Retain, Upsell, Repeat: Maham on Scaling Customer Success in a Remote-First Team

In this episode, we sit down with Maham, RepStack’s Director of Customer Success, to unpack how a tiny internal team became an Inc. 5000 company—without losing the culture that started it all.Maham shares the evolution from early roadshows to today’s Repcamps, how Customer Success scales across 150+ client accounts, what “allowing churn” means, and why her team treats retention and upsells like a sport. We also dive into leadership, switching from Athar → Azhar as exec sponsor, returning from maternity while leveling up, and practical advice for working moms and ambitious candidates.What you’ll learnThe rituals that protect culture as a company scalesA director’s daily operating system (standups, temperature checks, placements)How to coach clients so hires produce outcomes, not just tasksThe mindset for retention, upsells, and buyoutsReal talk on remote work, support systems, and leading with empathyTimestamps0:00 Intro — Who is Maham & her RepStack start (2021) 2:25 What changed from the 7-person team to Inc. 5000 5:18 Culture that stuck: roadshows → Repcamps, learning as a core value 7:45 Role breakdown: Director of Customer Success (day start to end) 11:20 “Temperature checks,” EODs, and how we read account health 14:02 Coaching clients: from hiring a person to producing outcomes 17:15 Taking on challenging accounts & why that accelerated growth 20:10 Moving from CSM → Director: owning vision and numbers 23:30 Switching exec sponsors: working with Athar vs. Azhar 26:55 Big goals vs. stretch goals — the “allow” language for churn 29:18 Why Customer Success is the most rewarding seat at RepStack 32:10 Remote realities: proactive service, 24/7 client moments 34:22 Maternity & momentum — advice for working moms (build support!) 38:05 Hiring philosophy: problem-solvers over problem-creators 41:00 How to thrive at RepStack: be uncomfortable, be coachable, be proactive 44:10 Closing thoughts — changing lives (and generations) through work