Why Customer Success is a Continuous Sales Motion with Rav Dhaliwal from Crane Venture Partners

Investor and former customer success leader Rav Dhaliwal shares his secret sauce

In this episode of CCO Secrets, we had the honor of speaking with a customer success leader who has one of the most impressive resumes out there. 

Rav Dhaliwal is an investor and venture partner at Crane Venture Partners. But his path has been one-of-a-kind. He held executive and leadership roles across companies like IBM, Salesforce, Yammer, Zendesk, and Slack, just to name a few.

We spoke with him about his time as the first Slack London employee, how the days of on-premise software live on, and how CS leaders can get a seat at the table. 

Meet Rav Dhaliwal

In his current role at Crane, a European-focused VC fund, Rav spends his time prospecting potential investments and working with their portfolio on all manner of go-to-market activities. 

But his career thus far has been almost entirely customer-focused. One could argue he was always in “customer success” even when his role was something in IT or software engineering. 

He once had an infrastructure/UX role where a large part of his time was spent doing all the support work — fixing things in the database, troubleshooting questions, etc. 

“And then probably about 12-13 years ago, I started my first ‘CS’ role, working with customers to help them realize the value of the solution they bought,” he said. “But helping them to realize that value hopefully quicker than if we'd left them to their own devices. So it’s all been broadly customer and sales-focused work, but just pulling slightly different levers.”

Rav went on to be the first employee for Slack in London. This was an interesting journey because their CS function didn’t technically exist … yet. 

“There was a kind of understanding that we needed to think through how we work with customers. So a lot of what I was doing was figuring out if we build customer success, what should it be focused on? What value should it be delivering?

“And through a combination of sitting in on deals, being part of deals, and then speaking to lots of customers, we really hit on the idea that actually what we're trying to solve is less of a technology problem. It's more of a behavioral change management problem. It's a digital adoption problem. So that really helped us build the foundation of the team and hire the right kinds of skills.” 

The lack of executive representation

When it comes to a lack of representation of CS at the board level, Rav says there isn’t just one answer. But a big part of it has to do with how we organize as companies. 

“If you look at how a contemporary SaaS startup is organized, especially around sales operations, it's virtually identical to how it was 25 to 30 years ago when we sold on-premise software.”

With on-prem, you were perpetually licensing the customer — they owned it forever — and there was also a big capital cost; therefore the switching cost was very high. 

“We've essentially taken that production line, and we've moved it into a subscription-based world where we distribute the software through the cloud. And we license it completely differently. People rent the software now. But we're still organized that way,” he said.

Put another way, we still think in pre-sales and post-sales terms. And that’s an extension from how software companies were built 20 to 30 years ago. But today, we’re actually in a continuous sales motion. 

“And so we want to make sure that the customer sees value from the solution really, really quickly, and that we get them to use the system and the software as proficiently as possible — i.e. make it "sticky" so we earn the right to come back and talk to them about more revenue.”

This orthodox production line is part of why we don’t see as much representation of customer success at the board level. Because everyone thinks the job finishes at contract signature, he said. 

“And really the job starts at contract signature. I was in a board meeting the other day, and the way I explained it was, ‘ACV is the lifeblood of the company — it builds the company, but NRR sustains it,” Rav said. “So without net revenue retention, we can't be a big company. Because we will eventually max out who we can sell to. So that, I think, is fundamentally a structural, historical problem.”

Getting a seat at the table 

Rav hypothesizes that CS representation can increase if more CS teams take on a net retention goal and a mindset shift around the role itself. 

“I think it's kind of a shortcut for explaining, ‘we make this investment in CS, and we're showing what we're adding back to the business.’ I'm always saying, as a CS professional, your job is really hard because you've got two customers. You've got the people who bought the software and everyone else internally, and you're constantly having to try and manage both.”

The easiest way to manage this internal audience is to say, “we do X, and X results in Y, and Y is important to us as a company,” he said. And while this approach is advantageous, there must also be a change in mindset. 

“People who have the aspiration to sit in that board meeting and be at that level would have to really accept, ‘I run a continuous sales motion. That's what I'm doing. I'm pulling more of a product and value lever than an overtly commercial one, but that's the reason why I'm here.’ And I think a combination of those two things, I would imagine, would lead more people to have a seat at that table.”