Human-assisted Conversions in a Self-Service SaaS — Calendly’s Journey

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Again in 2015, Joel York mapped out the three SaaS enterprise fashions you could possibly undertake, relying on the pricing and complexity of your product.

Reduce to at the moment, self-service companies are dominating the market. That is evident from nearly all of the latest SaaS IPOs — Slack, Fiverr, Zoom, DocuSign, Dropbox, Eventbrite, SurveyMonkey… It’s a protracted record, however you get the drift. 

During the last couple of years, companies who had been rooted within the promise of self-service and product-led development, have been capable of increase their income with human-assisted gross sales fashions, as they uncover newer buyer segments. These inside-sales groups are required to facilitate higher expansions.

Corporations can all the time be utterly product-led. And even having a gross sales workforce doesn’t imply you’re not product-led. It simply relies on the way you’re utilizing your gross sales workforce.

Wes Bush

But, sure questions stay.

Do self-service SaaS firms want a gross sales workforce? When ought to self-service companies think about introducing a gross sales component? What’s the influence on the product, buyer acquisition, and pricing with the addition of a brand new gross sales mannequin?

What actually is an effective monetization technique for product-led SaaS? 

In case you are a enterprise that’s largely self-service or has a hybrid mannequin, we’re fairly positive related questions plague your online business. 

We spoke to Calendly, a scheduling software program, an OpenView portfolio firm, and a Chargebee buyer, on what it takes to crack product-led development. For Calendly, virality is vital. From product-led to sales-assisted virality, they’ve managed to onboard tens of millions of customers with this trick.

We go deeper into how Calendly went about:

  1. How Calendly overcame the battle between balancing income technology and buyer development when it got here to monetizing their 100% free product
  2. How they went on to bake in human-assistance that transitioned from reactive to proactive, regardless of the product being primarily self-serve
  3. How they integrated adjustments in buyer acquisition and gross sales processes, and inside processes as they launched “sales-assisted virality” into the product
  4. Why product-led companies ought to intention at being 100% self-serve as they begin out
  5. How investing in help has had a dramatic influence on activations and conversions

Right here goes… 

Having a largely self-service enterprise mannequin that began off with a totally free product, when and the way did you resolve to monetize Calendly?

Tope: Calendly began as a 100% self-service, free product in 2013. By the point we reached 10000 customers, we needed to monetize the product and there have been two main issues we would have liked to determine for that: 

  1. The packaging — which options to truly cost for and the place to attract the road between what’s free and what’s paid 
  2. The pricing — as soon as we felt assured about what needs to be free and paid, we needed to decide what to cost for it and what the perfect value vary needs to be 

These considerations got here from a really sensible place — we didn’t need to elevate extra money, proper? And if we did elevate extra money, we needed to do it from a spot through which we might have a whole lot of leverage. 

(For the primary query) we had been getting a whole lot of characteristic requests, like eradicating branding and easing utilization of Calendly in multi-user state of affairs. They’d say, “I’m an administrator from my firm and I deploy Calendly to 10-20 folks in my firm. How do you make that simple for me?” 

We might push these requests as a characteristic flag and allow them to know what it might price. Whereas some individuals who made the request weren’t keen to pay for it, we discovered higher proportion of them had been really keen to pay for it. 

So we examined the packaging and we ended up promoting the preliminary paid bundle the place you could possibly take away branding. We additionally restricted the options within the free bundle. So, it wasn’t a query of introducing new options, we had been additionally taking options that had been as soon as free and moved them right into a paid plan. 

And that half was tough as a result of the expansion of our enterprise is generated by the virality of our product, since day one. And due to the free nature of Calendly, we diminished the obstacles to entry and made the product higher. 

So once we needed to cost for the product, we had been conflicted with balancing income technology with development. As a result of, for those who begin charging and put up a paywall, you could possibly probably see folks depart the app, which might harm us in the long term, it’d decelerate our development.

Now for us, as a result of now we have a big pattern dimension from being a free product, we might see utilization patterns and the way folks would use the product. And so it got here down to 2 usage-based fashions — (i) charging the folks based mostly on the variety of conferences scheduled in a sure interval? Say, free customers, get 20 conferences every month? (ii) Or get customers just one availability sort or occasion sort. 

The primary method felt punitive and the consumer expertise wouldn’t have been nice. We thought that’d be a nasty expertise for a Calendly consumer and a horrible expertise for the individual you shared your hyperlink with. And we simply thought it was unhealthy for everybody throughout. Positive, we might convert some folks, however we thought that, extra importantly, that’d be a unfavourable expertise for the product and model and it might in the end push folks away. And it wasn’t predictable. 

