In this article, I’ll discuss my journey at Calendly, the initial challenges we faced when I joined tasked with building our customer success team from scratch, and the approach we took in aligning CS and PM to scale collaboration and ultimately, customer outcomes.

My name is Katie Christian, I am the Head of Customer Success at Calendly. My passions are hyper-growth companies all the way, people and culture are at the core of everything that I do, and last but certainly not least, is data. It's been a big driver for me, and it's a big passion.

My experience has ranged from customer experience all the way to the go-to-market side. Ultimately, specifically customer success, team support, onboarding, sales development, and dabbling a little bit on the sales side.

My tech career started at Sales Loft, I was the seventh employee way back in the day. We launched over five years two products, bringing them to market, growing from roughly 200k to 36 million, and creating the sales engagement space as it is today. A very exciting journey there.

Since I've landed here at Calendly, a phenomenal company growing so quickly and helping connect millions around the globe, scheduling faster, day by day.


I'm going to talk about my journey at Calendly. I've been at the company for a little over a year and a half. I was brought on board to build our customer success team from scratch so I'm going to talk about the initial challenges we had and the approach that we took.

Really, it bucketed down into three specific areas; alignment, experience, and partnership. I'll go over the amazing results we've had.

Calendly in February 2020

We had a customer success team of three, primarily handling more of a white-glove support approach, reactive versus proactive. In that, there were initial challenges in connecting with our product team.

Initial challenges

CSMs logged product feedback differently

First and foremost, the three CSMs that were on board all logged product feedback differently, which was a challenge.

Feedback lacked key requirements for product managers

In addition to that, the feedback actually lacked key requirements that resonated with our product team at scale.

Information mostly siloed, typically shared 1:1 with PMs

The information was mostly siloed so the CSMs would put it into a Word Doc of some kind and they typically go and share that one to one with a direct PM versus the entire product team or company.

No way to report on it at scale

When I arrived, there was no way to report on any of this at scale, I had to look into all of those individual Google Docs. I'm a lover of Google Docs, but not specifically for this use case.

Wasn’t making it onto our roadmap

Lastly, the most important thing was none of this was making it onto our roadmap, and eventually not making it to our customers. A lot of key initial challenges.

Initial challenges

I'm sure a lot of you are in similar places, or have been there and done that.

The approach

Now I’ll talk about what we specifically did to address these challenges, ultimately looking to create a scalable feedback process.


Ensure PM value

The first thing we did here, was I connected with the PMs. I said, "Hey, what do you need within the feedback that we're going to capture for it to resonate and be a value for you?"

They came up with very practical suggestions that were fairly reasonable.

Product areas

The first thing they asked for was product areas, "When you make these submissions, can they be specific to core areas of our product?"

Not a problem at all, simply asked them to help us create that list, gained alignment from both sides, and we implemented that into the feedback process, which I'll show you shortly.

User stories

They also asked us to write user stories, and help them identify the specific pains of the customer to the core areas of our product. So as a user, I would like X so that I can do Y. We just taught the CSMs how to create these user stories and boil down the value.

Once we implemented it, we found the PMs really did a great job of actioning that a lot faster because it was in their language, if you will.

Easily accessible

The last thing the PMs wanted was for it to be easily accessible. They all didn't have access to our Salesforce environment. They didn't want to look in Word docs, which is totally understandable.

Alignment: create a scalable feedback process

Increase visibility

Scalable reporting

What we did was ensure we had scalable reporting from the very start, which was a huge benefit and an increased lift from a timing perspective.

Real-time feedback

We made sure the feedback was submitted in real time to our product team and to the company if they wanted to review that.

Monthly updates

The last thing we did here in this particular area was monthly updates. Creating a detailed summary of all of the different things that were happening, the different bits of feedback, and showcasing some trends across the customer base.

The process today

From there, this is what the process actually looks like today:

Alignment: create a scalable feedback process

Align CSM process

You can see here in the middle I've got this surrounded by a little golden frame, but this is what the form looks like. The CSMs will put in the account, the contact specifically, a detailed description of what the customer was looking for, the feature request had a status aligned to it, and you can see the pairing just to the far right-hand side of what this looks like.

A high-level topic that was one of our PM requirements and so you can see we've got the example of admin controls on the right-hand side. And product feedback, was this a request, was it a nice to have? We've identified three different types there.

The urgency, and then the user story. The CSMs would have a simple button inside of our customer success platform where they click 'log product feedback', this form comes up on the left-hand side, and they simply pop it into the right-hand side.

Alignment: create a scalable feedback process

Increase visibility

As soon as that gets submitted, of course, we bring that to Slack for the rest of the company.

