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Podcast Recap: The Evolution of Customer Success at a Growing Startup

Updated: Jan 31

Startups are booming! 

It feels like every time we blink, there’s a new company out there. In 2016 alone, 69% of U.S. entrepreneurs started their business at home. And in 2018 there were 145 “active unicorns” in the U.S. collectively worth $555.9 billion.*

Getting Customer Success right from the very beginning is a must. Allison Pickens, the former Chief Operating Officer at Gainsight, knows exactly what this journey is like. She’s helped Gainsight grow from it’s early days to what it is now. 

This post highlights the journey of a startup, the strategic planning needed for your Customer Success team, and the importance of having a strong relationship between Product Managers and Customer Success.

The details

In this post, we are recapping the episode “Why Customer Success and Product Management Are The New Sales and Marketing, How To Approach Building and Scaling “Services” As A Revenue Line & How To Build A CS Team On A Tight Budget” by the SaaStr podcast. 

Allison is a leading expert on how to grow recurring revenue and basically helped create the Customer Success software space through Gainsight. She advised thousands of startup founders and fortune 500 CEOs. These days, she’s an investor, sits on advisory boards, and has authored a book. 

The SaaStr podcast interviews the most prominent operators and investors to discover their tips, tactics, and strategies to attain success in the fiercely competitive world of SaaS. 

Here are the 3 takeaways from this episode

  1. The impact of Customer Success throughout a startup’s growth  

  2. Strategic planning from day 1  

  3. Product Management & Customer Success is the new Marketing & Sales 

The impact of Customer Success throughout a startup’s growth

To understand what’s needed from Customer Success, we first need to know the stage of the startup. 

For this, Allison likes to use David Skok’s definition of the 3 phases of a startup’s lifecycle:


  1. Stage 1: you’re figuring out Product/Market fit

  2. Stage 2: you’re figuring out Go-To-Market fit

  3. Stage 3: You scale your Go-To-Market strategy 

How does this look in Customer Success? 

During the first stage, Success is important for building empathy. This team can help you uncover the pain points customers are having and how the product can evolve over time to help address them. Often founders are building products to solve for their own needs but as they build a client base, it’s not enough to build for themselves and Customer Success is critical in ensuring this doesn’t happen. 

In stage 2, the Success team takes the form of thoughtful problem solvers. They have to figure out how to automate workflows and build a Customer Success playbook that will scale in stage 3 in a repeatable way.

Lastly, in stage 3 we see specialization like Support, Customer Success Operations, and sometimes Account management and Services become important. We may also start seeing the selling of services to offset the cost of investment in clients and further automation through the product and in-app walkthroughs.  

Strategic Planning from day 1 

One thing that’s prevalent through all stages is setting Key Performance Indicators or KPIs. 

Strategic planning is relevant to Customer Success. During this process, a company aligns all functions around the most important priority at the organization. In order to deliver successfully on the needs of the client, you need everyone at the organization oriented around the customer. 


Allison encourages Customer Success leaders who don’t have a cross-functional strategic planning process that’s working for them, to start focusing on it! It’s the core thing they should implement. Strategic planning is about alignment around the essential unit of the OKR, Objective and, Key Result. A key result can be defined as a target/metric you want to achieve and objective is the spirit of the metric, it’s the way you’re going to tackle that metric. 

An example of an objective, Allison shared, would be to elevate the way we’re working with our client by selling to higher-level buyers as measured by a key result or KR which is the total bookings we have at our company. The key result should tie to your key metrics in your P/L, this might be a metric related to bookings, to your gross margin or operating margin. The objective you pursue should be tied to those metrics. Once you identify the most important priority for the company, you also have to ensure that the primary focus of team members is in line with those priorities. 

What does creating an OKR look like?

Like a lot of us can relate, Allison can’t say they’ve mastered creating OKRs at Gainsight. But they have a strategic planning process and this has been the first year where this has been a big focus on the granular level so they’ve learned a lot along the way. The biggest lesson around creating a strategic plan has been the importance of feedback.

You need that feedback from across the organization on what’s going well and what’s not. Allison has gathered this feedback through roundtables, offsites, surveys, etc., and has set up a forum where extended leadership teams can talk about what’s going on in the business. 

The second lesson has been the need to align with what’s going on with the finance objective. It’s very important that they’re tied together because if you plan for something out of budget, that’s a problem. 

