Dreamforce @ 20 - Marc, mayhem, memories and me

Stuart Lauchlan Profile picture for user slauchlan September 20, 2022
From the first Dreamforce keynote in a hotel ballroom to this week’s return to form, there have been a lot of miles walked around the Moscone Center. Welcome home, Ohana!


It’s 2003 in the ballroom of the Westin St Francis hotel in Union Square, San Francisco, day one of a new tech conference called Dreamforce. There’s just over a thousand of us in attendance for what will be a busy week - I mean, there are 52 presentations on offer!

The event kicks off with Salesforce CEO Marc Benioff riding in to the keynote on a Segway - essentially compulsory behavior for CEOs back in those simpler times - narrowly missing my languidly outstretched foot in the aisle as he does so.

Flash forward to 2022 and here we are again for Dreamforce @ 20. The St Francis has been replaced as the hub by the city’s sprawling Moscone Center, with many other hotels acting as overspill locations. The attendee numbers are pitched at 40,000 Trailblazers this year, those 52 presentations are now north of a thousand sessions, while Howard Street has been converted into the Dreamforce National Park.


It’s a return to form for the gathering after COVID disrupted proceedings and perhaps a welcome sign of normality, if normality is a term that can actually be used to describe a typical Dreamforce. Mayhem is a word a San Francisco taxi driver once used to describe Dreamforce week to me. If so, it’s a very good mayhem - and very lucrative for the taxi driver business I might add!

In my 32 years in this game, I’ve been to an awful lot of tech trade conferences. Many of these were on enormous scale, such as Computer Associates CA World or the various incarnations across the decades of Oracle’s events. I’ve even endured  Germany’s CeBIT - although only the once, you understand! 

Parker goes back to the future

The first user conference that sticks out in my mind is actually the very first one I ever attended, in Atlanta for the then newly-formed D&B Software.

One reason I recall it was due to being struck by the vision of CEO John Imlay, a man whose fondness for dressing up in a a variety of fancy dress costumes to oversee proceedings now looks like a precursor to Salesforce co-founder and CTO Parker Harris’ appearances at Dreamforce in some novelty guise or another. (Sadly now a memory of Dreamforces past…)

Thinking back though, the other reason I recall that D&B event was Imlay telling me how he didn’t want to just put on any old trade show. He wanted his customers to, as he put it, “Have fun, meet their peers and get more out of it than just a sales pitch”. 

That was 32 years ago, but when I try to explain Dreamforce to ‘civilians’ not in the tech sector, that might be as good a starting point as any.

Of course, it is a sales event - no-one is pretending otherwise and nor should they. Benioff told me once that it was the most important sales/prospect gathering of the year, hence all the effort that goes on in  ‘road-testing’ the keynote with customers.

Nothing’s changed on that front. Even with the pandemic-enforced shift to remote business meetings, you can’t beat a face-to-face conversation, whether scheduled in a meeting room or spontaneously taking place in the corridors of the Moscone. And that’s before we factor in the many, many beer busts and wine-tasting receptions that block out attendees social calendars this week.

Real-world meetings also come into play in terms of access to customers. As a customer event from a customer company we should perhaps expect this, but it remains impressive that Dreamforce enables so much customer engagement. As we continually preach at diginomica, any vendor’s best testimony comes in the words of their customers. It’s hardwired Dreamforce DNA.

Thinking back to that first event, something that I’m reminded of is that if I was standing alone, Benioff would introduce me to yet another customer and another and another. I confess from the safe distance of two decades on that at one point I ended up taking myself away to an outside Starbucks so that I could just get on with writing some of this bounty up. What a nice problem to have for a tech conference, I can assure you.

The business of business

But Dreamforce now is so much more than just a sales event. It’s a festival. It’s a family reunion. It’s a Happening! It’s about cloud computing and CRM and AI and all the necessary elements of the technology agenda, but it’s also about philanthropy and diversity and sustainability and leadership. It’s about learning from the rest of the Salesforce Ohana community as well as from famous names from politics, business and entertainment.

Business is the greatest platform for change, insists Benioff. It’s a mantra we’ll hear in some form or another many times over the coming days. It’s also a philosophy that’s been a foundational part of the Salesforce corporate model from the very start in the form of the company’s 1/1/1 pledge, again something we’ll hear about this week.

