I built Upside because the companies that need the most help with post-sales are exactly the ones that can't justify a full-time VP of CS.
I spent a decade at a cybersecurity scale-up that went from ~$5M to nearly $1B ARR. I joined early and worked my way up to VP of Customer Success, responsible for renewals and expansion across ~$100M ARR and ~4,000 EMEA customers.
When I arrived, there was no Customer Success function. No team, no playbooks, no commercial ownership of anything that happened after a customer signed. I built it all from scratch: a team of 50, every manager and second-line leader developed internally through promotions rather than external hires. I designed the renewal and expansion motions, built the coverage models, and turned a reactive support function into a revenue-owning post-sales engine.
The results were public: net revenue retention improved from ~98% to ~107%, gross churn fell from over 8% to ~6%, and expansion ARR grew by ~120% over two years. I consistently overperformed against renewal and expansion targets across three consecutive years.
After the company went through its IPO and a $5.3bn PE buyout, I left. The obvious next step was another VP role at a later-stage company. But that didn't excite me.
What I kept coming back to was the early days. When everything was undefined, the team was small, and every decision mattered. That zero-to-one phase is where I do my best work, and it's where the right guidance makes the biggest difference.
That's Upside. I work with B2B SaaS founders who are at the stage where that company was when I started building. I give them the strategic layer that took me years to develop, without the cost or risk of a senior hire.
No pitch, just a conversation.