Hello, I'm
Simon Cooper
Customer success leader with 10+ years of experience scaling strategic CS functions across startups and enterprises, including Salesforce, Dataiku, and high-growth SaaS businesses.
About Me
I’ve spent over 15 years working in B2B SaaS, starting out as a training manager before moving into account management and eventually into Customer Success leadership. Along the way, I’ve worked with a range of companies, from global giants like Salesforce to late-stage scale-ups like Dataiku and Skai, and even as the UK’s first hire for a Series A startup, Affinio.My roles have taken me around the world, from San Francisco to Singapore, Tel Aviv to Tokyo, and almost everywhere in between across Europe. But what’s always kept me engaged is the work itself: digging into how customers operate, understanding their business in detail, and building lasting relationships that deliver real value on both sides.Lately, I’ve been especially focused on the role AI is starting to play in reshaping the CS discipline. It’s an exciting time, where many of the workflows we’ve relied on are being reimagined, and that opens up new opportunities to lead, not just support, change inside SaaS businesses.
What I Do
I work at the intersection of Customer Success strategy and AI enablement, helping SaaS companies align success plans with business value, reduce churn, and scale what works.Through my digital training platform (SF Cooper Ltd), I support early-stage CS teams with frameworks and resources to sharpen their strategic thinking. And through my newsletter (Plain AI), I help business leaders understand how to integrate AI into customer workflows without the hype or technical fog.Whether I’m advising teams, writing, or building tools, my focus is the same: helping Customer Success evolve to meet the next generation of challenges.
SF Cooper Ltd
Founder – CS Enablement & Coaching
I created SF Cooper to share practical CS frameworks and digital training for early-stage SaaS teams. The core of this is the Success Alignment Model; a proven approach combining Value Mapping, Joint Success Planning, and QBR structure.This platform offers downloadable resources, coaching support, and digital content built from years of hands-on leadership experience.
Plain AI
Writer & Publisher – Plain AI Newsletter
Plain AI is my weekly newsletter helping business leaders make sense of artificial intelligence. I break down how GenAI, agentic systems, and automation are reshaping SaaS, customer success, and operations, without the hype.
Enterprise CS Leadership
I’ve led international portfolios of up to $7.4M ARR, managed CS teams across EMEA, and built value-led strategies for brands like Aviva, Unilever, Amazon, BBC, and Barclays. My work consistently drives retention, expansion, and clarity around customer impact.
Featured Content & Projects
Below is a curated selection of some of my recent projects.These have been both intriguing to learn about and helpful in developing practical skills.
Audio CV
Listen to my AI-curated CV summary, created with NotebookLM.
Best of Plain AI
These are my top performing articles:
I've also created a short course for using AI in the workplace.
Let's Connect
I’m currently exploring full-time CS leadership opportunities where I can bring this strategic and AI-informed perspective to a scaling SaaS or AI-first team.Feel free to reach out for conversations, collaborations, or requests for speaking, writing, or consulting.
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