, playbooks, and forecasting systems customized for your business.

Course details

Session dates: July 30 – August 20
Time: Wednesdays, 3:00 PM to 4:30 PM ET
Open to: Executive Members
Hybrid Format: On-demand content + live 90-minute sessions

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Stop fighting churn with last-minute fixes.

Clarify what's working (and what's not).

Pinpoint the systems and signals that drive your current retention rates—then optimize them with purpose.

Architect playbooks by segment.

Design tiered strategies for Enterprise, Mid-Market, and SMB renewals—mapped to your business model, deal structures, and team strengths.

Execute through alignment.

Structure your CS org and workflows to drive consistent outcomes—not fire drills.

Jan Young - Build Your Retention Playbook

Jan Young, Instructor

Jan is an award-winning Customer Success leader who has transformed CS leaders into award-winning executive team leaders. She has served as VP of Client Services for two successfully exited startups.

Since 2016, Jan has been coaching and advising founders, startups, and Customer Success leaders on increasing revenue, go-to-market alignment, and customer-led growth. Her holistic approach has developed over time working in technology and startups since 2001 in various roles, including Marketing, Sales, Account Management, Project Manager, Product Owner, Professional Services, and Customer Success.

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What to expect from a Hybrid format.

Pavilion’s hybrid format is built for high-performing operators who value both flexibility and peer insight. Each week, you’ll get focused on-demand learning modules you can complete on your schedule—followed by live 90-minute sessions designed for real conversations.

On-demand, on your terms.

No need to block your calendar for lectures. Digest expert insights when your mind’s clear and time allows.

Live sessions that drive real outcomes.

Every week, join high-signal discussions guided by your instructor and shaped by breakout groups of peers solving the same problems.

Community when you need it.

A private Slack channel gives you space to share wins, get feedback, and dig deeper—all at your own pace.

Course curriculum

This course is for CROs accountable for CS, CMOs seeking post-sale visibility, and CS leaders building retention strategy from scratch.

Curriculum and instructor lineup subject to change.

Session 1:
Retention Assessment

By the end of this class, you will be able to:

Identify your retention rates correctly
Identify the processes you use to retain your customers successfully
Improve customer retention by identifying and correcting systemic challenges

Session 2:
Retention Strategies & Playbooks

By the end of this class, you will be able to:

Build your strategies and playbooks for Enterprise vs Mid-Market vs SMB
Build your strategies and playbooks for monthly, annual, and multi-year deals and variations of business models

Session 3:
Team Structure, Workflows, Communication, Training

By the end of this class, you will be able to:

Identify challenges in your current system and identify your optimal team structure
Build a plan to address any challenges or communication gaps in your current workflows
Build your optimal team structure by identifying any needed tools, processes, and skill gaps

Session 4:
Projections vs Quotas

By the end of this class, you will be able to:

Identify key factors and data contributing to and signal renewals for your customer base and product(s)
Build renewal projections, quotas, and pipelines for your business model, customer base segments, and product(s)

Turn retention into a growth lever

Walk away with a fully built retention strategy and system—custom-fit to your GTM structure.

Stop churn before it starts – Eliminate reactive saves with early-warning triggers and systemic prevention
Drive board-level confidence – Forecast renewals with precision and back it up with process
Cross-functional fluency – Design strategies that align CS, Sales, and Marketing
Immediate value – Use every session to sharpen strategy and build systems that last

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Course FAQ

: CROs, CMOs, and CS leaders who need to improve retention performance with rigor, structure, and scale—especially those new to post-sale ownership.
Not a member? Join now.
: No. This course is ideal for executives with ownership of CS outcomes but no hands-on retention background.
: Four 90-minute sessions, plus 30–60 minutes of weekly on-demand content. Apply as you go—no extra homework.
: Hybrid. On-demand modules prepare you. Live sessions help you build and apply what you’ve learned in real time.
: Yes. A course completion badge is available for those who attend the live sessions and complete deliverables.
: Recordings will be available after each class. You’ll also receive course materials and templates.
: It’s included in your Pavilion membership.