We settled on the Occasion Sort-based plan for all these different causes. It was predictable. You possibly can opt-in to get into the paid plan. At that time, you resolve that you just need to begin off with a distinct availability rule set, then you definately would improve. So we felt that that’d put you in cost, put you in management. And in addition, we had been assured from the utilization patterns that we noticed with folks, that by the point they determined that they needed to make use of a second occasion sort, they had been dedicated to the product. 

So for probably the most half, we had been monetizing the individuals who had been captive. They weren’t going anyplace at that time. They used the product for a while. They felt comfy. They’ve seen outcomes with it. And in pricing 101, you need to value probably the most captive folks that you’ve got. We felt like that gave us a very nice steadiness. And that’s the place we began. 

And so, we did a whole lot of the testing manually. As soon as we found out the best packaging, we noticed that individuals had been changing at a reasonably good price. And that the value was not a difficulty for individuals who examined throughout totally different value factors. I believe the bottom we examined was $5/consumer and we examined all the way in which until $10/consumer. So, the conversion charges actually didn’t change throughout totally different value factors. 

As soon as we figured that out… So we used a guide course of to determine what the best packaging and the best pricing is, then we rolled that into the product and made it 100% self-serve. As soon as we found out the profitable bundle and pricing, we simply automated all that. 

You had talked about about monitoring the utilization patterns to grasp what options clients are keen to pay for. The time period for this that’s selecting up — fairly just a few companies name it product certified leads — contact factors within the product that pushes a consumer from sign-up to activation to get them to maneuver to a paid plan. Proper. How does Calendly do this?

I’ll provide the abstract of it… The necessary issues that we cost for are our integrations, workflows, workforce administration capabilities, and the variety of occasion sorts that you’ve got; availability guidelines in different phrases. These are the 4 massive levers that we, that now we have from a pricing standpoint. They usually are also tied very carefully with the most important retention hooks-me-up inside our product. 

Q: Catering to the B2B section means your product is rarely actually 100% self-serve, proper? And Calendly additionally has a gross sales workforce that actively reaches out to prospects. What prompted the necessity for a sales-driven method together with the self-serve mannequin? 

Over time, as we started to monetize it, we really started to check out a hybrid method. 

The following factor we kinda seen was that despite the truth that we knew the profitable system and folks might do it on their very own, we began noticing a development through which folks would come to us and say, “Properly, now we have 2 customers. We’re pleased with it. We’re serious about increasing to 12 customers. We need to discuss to any individual.” Proper?

And initially, we would offer them with assist paperwork and extra content material on our web site hoping extra of them might self-serve. And that helped in some circumstances. However folks nonetheless saved coming again to us. 

So I acquired on calls with them. That they had questions on easy methods to use the product, that they had questions on issues that they’d prefer to see within the roadmap, to provide them confidence that they had been betting on the product and firm. As soon as all these issues had been addressed, they felt just like the product path was the identical path they needed the product to be headed in, after which upgraded. Just a few months after that, by me helping them, they went up from a 2-user account to a 12-users account… By 6-Eight months from then, they moved from 12 customers to 100 customers on their very own. 

The identical factor occurred with just a few different accounts.

So we noticed in a short time that, at any time when folks needed to roll one thing out to a bigger group, sometimes, they really feel extra assured once they can discuss to a human being about doing that. Loads of occasions, the questions I answered for them had been questions that had been current on our web site or our docs. However they needed to speak to a human being.

We noticed that by serving to them, we had been capable of assist them convert and along with that, a whole lot of these firms went on to develop so much on their very own. So, that is the place we started to debate if this works, why not add extra people for it. That was the evolution of our 100% self-serve again to a hybrid method.

Initially, it began reactively however over time it turned proactive. To the extent that now we all know these use circumstances that develop very properly. So, at any time when we see these use circumstances, we’re proactive in providing help, to get on the telephone with folks. As a result of we all know that if we will get the preliminary conversion with them, these preliminary 10-12 customers, they’ll go on to develop to 50, 100, 200, 300 customers at a time. So it began as a reactive factor and over time it moved to a proactive method. 

However even then we don’t do all of our use circumstances. There are some use circumstances that we all know that the enlargement alternative isn’t definitely worth the economics and we don’t actually put a gross sales workforce to these. We simply allow them to self-serve. However the ones that we all know will develop to a couple 100 customers, we proactively attain out to them and use that hybrid method. 

And over time we are actually in a section the place we’re pushing the envelope even additional and proactively reaching out to these folks to find out what are their enlargement alternatives inside the firm. 

So 100% self-serve. It could grow to be 90-10 with 90% self-serve. And I believe the path we’re shifting to now, over time it’ll most likely be like 80-20 and 75-25. Nonetheless closely skewed in direction of self-serve. However as we search for enlargement alternatives within the enterprise and the mid-market, we now understand that it’s very tough to try this by means of 100% self-serve. 

