How to Use the Calendar-First Sales Engagement Approach to Rake in Revenue in 2021

With the progression of today’s marketing and sales technology, having sales reaching out to a cold list should be a thing of the past. If there has been no awareness, intent, or engagement between a prospect and your company, you’ll want to start there. Marketing should be filling this gap for sales. 

So when we hear people say, I would NEVER accept a meeting invite that was just sent to me out of the blue–good! “Stranger Danger” is real. I’ll bet that invite also has no context, a generic subject line, and no agenda… Double Stranger Danger!

However, sending a tailored and timely calendar invite is a more frictionless experience for:

• Demo request/Contact us/Free trial
• Qualified lead (MQL) triggers an inbound action
• Renewals & QBRs 
• Highly engaged target account browsing your high value webpages
• High-intent campaign: booth scan, webinar attendee, PLG engagement, case study download

Here’s an easy to follow blueprint from TOPO/Gartner’s 2021 Sales Kickoff Summit.

For the lead sources listed above, the traditional method of lead chasing with 15 step 14 day sales activity sequences don’t scale and don’t convert nearly enough pipeline. 

Lead chasing these high value leads also cause two key issues for your potential buyers:

Issue 1:
Buyers have to sit back and wait for an SDR to randomly catch them on the phone or in the email. 

Issue 2:
Using calendar comparison tools during lead chasing leaves all the work on the buyer!
1. Open the reps calendar
2. Open your calendar
3. You (Executive buyer) is required to find a time that works for the rep
4. Select a meeting type from a list of options the rep sets up
5. Fill out a form, with a description of what to discuss (even though you were emailed the link)

 

If our potential buyers (typically Directors/VPs/CSuites) are willing to follow this process to book a call with a seller (many times an SDR), sales and marketing would be a whole lot easier than it actually is.

Can you imagine how amazing it would be?
Step 1: send email
Step 2: wait for potential buyer to book a meeting around your schedule

So remember what our parents told us. Don’t accept cold invites from strangers!

What happens when someone attends a virtual event, downloads a piece of low-funnel content, or requests a demo? If your revenue organization is like most, they qualify the lead and, if it passes muster, assign it to you or one of your colleagues. Then, it’s on you to reach out to set up a time to chat. 

And thus begins a painfully slow and frustrating dance we like to call “the infinite back-and-forth email nightmare.”

If you’re lucky, the contact is highly responsive and immediately shares their availability. Or, if you use a passive scheduler, perhaps they’re proactive enough to choose a time. But, in most cases, it’s a much more arduous process that demands several emails, polite reminders, and tedious time zone math. And the further you get from the moment the lead came in, the colder it becomes.

But what if you didn’t have to play hours of email ping-pong to land a meeting with a hot lead? What if you start with calendaring the meeting?

This is what we like to call the calendar-first sales engagement approach.

 

What is the Calendar-First Approach?

The calendar-first approach is a strategy in which you send your lead a calendar invite first, rather than asking for their availability or putting the onus on your contact to choose a time from your availability.

I know what you’re thinking: “Isn’t that a little presumptuous?” 



Sure, the calendar-first approach is undoubtedly bold, but it’s also efficient and highly effective. Remember, your lead took an action that suggested they’re interested in your offering, and your organization qualified them as ready for sales engagement. They’re expecting you to do something. You’re merely eliminating a few unnecessary steps and saving their precious time (as well as your own). 



Bottom line: If you’re comfortable asking for a meeting but not ready to put a meeting on the calendar, should you be asking for their time at all?

Instead of asking your lead to sit down, review their calendar for openings and respond to you with their availability, you boil the process down to a simple choice: Accept, decline, or suggest a different time.

Of course, it’s crucial you handle the calendar-first approach with grace. 

How to Use the Calendar-First Approach to Land a Ton of Meetings

The calendar-first approach works. (Seriously, we have the data to prove it). But only when it’s done right. There are a few steps you need to take to make sure you’re increasing your chance of earning a response:

Step one: Put together your calendar invite and be sure to include a thorough agenda. (Psst: Here’s everything you need to know to put together the perfect meeting invite.)



It’s essential you fully communicate your value in your invite. What can your contact expect to learn or get out of your time together? The clearer the value, the more likely you are to earn a response.

Step two: Compose a straightforward and concise email to let the contact know the calendar invite is in their inbox, and allow them to suggest a different time or ask additional questions.



Hi Abdul,

How does 12/15 at 10 a.m. work for your demo?

I’m really excited for you to see our software in action.

I sent you an invite and included a brief agenda as a starting point. I’m happy to make adjustments – just let me know!

Thanks!
Beatriz

Step three: Send your invite and email.

The beauty of this approach is that it allows you to skip the initial round of irrelevant introductory greeting emails, helps get a meeting on the books faster, and reduces the chances of your email falling into a black hole. By taking action and simplifying the decision-making process for your contact, you’re streamlining the entire experience. 



If the contact chooses to accept, they don’t need to do anything else. If they decline without comment or ignore you altogether, then you might choose to follow-up. And if they suggest another meeting time, you can accept it, or, if it doesn’t work for you, respond with another option. No matter what, you’re getting the ball rolling.

At first, using the calendar-first sales engagement approach may feel odd. After all, most sales pros have grown accustomed to sending multiple emails before scheduling a meeting. But remember, by taking this approach, you’re doing your prospect a favor. By boiling down the entire back-and-forth to a single click, you’re helping them get value faster — and you’re eliminating headaches for yourself, too.

