Gagandeep Singh
- Specialism: Fractional Go-to-Market leader and Chief Marketing Officer for high growth Cybersecurity and SaaS scale-ups often PE or VC backed.
- Track Record: F-Secure, Blancco, Withsecure, Handshake, EY, MWR Infosecurity.
- Offer: Fractional CMO services for Cybersecurity and B2B SaaS including: GTM Assessment and Growth Roadmaps, Marketing Strategy and Go-to-Market alignment; Fractional CMO Partnership; Demand Generation Systems; Category Positioning and Differentiation; Board-Ready Growth Planning; PE/VC Marketing Alignment.
- Gagandeep says: “I help ambitious cybersecurity and SaaS companies break out of the pack – aligning GTM, winning more of the right deals, and creating category leaders.”
- Try me: linkedin.com
After years of working in senior marketing roles, I’d seen the highs and lows: big wins, tough boardrooms, restructures, redundancies. Each time, I delivered results that moved the needle – bigger pipelines, stronger positioning, accelerated growth. And yet, like many others, I found myself out of a role not because of performance, but because of circumstance. I reached a point where I realised I didn’t want my future to depend on someone else’s restructure or budget cut. I wanted to work for the one person who wouldn’t make me redundant: me.
I got started by setting up Boostra as a “plan B” while exploring what might be next. I built a simple online presence and started sharing what I knew best: how to fix growth problems. Very quickly, old contacts reached out. One asked if I could help with their go-to-market. I replied, half-joking: “You don’t need to hire another full-time CMO, you need me.” That was my first fractional engagement, and it proved the model.
My first success was with that client, who was under huge investor pressure to grow but lacked marketing leadership. I came in two days a week, reset their strategy, aligned their sales and marketing, and gave the board a plan they could finally believe in. They saw a step-change in pipeline within months. For me, it was validation: this wasn’t a stop-gap. This was the future.
Along the way, I’ve learned three key lessons:
Trust is the currency. CEOs and boards need to know you’re in the fight with them. Doing what you say you’ll do, when you say you’ll do it, is everything.
Balance is key. Clients value flexibility, but it’s vital to be clear you work across multiple businesses, and that they all benefit from that cross-pollination of ideas.
Keep showing up. Sharing insights, staying visible, cultivating your network — these keep the pipeline alive.
It’s working for me now because, even though it’s still early days, I’ve built a small portfolio that gives me more security and balance than any permanent role ever did. I’m home more, present more, and working with leaders who value outcomes, not politics.
Looking ahead, my goal is longevity: fewer, deeper partnerships where I can help companies not just grow, but become true category leaders. Alongside that, I want to remain an active student and learn from high-performing peers, networks, and communities to stay ahead of the curve.