On the right-hand side, this is just an image of a Slack example, you can see our Salesforce feedback channel, we've got a bulk of product managers in here, different folks from around the company who are just interested in listening and in hearing about our customers.

This is what it looks like, I've certainly removed some of our customers’ more sensitive data from this but what it ultimately did was give instant access.

So a lot of times what you'll see is cross-functional collaboration between the core PMs on a particular squad, engaging with the CSM and saying, "Hey, this is really great. This is what we have on our roadmap, I'd love to have a 15 or 20-minute call with them to go deeper on this subject".

By actioning these things in real-time, PMs would be on the lookout and it just created more meaningful relationships last year as we scaled, of course, through the pandemic as well.

It really brought everyone together. Everyone was truly focused on our customer base, which was amazing. By logging this inside the CRM, we had scalable reporting, we then implemented it straight into Slack, which gave everyone instant access.

Then, of course, we do those monthly summaries, providing a higher level of detail, overall trends, and things of that nature.

175 submissions in Q2

This has been in place for a little over a year now and just in the past quarter, we've had 175 submissions from our customer success team. The revenue there from our current customer base is roughly 2.5 million.

We're really able to speak both from a quantitative side, but also a qualitative side. I think that gives us the ability to flex within the business for some of the more data-oriented folks, but also those who really want that voice of customer detail.

How do we create a phenomenal experience at scale?

Now we have this alignment between our customer success team and our product team, how do we create a phenomenal experience at scale?

What we didn't want was poor handoffs and things of that nature. We didn't want our customers to have that white-glove approach with the customer success team, and then feel a different experience with our product team.

That was one of the top areas of focus for us in this next chapter.


Customer engagement guide

We implemented a customer engagement guide. A lot of times people will say 'rules of engagement', I think even sometimes the phrasing of the program is really important.

Because no one owns the customer, the customer success team doesn't, the product team doesn't, we all have to be aligned to serve the customer. This engagement plan, or guide as we called it, ultimately had three key areas.

Golden rules

The first was if it truly was a customer success manage account, anybody engaging would just simply copy the CSM on the email so they had the insight.

To protect the customer experience, we also put a golden rule in place that if the customer had X number of touches over a 60 day period or a 30 day period, the PM had to pump the brakes and connect with the CSM to make sure it wasn't going to be an overwhelming experience of any kind.

We have some customers who love to have calls with our product team and would have as many as they could. We also have others where their time is pretty sensitive and we want to be mindful of that. Those were the two golden rules.

Prioritize by revenue and segment

We did prioritize overall engagement by revenue and the company segment. We created initially two categories.

  1. The first one required the PM and the CSM to have alignment prior to engaging on any type. These things were our highest priority customers, customers who were at risk, or customers who already had key projects in motion.
  2. The second category here allowed for more autonomy for the product managers. It only asked for alignment prior to engaging if the customer was in poor health.

In the process, we gave the PMs a really clear way to identify the health of the customer. Again, if everything was green, positive, and healthy, they could move forward, the only thing they'd be required to do would be to copy the CSM on those emails.

The PMs loved this type of approach because more often than not, they could run forward in that category too. But also the CSMs loved it because if it was a higher priority account, they knew they would have that alignment upfront to ensure the experience stayed on point.

Equipped PMs with resources

The final thing we did to ensure that experience was crisp across the entire customer journey was we equipped PMs with resources, and they were so thankful.

Quick customer lookups

We gave them quick customer lookups. In addition to the Slack prompts, we gave them a way to look into Slack and look up a customer detail view.

Email templates, pre and post calls

We also give them email templates so if you're a PM, you're probably not thinking about the best way to engage with the customer as to where the CSMs are highly focused on that.

So we gave them short and sweet templates to book calls but also post calls for follow-ups and recaps. They really appreciate it because it made their job that much easier in engaging with the customer and almost took off some of the pressure they had felt in crafting these emails.

Slide decks, with helpful templates

The last thing we did is while they were on calls, a lot of them wanted to showcase slides and research and things of that nature. Sometimes the slides weren't so beautiful.

So we created a specific slide deck for them and once we understood their flow, we created just a few templates within that slide deck that catered more towards their natural approach and allowed them to shine flawlessly with our customers on the call.

Experience: implement customer engagement guide

Streamline product manager workflow

Let's talk about how we gave them some lookups and some visibility into data, which we gave in two ways.

Slackbot lookup

The first is if they wanted to do a deep dive, you've got that here on the left side, we gave them the ability to have a Slackbot lookup. Because they didn't have access to our customer success platform or CRM, they could go into Slack do front slash org, put in their org ID, and in this they would get a return, think of 360 view of the customer where we would give:

  • High-level details about their use case,
  • The overall account,
  • Who key POCs are,
  • Health,
  • Trends - a little visual of a trend, and
  • Any real time updates of the most recent note or engagement with the customer.

