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. Whether they’re building from scratch or scaling what they already have, the need is the same.
After nearly a decade at Darktrace, joining at ~$5M ARR and helping scale to nearly $1B, I’d built, broken, and rebuilt enough to know exactly what works in post-sales and what doesn’t. 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. Everything undefined, the team small, 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. Most companies at that stage can’t justify (or don’t need) a full-time VP of CS. They need the thinking, the frameworks, and the coaching, not another expensive seat at the leadership table.
That’s why I built Upside. I work with B2B SaaS companies at both stages: building from scratch and scaling what exists. Either way, you get VP-level guidance without the cost or risk of a senior hire.
No pitch, just a conversation.