Losing a deal... and a job

I lost the biggest deal of my career on Christmas Eve, and subsequently lost my job.

This set me on a path through RevOps to CCO to adviser, and the most satisfying period of my career.

December 2016. I was running the international sales team, everything but the US.

We had grown strongly for several years from 5m to nearer 50m.

We had a huge deal in New Zealand (yes, there was a huge deal there!). I was absolutely convinced that we had this sewn up. It was the backbone of the quarter and I made the double mistake of telling the CEO it was a done deal.

❌ It clearly wasn’t a done deal!

❌ The new CEO was a one-strike-and-you’re-out guy

A couple of months later I was “demoted” – at least that’s how I saw it at the time – to RevOps.

I had been there 20 years, and it was time to find a new path. It took 18 months of hard networking, with two clear rules:

1️⃣ Two coffees every single day

2️⃣ Every meeting, get two more introductions

18 months later I made myself into start-up world, 2.5 years after that I was Chief Commercial Officer at a fast-growing scale-up, and less than a year later, unemployed again as Covid took its heavy toll.

Reaching out, through the network I had worked so hard to build, looking for a new CRO role, I discovered a lot of people needing support and advice on sales and GTM development so figured I would give it a try.

Never has serendipity been so kind. All the mistakes I learnt, many of them encapsulated in that deal, are now part of day-to-day coaching:

🤝 Great relationships do not mean great deals.

🙈 There are people in the account you don’t know, championing your competition.

📋 If the mandated requirements do not clearly position you at the top of the list, you are vulnerable.

🟦 No matter how much people want to buy from innovative companies, you-don’t-get-sacked-for-buying-IBM lives on*

I also learned that every door that closes opens another.

Today I work with incredible founders, sales leaders and go to market professionals. I have the privilege of engaging with start-ups, scale ups and PE backed companies.

And most of all, I have found something I truly love doing.