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Podcast Recap: What Customer Success Can Do To Improve Alignment With Sales

Updated: Jan 31

Hey Customer Success, we’ve got some work to do!

Yes, we’re all fighting the same fight, “Sales <> CS lack alignment” but there are some things that we can do to fix this.

The most qualified person to tell us this is a VC Investor who has a birdseye view on what’s going on. If you’re ready to take a good look in the mirror, Rav Dhaliwal is here to show us how we can push for alignment AND let the rest of the company know what our true value add is!

The details

In this post, we are recapping an episode from the Gain Grow Retain podcast called “Customer success is critical to building a valuable SaaS business” with Rav Dhaliwal, a Venture Partner at Crane.

This is a first for keep the customer, it’s the second time we recap a podcast featuring Rav. As a VC investor, he’s previously given us the inside scoop on what Customer Success means to investors. Something new that I learned about Rav during this episode is that he started in construction and then moved into tech––he’s a self-proclaimed handyman! That’s impressive but also, he’s worked at companies like Yammer, IBM, Salesforce, Microsoft, Zendesk, and Slack (you know, the crème de la crème).

The Gain Grow Retain podcast is also on fire 🔥it’s the third week in a row we recap their episode. Go check them out if you haven’t subscribed yet!

Alright so let’s dive into our takeaways:

  • The assembly line mindset we need to get out of

  • How to stop swimming against the currents of CS <> Sales alignment

  • Present your CS metrics for the company not to the company (example)

The assembly line mindset we need to get out of

When Rav sits down with some later-stage companies, their main focus seems to be “How do I sell this thing/how do I market?” and for early-stage companies, it’s about “I just gotta build this thing and sell it”. Both segments start doubling down on answering these questions/solving those problems and that’s when Rav and his team step in to help them broaden their thinking.

They challenge them by introducing a new case: “not just how do you market the product but how do you grow and retain and how do you create a sustainable revenue model?”. His goal is to shift their mindset so that they start thinking about laying some foundational pieces now that way they’re much stronger and healthier when they’re looking for later funding rounds.

By setting the foundation early on, when Customer Success (CS) is introduced, it doesn’t feel like they’re responsible for driving all customer engagement or creating completely new processes from scratch. If a company started building the foundation early on, CS can then take a look back and start latching onto processes that are already in place. For example, in Product, they’re speaking to customers to get feedback. CS should be thinking of ways to latch on to what they’re already doing and create processes from this.

Here’s the problem…

We’re stuck in the old days.

It goes back to the industrial era if we think about how larger companies have been organized. They worked off of an org chart structure that is designed for high volume manufacturing. They take something that is very complicated, break it down into very small individual uncomplicated components. They then maximize the production of each of those components by having one person work on one component. That person didn’t need to know what the other person is doing, they just need to know what they’re doing.

That organizational structure was designed for efficiency, predictability, and repeatability. We’re in the software business now but we’re still in the same structure. We see this day in and day out. When you walk into an organization, Jeff adds, it feels antiquated when it comes to how departments interact with each other. For example, you have Customer Marketing where it may sit in Marketing but it’s at odds with the premise of Marketing “acquire more customers”.

Shifting the mindset

“When it comes to working with customers, you don’t have any authority, all you have is influence. You can’t make the customer do anything, you can just influence.”

This also applies to CS leaders/practitioner,s you should have this mindset internally too. You may not have authority over Sales or Product but you do have influence. If you actually exercise that muscle and think, “what is this group trying to achieve?” there’s probably more alignment in what they’re trying to achieve and what you’re trying to achieve. If we can all try to understand this, we can all drive influence and everyone wins!

How to stop swimming against the currents of CS <> Sales alignment

In his article “There’s no such thing as post sales”, Rav hits on a few things: the buyer is often not the deployer, alignment between Sales and Success, and CS is not a department, it’s an operating model. Let’s cover the first two.

