Behind the Scenes of Calendly Sales Growth
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Rachel Williams is the Director of Sales and Partnerships at Calendly. Calendly is a simple, yet powerful online scheduling tool that eliminates the back and forth of scheduling, giving users valuable time to be more productive in their daily lives. Used by over 2 million people every month, the tool is experiencing sustained growth rate year-on-year.
Rachel has been managing sales at Calendly for 2 years now after transitioning from Marketo and is passionate about the women in tech community. We got to talk about her journey in sales at Calendly — about consistently hitting quota with a team of three, and her role as a mentor.
You run a tight team of three, including yourself, and cater to the needs of millions of users. How does a typical day at Calendly go?
Our days are different but with mostly the same elements and a combination of factors.
Usually, each Calendly sales rep has an average of three to five scheduled calls per day to accommodate the volume of leads that come in. And those can either be initial exploratory calls to demos to project follow up calls.
“For someone in sales, I would say that no two days are alike but we do a lot of similar activities every day.”
But the majority of our days are spent tending to scheduled calls and emails. Any time we have a call with a customer, we always send an email to recap the conversation and include any applicable deliverables or resources that would be helpful for that phase of the project.
The rest of my team’s time is spent with the other activities needed for their opportunities. They may have a few larger opportunities that require more strategizing or assistance from the product or security team. It really all depends on what is on their plate for that day.
What does Calendly sales cycle look like?
We run a full sales cycle with all the inbound requests that come in from our website and our support channel.
Our website has a dedicated page for teams which guides larger teams looking for a scheduling solution. So our team handles the requirements of those teams that have 10 or more people using Calendly on the same account.
The prospect fills out the form, and one of our reps reaches out to the customer — running a full sales cycle with discovery calls, demos, and any other steps that are needed to close the deal.
And how long does that usually take?
Since my team doesn’t interact with smaller teams or individual buyers, I can only comment for the larger teams.
But the sales cycle varies based on several factors like, at what point in the buying process are the leads coming in? Are they just exploring Calendly or have they used the tool in some capacity, or are they ready to get started immediately?
The size of the team makes a difference too, in the sense that larger projects can sometimes be more complex with more steps. Our sales cycle can be anywhere from about two to four weeks on average.
You lay the foundation for the sales quarterly goals and lead the way forward. How does a typical day look running the sales scene?
I have two main initiatives that I work on. First and foremost, my role is that of a mentor and coach on my team.
I try to sit in on several sales calls each day. Firstly, to coach and help my reps grow in their sales skills, and also to continue listening to what our customers are saying and the pushbacks we are getting. That way, I can figure out if it’s a product feature that we need to work on or a process that we need to enhance or whatever else that’s needed.
Secondly, I’m always looking at how can I provide my team with the resources they need to be more effective with their time. When they are selling all day, I want to remove as many roadblocks as possible.
“By getting the team the tools they need to be more efficient, they get to focus on selling instead of worrying about the administrative tasks.”
I also work with other departments here at Calendly to ensure smooth handoffs to our customer success team and create easier processes for my team. A lot goes into keeping this a well-oiled machine.
What are some of your favorite tools that you are using right now?
We use TextExpander, which is pretty awesome. It basically allows you to create templates for emails. Phrases that you can just shorthand type into emails. It’s a huge time saver. A lot of times, you wind up sending more or less the same phrases so it makes sense to have a tool that can help you type these commonly used phrases quickly.
Instead of sending a templated email, what I like to do is create a library of commonly used phrases. That way, I can quickly type out an email that’s a compilation of those phrases. An email that would normally take me 15 minutes to type out manually takes me barely 3 minutes with TextExpander.
I have to say, I love Calendly. I use it numerous times every day.
And Calendly is integrated with GoToMeeting. What used to take 3-5 minutes to create a meeting now is all completely automated on my behalf. I just send out a link to my customer and it’s all taken care of from there.
Let’s talk about customers. What sort of teams would you recommend use Calendly? Any ideal buyers?
Calendly is a tool that’s meant to be very flexible. While we do really well within certain use cases and verticals, it’s not a tool that’s limited to only those. Right now, my team mostly focuses on sales and marketing teams, customer success teams, recruiting teams, and education teams.
About ideal buyers, I think it depends because it’s usually going to be at a director-level when you’re talking about purchasing Calendly for a team. Ideally, we need to be connected with someone who has decision-making ability to decide that they would like to purchase and implement Calendly for the team.
“Powered by Calendly.” This caught onto our circle pretty fast. How big of a catalyst was it for Calendly?
The best part about it is the way it works — through simple word of mouth. Somebody would send you a Calendly Scheduling link and you may have never heard of Calendly, but you schedule the meeting and realize how easy it was to schedule that meeting. So easy that you should use the tool for yourself. From there, you’re prompted to set up your own account and you get to start using Calendly ASAP.