Our first roughly $4m or so in income was self-serve. After which we had gone from $4M to multiples of that now, and the sales-assisted concepts have performed an enormous half. 

If you speak about a gross sales workforce that’s proactively expansions, other than the variety of customers, what else do you search for by way of enlargement? What different metrics/worth characteristic do you pitch to your enterprise buyer that makes them say, “Sure! We’d like that”? 

Many firms have taken many various approaches. For us, the way in which we develop inside an organization is primarily by the road of enterprise. To get an organization like Lucidchart for instance, and even Dropbox, it’s a necessity that everybody has throughout the corporate. Loads of these firms, once they go to Enterprise, they undergo IT and make a case to IT that you’ve got all these siloed deployments of merchandise. If we might convey all of it beneath one home that’s managed by you, we may give you management of your organization’s scheduling, with the best safety controls. 

So we communicate extra to the advantages for that exact perform. And we don’t have a place on whether or not you might have 10 totally different Calendly accounts inside your org or whether or not you might have one account for 10 customers — we’re detached about that. We simply need you to know the methods through which… The advantages you stand to achieve by rolling it out to your complete division, your complete perform. That’s the method that we take. 

The reason being… What sometimes occurs is that you just get a person consumer who begins utilizing Calendly. However they don’t have the permission or the authority to combine Calendly with Salesforce. And in that firm, they aren’t getting the complete good thing about Calendly, due to the person consumer who doesn’t have the authority to implement that extra use case. What we’ll do is we go to that particular person consumer. 

We assist them perceive a few of the different methods through which firms like them are utilizing it and we ask for an introduction to the division head or the individual they suppose we needs to be having this dialog with. Clearly, we educate them on the advantages and worth proposition after which as soon as we get that introduction, we make the pitch to that individual and that’s sometimes how we transfer from having one or two customers in Calendly to 1500 customers. That’s been the simplest method that we’ve discovered. 

Q: So, it’s virality inside the workforce. Or inside the group. Or in higher phrases, sales-assisted virality.

Precisely! After which the online that we try to crack in a repeatable manner is — “okay, you’re utilizing it in gross sales, however we’re additionally used properly in recruiting, and your recruiting workforce can profit from this — are you able to get me an intro to any individual in your recruiting workforce?” 

That play is a little bit bit harder however explaining inside the similar perform is fairly good. We figured that out, we try to scale it, however that basically works for us.


For many companies, normally, the primary million is the toughest million once you’re making an attempt to get to the primary million. Then 5 million is the toughest… So at every of those levels of your development, might you discuss in regards to the greatest adjustments with respect to your gross sales course of, by way of the way you purchase clients in addition to your inside processes?

I believe the most important factor that we’ve executed, so we sort of knew the place we gained earlier than, proper? However actually within the final 12 months is once we’ve executed this. We checked out our knowledge — of all our gross sales assisted offers, what proportion of them are coming from inside gross sales or buyer success? What’s our win price for gross sales to totally different audiences? We seize our win price by what we do, once we’re closing a sales-assisted deal, the use case, the vertical. After which we sit down and examine the win charges throughout all of the totally different buyer segments.

After which we in contrast the LTV throughout all of the totally different buyer segments. And it turned very clear to us that there are about six or so use circumstances that now we have within the enterprise section. The highest use case is head and shoulders rather more profitable for us than the others. Earlier, we had been reluctant to prioritize in a one use case over the opposite. 

However once you have a look at these numbers, it turned very simple… Even in a small firm like ours, it takes so much to vary that mindset the place we’re going in any case offers to principally going after these two or three offers. So we needed to convey this modification all throughout the corporate. All the pieces else is self-serve, proper? 

We’ve made that line extra intimate, from the way in which we compensate the reps within the quotas to our gross sales ops groups and the way they prioritize which alternatives to behave on as we undergo these offers the place we get safety questionnaires and need to undergo their authorized course of. Everybody from buyer help and success has a really clear understanding. We love all our clients, however with regards to very particular use circumstances, we put a salesman on. 

So aligning that throughout the corporate has been as one thing that we introduced on up to now 12 months. And it’s the identical factor for us with regards to prioritization of characteristic requests. We, by and huge, need to construct options which are higher, that shall be adopted by 80% of our consumer base. 

The one exception to that’s with regards to these strategic consumer segments that we’re going after. For example, with regards to integrations, we prioritize a really strategic customers section. However even inside that group, they’re not all homogenous. All of them have totally different wants. They’ve various things that we’re optimizing for. And even inside that group, we construct for 80% of them. 

We make sense of all of the characteristic requests and we are saying which consumer group that is utilized to. And if it doesn’t apply to 80% of both, you already know, the strategic segments or 80% of the consumer base. It’s not one thing we needs to be constructing.