Making sure OKRs don’t disincentive the team

There are some OKRs called “moonshots”, it’s a shot in the dark, and achieving it is unlikely. When you create a moonshot OKRS, it’s important to note that this goal is a moonshot, and leaders should figure out how to incentive their team based on some other number. For example, if they achieve objectives that are more within their control. There’s another goal called “roofshot”, the roof is within reach so it might be that compensation and other forms of performance management are tied to that roofshot OKR. 

Measuring OKRs

During the quarter when tracking progress on KR, if Allison and her team are forecasting below the target she wants to understand why they are targeting below and vice versa, she wants to know what’s contributing to that success. It’s important to learn along the way and make note of factors that are impacting the progress. 

Another thing when forecasting below the quarter is the need to creates a path degree, similar to a waterfall chart that shows what are the steps needed to take that would lead to meaningful improvements in that KR up until the target. Then at the end of the quarter, hold a retrospective. One thing they’ve done has been creating a doc that includes all of their learnings. She finds that it’s much harder to do this but a lot of actionable items come out of it.

Product Management & Customer Success is the new Marketing & Sales 

The relationship between Product Management and Customer Success has always been an essential collaboration. Yet, we’ve failed to draw the connection on how married these two functions need to be to drive the success of a company. 

In Customer Success, you see a very important pain point which is teams trying to figure out how to scale. The most valuable asset is the product itself so if we see that Customer Success is plugging gaps by creating workarounds, they have an opportunity to work closely to help the Product team fill those gaps. That way the Customer Success team can spend less time on technical troubleshooting/providing band-aid solutions and spend more time on renewals and driving expansion over time.

From the Product teams’ perspective, they need Customer Success to know whether they’re building the right thing and gaining greater confidence around their roadmap. 

Improving how Customer Success gives feedback to Product 

One thing Product has seen is that the Customer Success team is often not sharing feedback in a way that resonates with the Product team. Allison finds that Customer Success people are situational thinkers, they understand holistically what’s going on with the client. However, the Product team doesn’t tend to look at problems on an individual basis, they’re more systems thinkers looking across a client base and looking for trends. So Customer Success with its situational thinking can point to anecdotes and hunches the Product team can then explore and develop hypotheses for their trends. 

How Customer Success sometimes stunts scaling 

Here’s something crazy… 

Sometimes Customer Success Managers are too good.

When a Customer Success Manager takes so much ownership, they run the risk of solving problems that are not scalable. When this happens, what we need to do is redefine what a good CSM is. Maybe they don’t try to own the problem all on their own but serve as the person that bridges Customer + Product to try to solve that problem. This will also allow them to scale their job. 

Both of these functions really need each other. Putting processes in place to improve how they work together is key.

Measuring product adoption in Success + Product 

The first step is to identify the north star adoption metric that the organization is aiming for. That may be the number of times a customer is completing a certain high-value action in your product. 

In Customer Success, we’re often looking at problems and opportunities at a customer level. When looking at the total aggregate volume of a particular action in Customer Success, there’s a risk because that volume might be concentrated in only a couple of clients. If that’s the case, the data may not represent whether your client base is actually healthy. So what we need to do is create a health score that is based on that north star metric? Essentially, we’re trying to move as many clients as we can into the green level of that health score.

On the Product side, Product Managers tend to think about adoption metrics more on a feature level or module level. In the world of product, they might want to look at how we contribute to that north star metric through the appropriate adoption of that specific feature or module. 

So who’s accountable? 

Allison has seen companies that have joint accountability and while it’s great for collaboration, sometimes it creates a delusion of accountability. In that situation, it might be valuable to have 2 metrics contributing to that north star metric. For example, in Customer Success, the primary metric might be the average health score across the client base which could be driven by the north star metric. whereas in Product organization, the metric might be more oriented toward measuring ROI on a new feature release.


  1. The role of Customer Success is different throughout each phase of a startup

  2. Regardless of what phase of the startup lifecycle a company is at, strategic planning is prevalent

  3. Customer Success can stunt scaling at a company by being too good

Shout outs

Thanks to the SaaStr Podcast for hosting Alison on their podcast! You can go follow SaaStr on Twitter. And if you want to hear more from Allison, follow her on LinkedIn



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