That is probably where the largest portion of our customers came from — simply by that viral effect.
Tell us what has worked well towards the success of Calendly. What would you attribute as reasons?
We’re a product- and customer-driven company, and our goals align with that. We want to have the best product in the scheduling space and we continue to prioritize customer feedback at every level in the company.
We are constantly asking, “what are our customers asking for, what are they not asking for, what do they like, what do they not like, what challenges are still out in the scheduling space that Calendly can help solve?” The customer is always at the forefront of every decision we make.
Every decision that we make is based on how it impacts our customers and that’s down to the details of what we do as a company. I think that that’s how Calendly itself has had so much success. I also think we have a really great team.
The talent we have here is super eager, smart, and very skilled in every department and role. They are all passionate and driven about the company being successful.
On the sales side, I would say it definitely took some time for us to build a successful sales engine. When I started a few years ago, there was nothing built for direct sales. And that’s why they brought me on board; they needed that help.
We established general sales best practices, implemented a CRM tool, and standardized processes that relate to the entire customer experience.
“But it took some time — creating the right process for us has been a game changer and it definitely did not happen overnight.”
It took a lot of trial and error, and the humility behind it all kept us going. Things like admitting to ourselves, “this isn’t working, let’s pivot.” And if we make a mistake, we choose to from it and move forward quickly, rather than try to hold onto something that we knew wasn’t working.
Calendly is a leader on G2 Crowd. How do you differentiate yourself from the competition?
I think any time that you create a tool that has the success that Calendly has, as quickly as we have, it’s bound to happen. There are definitely going to be other companies that say, “hey, I want to have a piece of that pie.” And you will start to notice that other competitors are popping up all over the place.
The feedback we get from our customers on how Calendly compares to other scheduling platforms is mostly around the platform experience and end-user experience.
Another advantage is that Calendly has been solely focused on making the best scheduling tool from day one. Other scheduling tools may specialize in certain verticals or have built a scheduling component within another software platform but they don’t really spend all of their time making the best scheduling tool.
At Calendly, we are completely focused on building the most innovative scheduling tool in the market. We are always staying ahead by listening to our customers.
Another way Calendly outperforms its competitors is our team functionality. It is a really big differentiation as it enables more than one person from a company to be part of scheduling in different scenarios. While some scheduling tools do offer that, they don’t function as well as Calendly. At least that’s what our customers have told us when they have made the switch from another platform to ours.
Calendly is a must-have tool, considering it solves the problem of back-and-forth emails. While it’s difficult to come up with a sales objection, what’s the biggest pain point you’ve faced selling Calendly?
That’s a good question. There’s not typically an objection — more like an issue of timing. And then also making sure we’re connected to the right people who can make the decision to implement the tool for their team.
This is a tool that is a need-to-have once you use it. It’s a tool that makes you think to yourself, “how have we been functioning without a tool like this all this time?” But at the same time, automated scheduling is somewhat of a relatively new concept.
So when we’re working with really large organizations or traditional organizations that are not as progressive with their technology, this is one of those things that come up.
One of the most common questions my team faces is, ‘Why are we spending money on a tool that accomplishes we can do on our own?’
This is more of an indicator that we need to focus a bit more on presenting the true value of Calendly specific to that team. The tool itself is great. I mean, we get feedback all the time — it’s simply a great tool to be selling. It’s just mostly about navigating the process correctly and aligning ourselves with the right people to get the opportunity closed.
Do you have a mission or motto that your team swears by?
Not a motto really but our team is 100% numbers-oriented. You are your quota and your numbers are your top priority.
So when we’re looking at time management and things like that, I always encourage my team to look at the thing that’s pulling them away from other tasks and ask if that activity is going to help them hit their number. If the answer is no, then that needs to be communicated and we just need to come up with a way to work around it.
I’m really big on efficiencies. When you’re working in a really fast-paced, high transactional sales environment, you have to be very careful with your time and how you manage it. The goal is to always make sure that your customers feel like you’re listening to them by staying in touch with them and providing the resources they need.
We are always asking ourselves, ‘Is this what I need to do to move the needle and hit my number?’
In your opinion, what is the most misguided practice in sales today?
It’s really tempting to get on a call with somebody and want to just show them your product. It would be very easy as a sales rep to tell yourself, “this customer has expressed a lot of interest in my tool and since they are this particular title, they are probably interested in X, Y, and Z.”
As tempting as skipping a discovery call is, I do believe that the majority of any opportunity that you have, whatever the scenario is, your likelihood to win it is made during your discovery conversation.
And that does not have to be a 30-minute to hour-long call. You can ask discovery-like questions throughout a demo so you don’t feel like it’s just a rapid-fire Q&A.
That said, there are still a ton of sales reps who take the mindset of “my product’s the best in the industry, everyone loves it, I’m going to show it to you and you’re going to love it too,” and I think that’s a slippery slope.
