Six tips on enterprise sales

This is the second blog in our B2B Go-To-Market series. You can read our first article to learn more about B2B lead generation best practices.

As an early-stage company, approaching the enterprise can seem like a daunting and overwhelming prospect. The sales cycles are longer, more complicated and involve many more stakeholders.

So how do you win over the enterprise? How do startups sell in this segment? And how can you shorten the sales cycle?

Our panel of sales leaders – Brogan Taylor, VP of Enterprise and Strategic Sales at Freshworks, David Mackay, former Global VP of Enterprise Sales at Hootsuite and Senior Sales Director at Adobe, and Brian O’Reilly, VP of Sales, Customer Success and Operations at Melio – share their six top tips on enterprise sales.

Tip 1: Build a mutual action plan

The biggest challenge in the enterprise segment is that the sales processes are getting way more complicated. There are far more steps with lots of red tape, intensive data and security reviews, cybersecurity compliance and so on. To navigate and shorten those sales processes, you need a really consistent sales methodology.

For David Mackay, you should also go one level further: “We don’t call it a sales methodology anymore. We call it a customer communication framework. And it’s the overall method for how we’re engaging with customers and communicating how we’re helping them drive their key business imperatives and exposing the value attached to those things. 

“On a more tactical basis, there are some of the basics like having a joint execution plan with the customer. This is an agreement outlining the steps you’ll go through to get through the end of the process and the dates and timing. Just that simple tool will shorten the sales process significantly.” 

Tip 2: Button up on process

To be successful in enterprise sales, Brian O’Reilly stresses the importance of “very, very clear sales processes and a very, very clear exit and entry criteria as you go from each stage of the sales cycle to really understand why the prospect is buying now.” 

Brogan Taylor agrees – “I tell our teams we have three jobs right now, pipeline, process and partners, as we move into channels.” One thing that has worked really well for him and his team is working hand-in-hand with the sales engineering teams, on the process, every step of the way. 

Tip 3: Approach ‘whales’ with caution

With enterprise sales, timing is everything and so is being aware of your business’ age and stage.

“My commitment to my CEO should be that we’re not going to bring a whale into the boat that’s going to sink our business,” remarks Taylor. “Our product roadmap is never for hire. We need to understand our maturity and where we’re at, and sell to customers that fit that reality. 

“That’s where I’ve seen people go wrong; they try to bring in the whale, they do all custom development for the big fish, and it sinks the company just for that one customer.”

Tip 4: Actually measure the sales cycle

Many businesses actually don’t measure their sales cycle length nor do it on a ‘per rep’ basis, observes O’Reilly. And this is one of the most basic things you can do. 

“You can study which reps have a shorter sales cycle, a longer sales cycle, and start studying some of the patterns. At a previous startup – a cloud-based translation technology and language services that sold to the enterprise – we started doing this and we found two things: 

  1. Multi-threading – i.e. the more people you have engaged in the sales cycle, the faster it moves
  2. ‘Why now?’ was one of the key qualification questions that we had. So why are they buying now? Why didn’t they buy six months ago and why not six months from now? The reps that had the most comprehensive understanding about exactly why the prospect was buying now were the deals that moved the fastest also.”

Tip 5: Understand the C-level motivation

Learn what’s driving the initiative to buy, Taylor remarks. “The buyer might say something like, well the current customer support solution is old and we need to update it. That’s not the real reason. When you associate yourself with the C-level goals, and when I hear something like ‘if we don’t open up chat to capture millennial market share, we’re going to get beat by IKEA and Wayfair’, then I know that’s the budget train that’s going to leave the station.

“It isn’t that the buyer needs a new CX solution, right? Dig into the problem, but go up one level higher. That gives better predictability because business imperatives get funded.” 

Tip 6: Ensure your sponsor is a champion

Our panel emphasizes the importance of having an exact sponsor on the customer side and keeping them engaged. “Ensure you have some direct access to that exact sponsor and, secondly, that you have a champion. You need to be very clear on who your champion is in the organization,” adds O’Reilly. 

They also suggest engaging multiple sponsors. Given that sales cycles are longer, and that people on the customer side resign or move positions during that time, you want to ensure that you have considered how to navigate those transitions so that you don’t find yourself, 12 months down the line, starting from scratch.

This is the second blog in our B2B Go-To-Market series. Our next article looks at building teams and how to hire the right talent. You can visit RTP’s News and Views to read all the articles in the series.