The PMs really enjoyed that because they felt like they could go into the call knowing a bit more and not having to do as much discovery upfront.

It also made for a really positive customer experience because the customer didn't have to repeat themselves on a call something they've said to us probably a few times.

Export lookup

We also gave them the ability to export data at scale. Not every PM wants to look at each customer one by one, sometimes they have a very specific focus and they want the ability to say, "I want to know specifically all customers who are interested in group scheduling".

They would be able to pull a report from all of the customers who have submitted product feedback in that specific category. What we would do is generate a list for them showing the overall health, revenue, latest communication on that account, and export that in detail.

From there, they had a bulk list that was targeted specifically to what they needed, which was really fantastic.

Experience: implement customer engagement guide

How do we partner on customer outcomes?

Now the CSMs and the product managers were partnering seamlessly across the business, and our customers were having a really great experience as well, we said how do we partner together on outcomes internally, inside the business?

Now that we have the full circle, we have the customer success manager, the product manager, and the customer all aligned, and we're capturing these really brilliant insights.


The two things here we did to take it to the next level were collaboration and communication.


Embedded CX Liaisons in each product squad

Around the collaboration side, we actually embedded, we call them CX liaisons at Calendly, members of our CX team in each of our product squads.

That way, as they were working on their roadmaps, and things of that nature, we could be giving feedback along the way. These today are bi-weekly syncs and they're roughly half an hour to an hour, depending upon the topic of discussion.

Invited PMs to present in quarterly fireside chats

The other thing we did is invited product managers to present quarterly in a fireside chat setting. They would bring their specific core area of our product with maybe five to 10 slides of where they're going, what they're doing, thinking, or working on.

Then we just have a fireside chat, once they're done presenting and it really allowed

  1. An increase in relationship trust and just overall communication, and
  2. It led to some really brilliant ideas across the organization.

PMs did some really brilliant things that I'll share with you in just a moment.


Implemented monthly and quarterly summaries

We started to implement both monthly summaries right upfront and then we started to turn that to quarterly to showcase larger themes across the business.

Created a format for escalating product risk

In that, we also created a format on the customer success side to escalate product risk.

We were doing those one-off submissions and things of that nature but we started to see risk across the customer base and created a really great format that was simple for everyone from a frontline rep to our executive team to consume.

That was really key initially and early on.

Partnership: drive customer outcomes together

Let's talk results, my favorite part.

The results

Increased roadmap alignment

Through this collaboration, through the increased product feedback process, the communication that followed on a variety of different cadences, which really had roadmap alignment.

Increased release frequency & customer satisfaction

What this did was increase our release frequency, and ultimately improved customer satisfaction.

360 view: the approach, the outcomes and the overall result

The outcomes

Capitalized on in-the-moment customer feedback

Literally, as CSMs were getting off calls, they would log the product feedback. PMs would write back within five minutes and say, "Let's jump on a call with this customer and learn more about it".

Customers truly felt heard, which was amazing.

Close feedback loops faster both internally and externally

We knew what was being prioritized on the roadmap and what wasn't. The PMs and CSMs were communicating at a higher level than ever before in the business and everyone really felt aligned.

PMs provided ‘quick wins’ on UI and features improvements

The PMs with that information also provided some amazing quick wins. So as a CSM would post a simple change, or what appeared to be simple in the UI or to a specific feature, sometimes PMs would turn that around in a couple of days, a week, or two weeks unexpectedly based on the feedback they had submitted.

It showcased to CSMs, the more we log this product feedback, the more our PMs are listening, actively innovating around it, and creating wins for our customers. We had a ton of amazing energy around this.

CSMs shared customer emails of thanks and excitement

Then what we did is once we had those quick wins released, I always said to the customer success team, make sure we go back and we share this with product.

We give them kudos internally through a channel that we have, we share these wins and emails in Slack of a customer's just truly rejoicing from all areas of the globe, about these wins and these updates inside of our product and just thanking us so much for listening to them.

It just brought everyone together, through the last year of the pandemic, ultimately focused on our customers and driving key outcomes for them.

Overall result

The overall result here ultimately led to yes, an increase in roadmap alignment but increased release frequencies, and overall increased customer satisfaction.

Where we had risk, we no longer have risk. We have so much innovation in our roadmap.

Where customers are excited about Calendly, asking about multi-year subscriptions and locking us in for the long term and things of that nature. Truly music to our ears in customer success.

But without that product partnership, it simply wouldn't be possible. That's the journey we've been on for the past year. It's been really fun. It's been full of learning, challenges, and opportunities.

I hope this was helpful and gave you insight into what we've been up to around building a strong partnership between product and customer success at Calendly.

Thank you.