
Leadership
Losing a deal... and a job
12/11/25, 00:00
Who is it for?
CEOs, founders, CROs, and senior revenue leaders managing commercial teams and decision-making under uncertainty.
When to use?
When you need an experienced second pair of eyes on commercial decisions, planning, and accountability.
That’s truly wonderful, mazal tov to all of you!
That’s truly wonderful, mazal tov to all of you!
From: Ben Miller <ben@millergrowth.co> Sent: 10 November 2025 10:41 To: John Lazar <john@lazar.tech> Subject: RE: Ben's blog: Losing a deal... and a job
Thanks John. I am really well. We just became grandparents!
On Mon, 10 Nov 2025 at 09:32, John Lazar <john@lazar.tech<mailto:john@lazar.tech>> wrote: Good post.
Hope all is well.
From: Ben Miller <ben@millergrowth.co<mailto:ben@millergrowth.co>> Sent: 09 November 2025 22:30 To: John Lazar <john@lazar.tech<mailto:john@lazar.tech>> Subject: Ben's blog: Losing a deal... and a job
John
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.