This deal was by far the hardest fought of my career to date...and up to now I have never been able to tell the story. For context, we were a Pre-Series A content marketing SaaS company and I was the very first employee they hired (had been there for almost two years at this point). Our product was awful and totally taped together but we knew our strengths and had some good connections, so up to this point we'd manage to grow well within SMB and mid-market accounts. I also had a total w@nk3r for a boss at this time who had never sold SaaS but thought he was god's gift.
It all started with being invited to a networking event hosted by an investor which was a meet and greet with some FTSE100 stakeholders and I was presenting for my startup in front of an audience of about 100 people. Smashed the presentation, got a load of leads from it but nothing mind-blowing.
A week later, I get an email from a lady who picked up my card (left it inside the brochures I handed out before the presentation). She works in an innovation role at a major CPG business and was looking for something to show off at an internal event and she thought I could help. Turns out, I could.
Hopped on a call, demoed and talked pricing. A couple days after, she had approval and we need to fly through procurement as the event itself was in 4 days. Ended up dropping my pants to make it happen (so we fell below a discretionary spend threshold) and then managed to scrape our way through security review (we were a very scrappy tech startup so a lot of smoke and mirrors involved in making us look legit) - I then had to actually deliver our tech for this event myself. My aforementioned boss thought the whole thing was a waste of time as it was a cheap deal.
Worked all weekend to get us ready and was up at the crack of dawn both Monday and Tuesday for the event itself to setup hardware and our software. Put my all into it and by some miracle, our tech stood firm for the whole thing. It was such a good opportunity for a really relevant audience w/in the organisation to see our platform in action and I walked away with some new connections.
And then, nothing.
Followed up, tried my connections, tried dropping by the office - tried everything. We were dead in the water and my boss thereafter continually referred to how much of a waste of time the previous deal had been and personally took shots at me for bending over backwards to make it happen.
Eventually (we're talking 6 months later), I ended up running into my original contact again when I was walking to a meeting nearby their office. We got on quite well personally and she said that it was perfect timing as she'd spoken to an internal client about a project that could use our help the day before.
Fast forward a bit and we deliver this second project (no need to go through security/procurement review this time) and we delivered a POC on a brand campaign with one of the CPG's biggest logos that ended up winning a few industry awards. The revenue this time was better but still not top dollar.
But that was the moment where things took off and lo and behold, my boss cut the crap, finally. Briefs came flying in from everywhere and we had more POC projects than we could handle and it all started adding up. For 6 months afterwards, my job became 90% focussed on growing this account - and then it reached a point where they wanted a global MSA with a pricing schedule attached. My boss quit around this time so I was in a position where I reported directly to the CEO who encouraged me to do whatever it took to get the deal done.
Went back and forth for a few months and then bang - we had contracts with every category in this company, in every major market - good personal relationships, successful implementations and an army of internal champions.
That deal precipitated multiple new enterprise contracts for the business (even after I eventually left) and is still by far the biggest deal the company ever closed with the value growing beyond the value stated above still.
Its been the launchpad for them to raise Series-A investment and for me to move into more senior, better paying roles in better companies. I am so proud of it.
It took a lot of bloody-mindedness, graft and most crucially - luck; my contact was at that original event, found my card, emailed me, ran into me on my way to another meeting and turned out to be a total legend.
Never give up.