The buyer is often not the deployer

This is something that occurred to Rav when he was working with different companies that were at different stages of the journey. He realized that you can get huge traction in an SMB and you think “the product is great so let’s start selling to larger enterprises” and all these little problems you didn’t think about, occur. For example, product scale and deployment problems.

So Rav thought, why is this the case? Why does this work well for a 500 person company and then you get to a 10k person it starts to become so much harder? He realized that the likelihood of the right person being exposed to this problem early was small. That’s because in larger companies, the people who are deploying or configuring tend to be further away from the person who bought it. The list of people that a Sales team needs to speak to before the check gets signed is larger than we’re accounting for.

The second part of this issue is that organizations are structured in very rigid ways, it kinda sounds like this “well if my only incentive is hitting a number in a 12-week increment I will not want to introduce anything that will slow the efficiency of that process down”. If we change the incentive structure even slightly, we might start shifting to a longer-term method.

Alignment between Sales & Success

Similarly from a CS standpoint, and Rav notes that this may be controversial, but it always seems to be about outcomes. Rav agrees with them but if you want to influence people internally, that outcome needs to be about revenue. With a customer, you may say “what’s your business outcome, what’s your goal?” inside you have to draw the line between doing that and driving revenue internally.

Present your CS metrics for the company not to the company (example)

Rav wants to challenge us in Customer Success!

One of the things he’s noticed is that there’s too much psychological resistance of being thought of as being a salesperson.

Sales is a hard noble profession, there’s nothing wrong with it!

If you can get Sales and CS to think “Sales is about driving value, not revenue. Revenue is the outcome”, (quote from someone at Hubspot) then you’re in a good place.

It’s the CS professional/leader to explain why they are there/what their role is and it should sound like this: “the reason I am here is not so that the customer likes me or that they take my phone call or have a great relationship-- that’s all a proxy for driving revenue.”

As CS, the way we’re going to drive more revenue is not to do the hard sales, it’s to uncover where we can add more value. The lever we’re pulling is “value” and it’s something that applies to Sales + Success. Otherwise, Rav warns, we’re going to continue going round and round.

Rav has learned this the hard way by failing at this multiple times.

He’s worked at companies where he was the 1st or 3rd person hired so he had to close deals too. At that time, he realized Sales is a really hard job and yet is really pressurized. Sales has a leading indication while Success has a lagging indicator so how do you square that circle to realize it’s a continuous motion? It’s not a “sell and move on” its “sell and sell again”.

How can we start demonstrating our value add as CS

There is no true answer but the one thing CS teams can start doing now is presenting the numbers in a way that actually resonates with the decision-makers, chief execs, or the board. Rav likes to think about it this way “what’s the QBR doing internally?”. If the QBR is about “we had these many QBRs, these many EBRs,” is that good? He doesn’t know.

Back in the day, Rav recalls a meeting in which he needed to present some stats. The person that presented before him said “we did 65 executive reviews, 120 QBRs” and then Rav went up to present and said “I don’t have any of those this quarter but we did 90% logo retention and 100% net revenue this year and NPS is 8.5. And whatever we’re doing we seem to be going in the right direction.”

The person that presented before him had great activity, but he didn’t correlate those activities to the outcomes. And that’s the important thing that Rav wants CS leaders to do, start counting what you do in the terms of what’s important to the company. What’s the headline thing the company cares about at the stage it’s in? NPS if it’s early stage because you want to build awareness, at later-stage, it’s net revenue. So how can you draw a line between what you’re doing and how you’re presenting it so that’s meaningful?


  • We’re stuck in the old days––we’re not on the assembly line so let’s start breaking down the walls between teams

  • “Sales is about driving value, not revenue. Revenue is the outcome” (that applies to CS too)

  • Present your work to the company in a way that aligns with what the company cares about, not a running list of your activities

Shout outs

Thanks to Gain Grow Retain for hosting Rav on their podcast! You can go follow Gain Grow Retain on LinkedIn. And if you want to hear more from Rav, follow him on LinkedIn.


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