Death of a “Top-down” Salesman

Jake chucked his BMW keys to the valet and strolled into the steakhouse.

He arrived early for his dinner reservation to peruse the wine list and find the perfect pairing for the porterhouse he knew his prospect, Paul, would order. He wanted to project “power” and “confidence.” Jake needed this deal to qualify for President’s Club and that trip to Cabo. He was willing to go the extra mile to close this baby out before the end of the quarter. 

He texted Paul, his decision-maker. It was 7:05 p.m. and Paul was now late. Jake stared at the iPhone screen hoping the three dots in the speech bubble would appear. 


Jake hated himself for feeling so desperate. He put his phone, face-down, next to his plate. Suddenly, it buzzed. The VP was caught up with some stuff and couldn’t make it. 

Couldn’t make it?!? After 9 months of demos and ongoing negotiations this was supposed to be a done deal.

Jake tried calling him. It went straight to voicemail.

He wasn’t going to close this deal or make it anywhere near Cabo. He was starting to lose his appetite for this $70 now in-expensable steak. 

Tomorrow was going to be a frigid day of cold-calling. 

“Jakes” all over the world are losing deals. Why? Enterprise software purchases are no longer fueled by schmoozing. In fact, VP’s and C-Level executives have very little say in the buying process.

The death of top-down Sales is driven by the consumerization of B2B software. Also, known as “Bottoms Up SaaS” or “Self-Serve.” It’s easier to understand this if we examine what Jeff Lawson, CEO, and Founder of Twilio, refers to as three distinct eras of enterprise software.

The First Era 

Or theSteak Dinnerera was marked by massive, multi-year, multi-million dollar initiatives approved by C-Level executives. Like a $20 million ERP system purchased by a CIO. 

If enterprise software was a hot nightclub, Jakes were the swole bouncers. Prospects would line up outside in the cold and answer a series of questions before ever getting a chance to peep inside only to be shocked by the price of admission.

End-users would have no say in picking a solution and would have to take the salesperson’s word for it.  After countless on-site meetings, steak dinners, and rounds of golf, the executives who signed the contract would switch roles or leave companies and the project would never get implemented aka it would “die on the vine.”

The Second Era 

This was the “Talk to Sales” era. It had lots of on-site meetings, steak dinners and rounds of golf, but multi-year evaluations shrank to 12 months or less. Customers could get up-and-running with a new solution much faster since they didn’t have to run the software. 

VP’s and C-level executives were still the decision makers, but the number of stakeholders influencing the selection process grew exponentially. Jakes were still the bouncers, though a bit scrawnier, and in most cases you still wouldn’t know the price of admission prior to entering. 

If you were an end-user, you couldn’t test the SaaS solution before talking to an Account Executive. You were subjected to a discovery call, a demo, and countless slides that touted all of the other great customers they had closed. 

You also had to place a lot of trust in your Account Executive. And, that’s if you were lucky. If you couldn’t commit to a minimum spend, salespeople wouldn’t bother speaking to you. High-rollers only. If you didn’t fit the bill, Jake would direct you to the sketchier nightclub across the street.” 

The Third Era 

Or the Revenge of the Devsera is the age of “Bottoms-Up” Sales.  Companies like Twilio, Stripe, and Plaid enable developers to tinker with building blocks before designing differentiated internal tools that give their teams a competitive edge. 

This era flips the buying process. It liberates builders. No more lining up outside the club. No need to endure a fluffy sales deck. Developers can find answers to their own questions while hacking on a problem at 2:00 a.m. by diving into the docs. They can start a trial with a credit card and see preliminary pricing. In fact, pricing transparency is table stakes. Developers demand to know exactly how much a building block costs before they integrate it into their internal tools. They no longer have to take a salesperson’s words as gospel.

Developers are empowered to source their own tools. After testing multiple solutions they can present their recommendation to executives for budget approval. This is a win-win as it allows executives to focus on different areas of the business and ensures their teams are invested in the successful implementation of the solution.  

Time for Jakes to evolve.

How can modern-day salespeople adapt and thrive in this era? 

  1. Build Momentum

The “Steak Dinner” and “Talk to Sales,” eras were all about delivering a killer demo and selling your prospect on trying your tool. That’s no longer necessary. Most buyer’s will have already tested your solution before reaching out to you. Your job is to build momentum within their organization. 

What does that mean? 

You need to determine if the project they’re working on is a company-wide initiative or a side-project. If it’s the latter, your job is to expand it. That’s one of the main values great salespeople provide in this new bottoms-up world.

Elite Account Executives are still indispensable. Some founders boast about building hyper-growth enterprise software companies without sales teams. They’re either lying or playing semantic games. Case and point —  Atlassian. Their founders famously said, “Whatever you’re going to spend on sales, just put it into the product to make the product better. Anytime a customer needs to talk to a sales person, that’s a bug you have to go fix.” 

They had salespeople. They just called them Enterprise Advocates.

  1. Champion to Hero

Your prospect (aka “champion”) has to solve a problem for their company. Their boss may be pressuring them to build a custom solution. They have to find a tool that checks all of the right boxes, and herd the cats to test it out. Their director may want to use a different tool — the one they used at their previous company or the one they angel invested in.

You have to turn your champion into a hero. 

How do you do that? 

Make it easy for them to sell internally. This doesn’t mean pressuring them to introduce you to the main decision-maker ASAP. It means enabling them to sell and get their teams excited. You may have to build a custom deck for them. You will have to teach them how to frame the benefits of your solution to different stakeholders within their company. You will show them how to navigate their internal buying process.

If you do all this right, they will want to introduce you to other stakeholders and they will have your back when you go to battle with procurement.

  1. Add Real Value

A lot of salespeople add value. The problem is, it’s mostly to their own organization. Real value is more than increasing your average deal size or accelerating deal velocity although those things are nice too. In the new era, most buyers will know just as much — if not more — about the product than the salesperson. Your job is to provide incremental value they can’t get in your docs or on your website. 

Gain a deep understanding of your prospect’s problem and provide guidance on how similar companies have solved those challenges. This includes giving them concrete examples from other success stories. It’s easy to point to a case study on your website, but providing real value means sharing more intimate insights that can only be garnered by being in the trenches with your customers.

Central to adding real value is making your prospect into a partner not just a customer. Ask for their feedback on upcoming feature releases and put them in touch with your product teams or founders. Experimenting with a new pricing model? Schedule calls with a handful of customers and walk them through the new model. Not only will they provide invaluable feedback, they will feel like a part of your team. 

Elite sales reps won’t view this aspect of their job as an additional responsibility. They’ll understand it’s as important as hitting their quarterly number.


COVID may be the nail in the coffin for top-down sales. Whereas salespeople were jilted at restaurants before the pandemic, merely inviting prospects to dinner can offend them. Heck, you can’t even send cupcakes to prospects anymore. Almost no one is at their offices and asking for your prospect’s home address is a risky endeavor.

Software is eating the world and great salespeople help feed the beast. Enterprise software companies like Zoom, Twilio, and Okta still rely on salespeople but in this bottoms-up world, successful reps don’t follow a “Steak Dinner” playbook.

This era favors product-driven companies, and fosters a higher level of mutual respect between buyers and sellers. It also invites a new type of “closer” to take the reins—one who helps their champion become a hero by solving their company’s most pressing challenges. 

No more steak dinners. No more cupcakes. Just partnerships and problems solved.