It’s a very dangerous path to go down for numerous reasons. One, you don’t know what your prospects care about, so you’re showing a bunch of features just hoping that something resonates. And two, you’re not being consultative, which makes your customer feel like you don’t care about their needs.
You’re just saying, here’s my product and all of its features which is just really painful to a buyer. I’ve been this exact customer when I’m evaluating tools for my team.
When people don’t take the time to just understand our basic needs and process, and how their tool all fits into that, it just definitely leaves a bad taste in my mouth.
So how do you make sure that doesn’t happen with your customer?
I think it’s really important to set the agenda at the beginning of each conversation. The whole purpose of the first call is to ask those discovery questions and truly determine if our tool is the right fit for our customer’s needs.
I always want us to tell our leads up front: “I have a couple questions for you. This will help us understand how your team would use Calendly, where we could fit in, what your goals are, what your challenges are, and then if it’s the right fit, we can jump in and show you a demo and we go from there; does that sound good to you?”
And in all the years I’ve been in software sales, I’ve never had somebody say, ‘No, I don’t want you to ask me questions about my team.’ People love to talk about themselves.
I think it’s really important to explain things up front and just make sure everybody’s on the same page.
You mentioned your team is growing. As a sales leader, what do you look for while hiring?
“I think that being humble is a very respectable characteristic that anybody can have in any role, and you should always have an appetite to learn.”
A lot of times when I have interviews with candidates, I think what happens is that they want to come across as super confident — which you do look for in a sales rep, right? You don’t want to hire somebody who’s really unsure of themselves on the phone and can’t handle rejections and the unglamorous parts of selling.
So while I do look for that confidence, unfortunately, people take that a little too far sometimes. I think that being able to say, “hey, I have experience with that and I’ve learned a lot with that but there are still a lot of things that I want to learn and do to grow” is valuable. To have that growth mindset is something important that I look for.
I think when you decide you don’t want to learn anything new, or that you have everything figured out, that’s when you hit a very dangerous place. The world is continuing to evolve and thus, the old adage — change is the only constant.
Just say, ‘I have some experience and I have a lot to bring to the table but I am also eager to learn more, take on new skills, and face the challenges.’
Obviously, I also look for a certain level of experience. This is a very fast-paced, high transaction environment and we would be doing a disservice to somebody who had never sold at all, to come in and put them in this complex role.
Also, teamwork mindset is something I definitely look for, someone who can say, “I want to be at the top of the leaderboard but I want to see everybody else succeed as well.” As a growing company, we look for employees that have more of a company mindset rather than an individual mindset.
I’m really big on that because I think that the best salespeople are the ones who have the skills and experience they need to be successful and have figured out what works for them to hit their numbers. When they know that sharing that information is not going to take that success away from themselves; it’s only going to help the team, then that is someone I want on my team to help Calendly get to the next level.
What would be your advice to someone who wants a career in sales?
First and foremost, they need to figure out and identify what type of sales they want to be in. It takes time to rise up the ladder, and you don’t want to be jumping around from pharmaceutical sales to beverage sales to medical sales to software sales because a lot of the skills are different in every industry.
Once you’ve established that, identify the companies you want to target. From then on, just be humble and know that you have to start from scratch. It’s going to take time and a lot of hard work.
I think one of the biggest mistakes a lot of people straight out of school make is they think oh, I have this degree in business with some marketing experience and I can be a sales rep, and that’s definitely not the case. You will fall flat on your face if you haven’t had some relative industry exposure along the way. Putting in the sweat equity up front is really important for any Sales Development Representative (SDR).
Your favorite productivity hack
A lot of people think that you need to purchase additional third-party tools to automate processes, and sometimes you do. But with the right tool, if you have somebody who’s skilled enough to build automation processes and workflows within a product, then it can be a big game changer.
What metrics do you focus on?
The most important metric I’m always monitoring is quota attainment. This is how we define success as a sales team. In addition to that, I also look at the classic activity metric: activity leads to success. While I’m not as much of a stickler as bigger sales organizations, I do look at how it correlates to our numbers. It tells us how we can win more deals and how we can improve our processes.
It’s more about how much of our time are we selling versus doing tasks that can have better processes.
Any recommendations for sales must-reads?
I’m more of a hands-on learner. But I do love reading blogs. I think LinkedIn is kind of overlooked in a learning capacity with people using it more as a networking tool. So it’s LinkedIn, Sales Hacker, HubSpot — there are a lot of companies that publish great content that’s just really helpful.
Freshsales is a sales CRM built to help you stop juggling multiple tools. It’s ideal for small businesses and refreshing for enterprises.
While there is no silver bullet for success in sales, there are tried and tested sales strategies so you won’t have to reinvent the wheel. Secret Sauce to Sales by Freshsales features top sales leaders across industries and gives you access to their sales methodologies. Drop us a line in the comments or shoot an email to email@example.com with your suggestions.
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