So for those who undergo our integrations, you’ll see that we’ve emphasised a lot of our integrations with CRMs, applicant monitoring programs, advertising and marketing automation platforms — we’re actually targeted on the customer-facing capabilities inside an organization.

In your discuss in SaaStock’17, you spoke about automating elements of the product and lowering friction for conversion. As you scaled, how did you optimize for conversions inside the product?

It’s fascinating. I’m a buyer of many SaaS merchandise myself. However there are firms a lot larger than us, which have mature merchandise, which were round for a very long time and so they’re not doing half the issues to handle my billing inside these merchandise. They usually can do this with Calendly. 

So, we use Chargebee and Stripe. And each platforms enable these capabilities. We automated a lot of the billing use circumstances on day one, however there are nonetheless just a few outliers that we simply needed to do manually and over time we’re chipping away at these.

And that’s okay. It’s okay for those who can’t absolutely automate on day one. Proper? 

Let’s say, for instance, I’m in the midst of an annual plan and I need to cancel two months into plan. So I ought to have the credit score for 10 months. These sorts of conditions, we aren’t absolutely automated to the consumer at the moment inside Calendly, like a human being requested to go and calculate how a lot time you might have left, is a credit score due, and do all these various things I don’t suppose that it’s necessary to automate these edge use circumstances on day one, however you’re going to succeed in a scale the place it’s going to be very tough to handle all these folks if you need to do a whole lot of issues manually. Proper? You are able to do it manually within the early days however you’ll want to start automating it over time. 

The way in which I’d prioritize automation is, I’d prioritize all of the issues that enable a consumer to create a brand new subscription, and add extra customers to that subscription. I believe folks usually could be rather more affected person about getting refunds, proper? They are often affected person about switching from bank card to buy order. I believe that most individuals perceive and settle for the truth that they’ll’t do some issues mechanically…

However my very first gross sales supervisor’s recommendation was that at any time when somebody is able to offer you cash, you shut up and take their bank card. 

So something that permits any individual to start out paying, I’d automate that on day one. So if I’m able to create a subscription, you shouldn’t give me any room to vary my thoughts.

Make it simple for me to enter my bank card and begin that subscription. If I’m serious about including 10 extra customers, it’s best to make it simple. I shouldn’t have to attend. The second that I’ve that thought I ought to be capable to like go into your product and add these 10 customers with out asking anybody.

That is true for enlargement as properly. So I’d automate all these issues on day one.

What can be your recommendation to companies which have constructed a product for self-serve? Would you need them to know that that could be an opportunity sooner or later the place they could have to take a look at a gross sales method and the way ought to they be going about it?

Right here’s what I believe — it’s very simple so as to add gross sales help or human help in a while. I believe it’s a lot more durable to start out as a sales-assisted firm or human-assisted firm after which attempt to do self-serve. That’s my expertise. 

And I’ll inform you why. As a result of even inside self serve, you might have a whole lot of instruments, proper? So you might have a ticketing system, you might have a data base, you might have product analytics, you might have a middleware-like section that connects your, your knowledge to all these totally different apps and platforms that you just’re utilizing to offering nice buyer expertise.

You’ll be able to all the time intervene. A human being can all the time intervene at any level. So you might have signed up, you could be utilizing the merchandise, however once you join, now we have your electronic mail, proper? So our advertising and marketing automation can attain out on to you. Even when it’s 100% self serve, you may all the time lay on human help when you’ll want to. 

So, if I had any recommendation for anyone, I’d say deal with 100% self serve after which start to determine the place you may go deeper or the place there’s extra worth to extract out your clients and attain out to these and do this with a human being. And if it begins to work, discover a manner in which you’ll scale it up, whether or not it’s by means of the product or by means of people. That might be my advice.

What’s the one factor that product-led companies should completely put money into proper from the early levels of development?

I believe for self-serve companies, help is a vital pillar. On our buyer help facet, we publish the said SLAs that now we have on our web site. And we attempt to beat that by multiples. And we discovered that by, by doing so it’s had a dramatic impact on activation and conversion. 

So I suppose there’s nonetheless the self-serve component, proper? However when folks do have points, how do you give them a solution straight away and what impact does which have on activation and conversion? That’s one of many issues that I needed we might have paid extra consideration to… We’ve all the time had good customer support, however we’ve simply been a dramatic distinction within the activation and conversion by, by persevering with to shrink that SLA down. So, that’s one other lever that a whole lot of self-serve firms have, that perhaps they aren’t serious about.

And it’s additionally about content material creation and optimizing along with your data base. We need to reduce down as many tickets as doable so that individuals can self-serve. But when folks need human help, the help response must also be lightning quick.

Divya Ganesan


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