^{Thanks for being patient.}

The Boston Business Journal beat me to the punch yesterday, but in case you missed it or hit the pay wall, today I will be sharing more about the idea we are pursuing. Thank you for your patience and support. Let’s get into it!

When you ask CRO’s and VP’s of Sales that had big wins and losses throughout their careers, they will tell you that the difference is usually a combination of both timing and product market fit. I’ve personally experienced both and 100% agree. Get it wrong and your dead, no matter how good you are. Get it right or at least kinda right, and you have a chance.

With that in mind, I asked myself… what are the best sellers organically doing today to win more deals?

First principles: Despite market conditions, the best companies and sellers are finding new and innovative ways to win.

Where is that innovation taking place? What are some seeing that others are missing? In short, what is cutting edge today that will be considered best practice in 3-5 years?

So I searched, I interviewed, I listened, and I reflected on my own experiences.

Have you heard of a Digital Sales Room? Me neither. I had never used one.

I was familiar with the concept of a “deal room” but only recently discovered that G2, Forbes, Gartner, and Forrester had coined the term “digital sales room” or “DSR” for the category.

DSR’s are basically a custom shared space for a prospective customer and a seller to organize what otherwise would be buried in emails. Collateral, questionnaires, case studies, pricing, business cases, proposals, onboarding plans, etc.

The space has serious momentum and while that is exciting, it also has major criticisms and arguably more skeptics than fans.

The good: It’s much more than a project management tool. For sellers a DSR allows them to elevate the experience they deliver to customers, helping them edge out the competition. I’ve always been a big believer that the pre-sales experience is a try-out, a subconscious predictor of what is to come for the buyer if they select you. Does the organization, skill, and experience of the seller give them the impression that this company will be able to deliver on the value they promise? When all else is equal, this matters, a lot. 

The bad: What buyer wants to sign in to a third party app that they do not use, just to potentially buy something? Put yourself in their shoes. Would you want to sign into a foreign app to engage with a sales person? Knowing a primary goal of the app is to gather more information about them as buyers. Who wants to use something that tracks the time you are spending in a case study or your specific click path? Some, but definitely not all. Also, Sellers look at these tools as clunky and just another thing that could slow down a deal. In short, the biggest issue with Digital Sales Rooms is the adoption curve for both sellers and buyers alike.

Cool concept, but deeply flawed IMO. No one has it right.

I pressed myself to reflect on what I observed as CRO and to revisit conversations I had with other VP’s of Sales and CS over the last year or two.

What are the best doing today thats unique, differentiated, and giving them an edge? What was organically happening out there? That was also ahead of the curve?

It hit me. They are using Slack and Microsoft Teams to connect with prospects and customers. It is still relatively new, but the innovators are far along with this concept. The “channel connector” or “Slack Connector” lets two companies connect a specific channel over Slack while keeping the rest of the slack environment private. For companies that are using Slack, it is one of the apps that is open all day, for almost every department. It is where they spend the most time. It is convenient. They like it.

The best sellers are using Slack to connect to their prospects and customers, creating their own version of digital sales room.

I saw this first hand in my prior role as CRO. I then had countless conversations validating this with peers. But it wasn’t every time or every seller. It was the top performers finding new and creative ways to win.

So I polled Linkedin.

38% actively use slack or teams in their sales motion with prospects and customers (not just internally).

22% sometimes use slack or teams in their sales motion (not just internally).

40% said they don’t use slack or teams in their sales motion

So how and when does this slack tactic play out? How are sellers getting prospects to connect over slack? Some invite them to a Slack channel at the demo stage and others wait until the deal is signed. The most common stage however is to organize communications when a deal progresses to the proof of concept or product trial stage.

Similar to a digital sales room, it becomes a central hub for the deal. Handling everything from general Q&A, scoping and tracking of evaluation criteria, creating mutual action plans, proposing and collaborating on business cases and pricing proposals, and as much additional sophistication that may exist in your sales process, it helps to keep it all moving along.

Major unlock: When a deal is closed won over Slack, the channel shifts to the customer success handoff and then quickly becomes the onboarding channel and ultimately it evolves into an ongoing support, upsell, and renewal channel. When Slack is used as a Digital Sales Room, it becomes the preferred method of communication for customers.

Why? It’s more casual than email, and more convenient than a zoom meeting. It’s easy for both parties bringing them closer together. The old saying was “if you aren’t on a text basis with a champion they aren’t a champion”. I think that is evolving to “if you aren’t on a text OR slack basis with a champion they aren’t a champion”.

It’s exactly where customers and sellers both want to be, the only problem? It’s generic, super basic, manual, time consuming, and not nearly as powerful or automated as a digital sales room. It’s not repeatable, it’s not tracked in the CRM, it’s a one off, every time.

Winrate is the first Slack native Digital Sales Room, bringing the full power of the DSR to the place people are already working. This includes connecting to Microsoft Teams, so that Slack native companies do not need to buy separate licenses just to communicate with customers using Microsoft.

So let’s look into the future. If you asked me to revisit that poll in 5 years? How many sellers and revenue teams will be using Slack or Teams to communicate with customers? I’d predict 90%+ yes, 5% sometimes, and 5% no.

The Digital Sales Room is really about delivering a world class experience. 

It will have it’s day in the sun, and that day will be in Slack and Microsoft teams. Not in some 3rd party app. Those will go extinct.

What Podcasts I’m listening to? 🎙️

Revenue Builders - John McMahon is one of the GOAT’s in CRO land. If you’ve read the Qualified Sales Leader, you will love this pod.

Grit - There isn’t a broader collection of top tier guests focused on the most interesting people in business.

Topline - The ultimate startup pod. I would recommend it to anyone in GTM trying to learn, grow, and find a sense of community in your headphones.

🔊 Spotify Playlist of the Week