Want to save even more time? Automate your calendar-first approach with Kronologic. Schedule your demo to learn how:

No matter your industry or role, 2020 has been a turbulent year rife with new and unexpected challenges. But for sales development leaders, who rely on team cohesion and a motivated workforce to meet ambitious revenue targets, it’s been especially difficult.


Like many leaders over the past several months, Informatica Sales Development Group Manager JC Otero guided his newly remote workforce through corporate restructuring and layoffs, evolving customer expectations, and other transitions against the backdrop of an unrelenting pandemic.



But, in a time when you’d expect morale to fall to an all-time low, JC’s team beat their previous records and pulled off their best quarter ever.

We sat down with JC (virtually, of course) to learn how they accomplished this feat and what advice he has for other leaders facing similar obstacles.

Kronologic: Tell me a little bit about your role and your team.



JC: Informatica is a global company, and we have a pretty large sales organization of about 1100 people. I started in March 2018 as an individual contributor — first in enterprise and then strategic accounts — and helped grow our inside sales team.  

Last summer, I was promoted to sales development manager and tasked with building the sales development department from scratch. We quickly onboarded 26 sales development reps, and, for many, this was their first job out of college. These new sales pros needed a significant amount of training to prepare them for prospecting in our complex market. My goal has always been to make them the best hunters of all time.

Kronologic: Like many sales leaders this year, you’ve grappled with layoffs, turnover, and losing top performers to opportunities inside and outside your organization. What did this look like for your team?

JC: Like most companies, we started working from home in mid-March. That came with some challenges, but we still ended Q1 as our best quarter, then topped it in Q2. Then, at the beginning of Q3, in mid-July, our executive leadership announced a reorganization.

We had to let several reps go, which was a pretty big shock to everyone. Not only was this the first time many of these reps had experienced corporate layoffs, but, even as a nascent team, every quarter was our best quarter. We were very successful, yet we had to let go of a large portion of our team — including reps who hit 100% their previous quarter. People were understandably confused. Luckily our CEO did a good job of communicating the “why” behind the reorg, but it was still a tough time. 

Kronologic: What sorts of challenges did the layoffs and restructuring cause, and how did you address them?

JC: What we do is not a transactional sale; it’s a very complex sale. So, it takes a lot of time, energy, and other resources to develop our reps, especially those who don’t have as much sales or data management experience. Losing these reps after all our hard work was, of course, disheartening.

But my primary goal has always been to make them the most badass sales hunters, even if they leave and go elsewhere. It was important to make good on that promise, both for the reps we had to let go and as an example for the reps still on the team. So, I gave referrals, helped people get interviews, and held mock interviews, and within two or three months, almost all the reps we let go found new jobs. 

Also, amidst all this, we changed the segment we supported, which poses its own challenges. That meant the SDR team had to get to know a whole new group of reps and quickly putting together new go-to-market plans. So that took a lot of encouragement. I just reminded them this was our moment to shine — to prove we were masters of the hunt. The team accepted the challenge and each new quarter we’re pushing ourselves to new heights.

Additionally, because it was many of my reps’ first time experiencing corporate layoffs, they were concerned about the uncertainty. A lot of them were thinking, “I’m working from home, and there are massive layoffs — what am I going to do?” So, one of my biggest challenges was shifting the mindset.



Luckily, I’ve been through this at previous companies and in different economic cycles, and I know transparency is critical in those moments. I didn’t want to brush things under the rug, so I held a town hall with the team to clear the air and address any fear or concerns. Then, we got to work re-transforming ourselves.



Kronologic: The layoffs happened at the beginning of Q3, yet it was still your best quarter to date. To what do you attribute that success?

JC: I’ve spent most of my career as a rep, so I understand what they’re going through. And I try to be the leader that I would want to lead me in times like these. Those crucial conversations make a big difference — we are all living in this new normal, and the reps needed to understand leadership wasn’t making these decisions lightly. We couldn’t focus on things solely from an individual perspective. We had to move forward as a team.



And because we did, we hit 99% as an SDR team in Q3 for our first time ever. We also had our first promotion – a rep was just promoted to an inside sales position.

One of our team sayings is, “We always have to be ready, so we don’t have to get ready,” and it’s a mindset I’ve been working to instill since long before the pandemic. So when COVID-19 came around, that was our test and we aced it as a team.

In other words, I think a lot of our success is because of the culture we put in place beforehand.



Kronologic: What advice do you have for other sales leaders experiencing similar challenges?

JC: First, culture is everything. Since March, we’ve experimented with all sorts of things to drive team cohesion. We do morning or afternoon huddles, mid-day coffee breaks, virtual team happy hours, and hold monthly competitions. We play games not only to have fun but to allow everyone to bond and get to know each other better. This fosters a sense of support where people want to help each other succeed by sharing best practices.



Second, keep in mind that attitudes are contagious, and mindset is everything. Your biggest enemy is the voice inside your head. As sales leaders, our responsibility is to our reps, and I need to remind them that we’re in a good position right now. Despite the uncertainty, there are a lot of opportunities out there for all of us. I coach my reps to network and meet with inside sales managers as much as possible. I remind them that the better they do now, the more likely they’ll be top of mind the next time there’s an opportunity to move up.

Third, as a leader, it’s crucial you’re being as proactive as possible — like working with marketing and product groups on targeted campaigns that focus on specific solutions. And look for new opportunities for your team, like new technologies that help solve challenges you’re facing today so you can be that much better tomorrow.



Finally, remember all we can control is how we spend our time and there is always room for 1% improvement.

Want to grow your pipeline without growing your sales development team headcount? Schedule your demo now.