It’s important to get the balance right, of course. ‘Too woke’ is a cheap and lazy charge to lay, but it’s one that I’ve heard some of my analyst colleagues level against Dreamforce in recent years. To which my response is simple - this isn’t the event for you and that’s a great pity for you…and for the rest of us. If setting out to do the right thing can’t sit easily alongside today’s tech industry pitching its wares, then the sector - and some of its more grizzled commentators - has an unfortunately long way to travel.

Fortunately such voices remain in the minority. 

Changed days indeed

Of course, things have changed over the decades. Apart of the sheer size and scope of the event, there are other aspects that have evolved. Keynotes are built far more around a managerial shared profile these days. We saw this when Keith Block was co-CEO and we’ll undoubtedly see it this year with Bret Taylor now in the same role. While it’s tempting to resort to the tired cliché of Benioff as the ringmaster at the center stage of the circus, today it’s a far wider cast of talent on show and that’s all to the good. (But I do still miss Parker and his costumes…)

Presentation remains slick as befits the most important gig of the year. I do, of course, yearn back slightly to the simpler days of coming into the keynote and finding a pair of comedy clockwork false teeth on every seat to promote the launch of Chatter. Or the time I wandered in with a senior PR person, possibly somewhat jaded from the night before, to see surfboards all over the stage. ‘This’ll be The Beach Boys then,’ I said, making the inevitable connection between the launch of Wave and the imminent prospect of us all (noisily) surfin’ USA at 9am. ‘You’ve done too many of these,’ was the arch reply.

Too many? Nah, not yet. 


That said, I was asked this week what my main memories of Dreamforce are, from the first ballroom experience to this year’s ‘family reunion’. It’s a good question and there are too many anecdotes to choose from. (Just between us, diginomica itself owes some seeds of its origins to a late night conversation in a Dreamforce bar, but that’s a whole other story for another time…)

But a few come to mind when I think about.

A walk in the park

The first was this article, when an unscheduled opportunity arose to stroll around the Dreamforce Park with CEO Benioff and I got a real-time insight into what the event was like from his perspective. It was an unexpected chance and one that nearly had me thrown out by security guards who weren’t in on the fact that I’d been invited backstage, but the ensuing conversation was one of the most interesting and enjoyable of the many I’ve had with Benioff over the decades. Indeed, this remains my favorite piece of Dreamforce content.

But there are two other memories that seem to me to be ‘very Dreamforce’,, starting with the tragic tale of poor Bernard.

Forced to be out-marketed

Who’s Bernard? Well may you ask.

It was the year that Microsoft attempted to turn the tables on Salesforce and took out advertising spaces all around the Moscone Center, telling the story of Bernard, who had turned to Microsoft CRM after being ‘forced’ - geddit? - into a situation he didn’t like by his previous supplier - guess who?

It was, I thought, sauce for the goose. This was exactly the kind of guerilla protest marketing that the young pretender Salesforce did to CRM industry leader Siebel in its early days. The difference was Siebel didn’t have the marketing guile of Benioff’s Salesforce at its disposal to fight back. (Perhaps in an alternative reality it did? What would the tech landscape look like now if it had?)

Anyway, back to poor Bernard. So it was that the next morning’s keynote began with Benioff lamenting the plight of his former customer and wishing that somehow he could make things better for him and bring him back into the fold. As the crowd obediently cheered for Bernard, onto the stage wanders our erstwhile hero himself, in reality not so much a Microsoft user, more a stock image male model, tracked down and flown in by Salesforce overnight to make a repentant return to the Ohana. As a coup de théâtre, it was seamlessly done and a genuine surprise. I’d struggle to think who else could have carried it off.

My final choice is a ‘fireside chat’ session that I still have problems processing. I think of it as ‘Dreamforce overload’. It was the year that President Bill Clinton was due to have the said ‘fireside chat’ with Benioff, but was badly held up in traffic getting to the venue. (Must have been a big conference in town?) What to do with a room full of security-checked attendees? Well, what would any of us do other than phone up Stevie Wonder and get him to come and chat freeform with the Salesforce CEO until Mr President cleared the traffic?

For that particular year that was the point it was too much for me - in a good way. The (positive) mayhem of the previous few days was quite enough without this surreal experience to top it off. I went for a beer, then went to the airport to go home, pausing only to phone a friend to try to explain what had just gone down. She didn’t believe me. But it was a very, very Dreamforce moment.

So, happy anniversary, Dreamforce. We’ve all come a very long way since that St Francis ballroom all those years ago.

Welcome home, Ohana! Now, let’s get started! 

For more diginomica stories from Dreamforce 2022, visit our dedicated Dreamforce event hub

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