Scaling Customer Success and Revenue with Automation
CSMSecrets Podcast

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by Subha Shrinivasan

This episode has a Silicon valley entrepreneur as Guest, Dickey Singh!

Dickey comes from a strong technical background and is 100% a builder at heart.  The product portfolio includes software to measure customer satisfaction and feedback measurement systems, that enabled the Who is Who of the industry such as Apple, Google, Salesforce, Gartner improve CSAT by significant percentages. And this was acknowledged by none other than the LEGEND, Steve Jobs!

Subha: Hey Everyone!  Welcome to CSM secrets.

In this episode, we have Dickey Singh, CEO of, a serial Silicon Valley Entrepreneur, who is committed to helping apps go through automation and optimization in CS.

Let's hear from Dickey.

Hey Dickey, welcome to CSM Secrets. We are very proud and honored to have you as our guest today.

Dickey: First of all, thank you, Subha, for having me. You have had several influential Customer Success celebrities on your podcast before, and I am honored to be part of CSM Secrets.

But Really, The popularity of this show is totally attributed to people like you who, inspite of this being a new podcast, have graciously agreed to be part of this and shared so many insights that I have stopped buying books on amazon. I just use this podcast as a learning tool.

Once again, thank you much for spending your valuable time with us today.

Exactly, I was listening to some of your podcasts. A lot of friends there and valuable information.

Let's jump right in.

You are every bit an ideal Silicon Valley entrepreneur. Coming from a heavy technical background to having co-founded a few startups and now the CEO of Tell us about your journey and what landed you here in a product for Customer Success (how your previous experience in CustomerSat) is helping you in

Yes, I have been in Silicon Valley since the early 90s. I was in Virginia and Europe before that.

I am a builder at heart and love working at the intersection of product, engineering, and customers. I have built customer-facing products for customer satisfaction, feedback management, advocacy, behavioral analytics, and customer intelligence.

I have been part of products that have helped customers of all sizes, from fast-growing startups to enterprises including Apple, Google, Salesforce, SAP, eBay, Oracle, and Gartner, to name a select few.

At, we scale customer success and revenue growth using automation.

The premise is simple.

Eventually, several business functions become digitized over time.

For example, Customer service has chatbots. Product adoption has become digital. Prospect marketing went through the digitization phase. Customer Success and customer marketing are no different.

Your focus and rather area of expertise seems to be in automation & driving growth through the scale it brings. Tell us about your views and how fits in that thought process?

The need to scale is real for sustaining a SaaS business.

All because of increased competition, easier to use and deploy products, rising customer acquisition costs coupled with lower revenue per account, lower willingness to pay for features, and lower cost to switch to a competitor.

We spend a lot of time thinking about scaling beyond adding more CSMs or giving more accounts to CSMs or a pool or pod of CSMs.

We have a 1:many digital strategy, where we create podcasts, webinars, eBooks, infographics, and blogs for mass consumption.

We have many-to-many communities where many people help and learn from many others.

We scale by looking at patterns, documenting them, and creating playbooks. The CSMs can execute a playbook when they see a similar problem, increasing their productivity.

So where does fit in?

At, we provide 1:1 digital experiences using the power of automation and personalization at scale.

For us, the definition of scaling also includes making your product useful to all users and roles at every customer account — increasing stickiness and, therefore, retention.

Automation extends traditional scaling. For example, you can scale by automating playbooks where possible.

Scaling ensures the CSM is never the bottleneck between your customer success strategy and the customer.

How does work and who is the user persona it is designed for? What is the value add to the ecosystem it brings?

We know CSM-managed accounts are far more successful than unmanaged accounts.

By success, I mean better renewals, product usage and adoption, upsells and cross-sells, customer satisfaction, user advocacy, and more.

CSMs monitor the customer accounts they manage, create personalized content and presentations, and provide product and feature recommendations.

Cast automates several such aspects to drive product adoption and revenue growth.

First, generates relevant content, e.g., presentations complete with applicable recommendations for each user role at every customer account.

Second, a bot meticulously explains the presentations and recommendations. We call the bot a Virtual Customer Success Manager. The recommendations range from driving product adoption to renewals and revenue expansion, or what we vendors refer to as add-ons, upsells, and cross-sells.  

Third, any user's feedback or responses to product adoption or sales recommendations are recorded directly in your product for PLG products or your CRM for sales-led organizations.

The persona is attractive to is the CCO and the CS leadership responsible for GRR or NRR, renewals, account management, customer or retention marketing, and revenue expansion. Typically anyone managing scaled CS, a Customer Success program, and not just Customer Success Managers. provides value to both you and your customers.

Value for your customers includes improved customer health, product adoption, retention, advocacy, and impactful outcomes for each user at every account.

And YOU get the ROI of an automation tool! Seamless renewals, reduced churn, expansion revenue automation, improved Net Revenue Retention, advocacy, and ability to interact with users and non-users or the busy executives without requiring 1:1 face time.

Looking at 2022 and beyond, how should organizations look at and prioritizing automation in CS? What should be automated and what should not?

Automation is not for everyone.

But the ROI is impressive and gives you an edge over the competition.

With productivity tools, we talk about an ROI in percentages — 20%-40% improvement. With automation tools, we talk about a 8x-40x improvement.

So, how should organizations prioritize automation?

