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Tuesdays in the Trenches
Every Tuesday we're sharing our thoughts from the trenches on how you can
drive retention and grow your revenue using your CS team
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The New QBR: Automating Business Reviews that Actually Drive Expansion Revenue
The New QBR: Automating Business Reviews that Drive Expansion Revenue. Rethink QBRs as discovery sessions, not status reports. Unlock expansion opportunities with automation.

Nina Wilkinson
Jan 2811 min read


Founding CSMs: How to Succeed as Your Startup’s First CSM
Your first CS hire can make or break early customer success. Discover the Swiss Army knife traits to hire for, the pitfalls to avoid, and what real Year 1 success looks like—from a founding CSM who survived the chaos.

Nina Wilkinson
Dec 1, 202510 min read


How to Keep Your CSMs Motivated and Productive in December (So You Don't Lose January)
Stop losing January renewals to holiday slowdowns. Proven December tactics for high-touch accounts that protect renewals and drive expansion.

Nina Wilkinson
Nov 17, 20256 min read


How to Sell the Value of Your CS Team (And Get the Headcount You Actually Need)
Tired of capacity planning battles? This guide shows revenue leaders how to justify CS headcount with data that wins board approval and spares you the headache.

Nina Wilkinson
Nov 4, 20258 min read


CSMs vs. AMs: How to End the Chaos and Boost Retention
CSM vs. AM: Defining Roles to Protect Revenue and Improve the Customer Experience

Nina Wilkinson
Oct 21, 20259 min read


The Most Human Part of Customer Success
Parenthood, the ER, and Customer Success: one leader’s weekend that reminds us why CS is about people first — not just NPS, metrics, or automation.

Linnea Olson
Oct 14, 20252 min read


AI in Customer Success: Your Blueprint for Scaling Human Connection (Not Replacing It)
Tactical playbook for SaaS leaders to deploy AI in customer success—practical prompts, KPIs, and implementation phases to increase coverage and expansion. Ready to accelerate? Book a strategic consultation.

Nina Wilkinson
Oct 7, 202511 min read


Beyond The "Could Have Been An Email": Mastering Your CS Team Meetings
Transform your CS team meetings from dreaded calendar blocks to high-impact sessions. Complete guide with agendas, best practices, and proven strategies for early-stage SaaS teams.

Nina Wilkinson
Sep 23, 202510 min read
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