Start small. Start with just a couple of use cases and implement them. You'll get a rewarding ROI.

Our customers have several interactions with our business. Of course, all customer interactions must be positive, whether you're talking to a salesperson, the CSM, support person, or have office hours with an exec. Or even digitally on the website or in your product.

CSMs maintain these intimate relationships with customers when you have named CSMs and a small portfolio of customers. The problem is you cannot replicate white-glove experiences in environments when you have several customers, especially when you don't have that many CSMs for all those accounts.

So automating even the top positive interactions or what the industry calls Moments of Truth or emotional experiences can be very financially rewarding.

  • For instance, if you have playbooks that work for one-on-one named accounts, automate the top 5.
  • You could send a notification directly to the customer.
  • You could send a notification directly to the CSM.
  • You could send an explanation.
  • Ask the customer to fill out some forms.
  • Take the top few playbooks that work, and scale them.

I must add not every interaction can be or should be automated.

As of today there are about 300+ job openings just in the US for CS ops and relevant areas. Do you think this will go down with more automation and adoption of BOTS etc? Or it will only optimize the process?

I was not aware that there are so many CS Ops openings. I know there are several CSM openings. In tens of thousands.

We had a customer start a conversation with us because they had 18 CSM positions open and could not find the right people. I said to her just train our virtual CSM instead.

As I said earlier, Customer service, product adoption, prospect marketing became digital and automated in the last decade. Customer or retention marketing will follow the same.  

Several organizations resisted automating customer support. However, those who adopted early are leading.

I see similar things happening with CS and customer marketing.

Of course, I am biased.

What is your view about CCOs becoming CEOs lately? Do you see this as a good trend, would you encourage more of this? What skills should CCOs build?

You will see a lot more of CCOs becoming CEOs.

Let's look at why it happened.

It is easier to retain and upsell existing customers than acquire new ones. The cost of acquiring customers is 6.4 times the cost of retaining and upselling existing customers.

Of course, the product should work, and the customers need to be reminded continuously of the value and ROI they get from our products, so they keep renewing and buying more features, products, and services.

One, The cost of acquiring new customers has increased 60% in the last five years, while the willingness to pay for features has dropped by 30%.

Two, Because of the increased competition — and easier to onboard, use, and adopt products — the time, money, effort, and emotional cost associated with switching from one product to another continues to fall.

Three, Most SaaS businesses targeted an ARPA of hundreds of thousands of dollars. However, with PLG and self-service products, that's changing to serving more accounts at the ARPA of tens of thousands of dollars.

Now with lower switching costs, rising acquisition costs, lower ARPA, coupled with lower willingness to pay means as your CAC goes up, your profitability goes down. Therefore, you need to retain and make more money from existing customers to sustain as a SaaS business.

So, who is best suited to run a company where product adoption, retention, revenue expansion are vital to the growth? A CCO who understands customers well and can grow NRR.

You are off to the moon and likely never coming back and you are likely working from there. What are the 3 functions at work you would take along ( For example : CEO/Sales/HR/Analyst)?

  • I guess my CEO role,
  • A role that encompasses thought leadership around scaling CS using automation
  • The third is a role that lets me talk to CCOs and CS leaders to discuss problems that keep them awake.

Skills that you are looking for in aspiring CS candidates? Fresh grads coming into this function. What should they have a skill for?

Be customer- and data-savvy.

We will have more customers at lower price points. So data- and customer-savviness is vital.

One digital CSM can support an entire account base.

They can make he entire CS department look good.

If there is one favorite cartoon character that represents a good CSM, which one would you choose?

So which cartoon character is a problem solver? An advisor to his customers?

I can't of any. Maybe Remy from Ratatouille (ratatuie) is absolutely fearless when it comes to achieving his customer's goals.

You are most inspired by whom, why and what? Who or What drives you every day to work in CS?

It is hard not to pick Elon Musk.  

He is fun.

He works a lot.

He works on several hard-to-solve and high-impact problems.

What is the unique skill that you are bringing to the table that you think is impeccable for success in CS that others can learn from you?

I would say I bring a fresh perspective on scaling CS and revenue growth beyond the 1:many and many:many approaches.  

We can scale 1:1 customer success using the power of personalization and automation for every user at every account.

According to you, who is disrupting the CS space today? Who is helicopter landing and why?

So many:many communities with people learning from and helping each other are becoming mainstream.

Besides automation, Self-success powered by new self-success tools that minimize the CSM bottleneck will disrupt going forward in a big way.

How do you handle tough situations with customers? Your strategy in one sentence?

Apologize when you are wrong AND show you care by actions vs. lip-service.

What is the funniest moment you have had with a customer?

Moments. Hmm.

Several customer calls turned into investments for This happened not once but several times. The CEO of, the Senior Director at Product Board, the CCO of Securelink, an MD at Merrill, the CXO of all ended up investing.

What does Dickey the brand stand for in value? What should people say about you when you are not in the room, you aspire?

People should say the truth, regardless of whether I am in the room or not.  

I want to be known for being helpful.

People should add me on their speed dial. Second from top. Ha Ha. Seriously, I want everyone I work with to be a reference.

Finally a quote/thought/words that u want to be remembered by and any other self promotion.

I do not have any quotes, but let's talk about scaling customer success and revenue. Using automation.

Let's learn from each other.

Let's have a deeper discussion.

Go to to setup some time with me.

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