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  • Writer's pictureMark Valdez

Software Productivity Tools with Calendly CMO, Jessica Gilmartin

Editor’s Note: This week we are excited to have Jessica Gilmartin join us to discuss modern software productivity tools. Jessica has nearly nearly two decades of B2B and B2C marketing experience and is currently the Chief Marketing Officer of Calendly. Prior to Calendly, Jessica was Head of Revenue Marketing at Asana, where she spearheaded demand generation, marketing operations, and product and sales-led growth business integrations for the Americas, EMEA, Japan and APAC businesses.

[MV] There are a crazy number of productivity apps for small businesses today which is incredibly empowering but also makes discovery quite daunting. What do you look for yourself when evaluating productivity apps? What criteria should small businesses use to ensure they find the right fit for them?

[JG] There are indeed a huge amount of valuable productivity apps out there, so it’s hard to figure out what will be critical for your business and what might become “shelfware” -- software sitting on the figurative shelf collecting dust. First, I’d suggest spending time with your team understanding the points of friction or cumbersome workflows. What's taking up more time and effort than you think it should? Alternatively, it could be where you see the biggest opportunity.

Take sales for instance. If you’re inbound focused, maybe it’s getting customers on your website to convert to leads. If you’re outbound focused, maybe it’s boosting prospect response rates. Or maybe it’s measuring sales productivity. Take the biggest opportunity you have, find the software that fits that need the best, and focus on implementing that successfully and measuring results before moving on to the next tool to implement.

Often, this does not need to be a major system overhaul or implementation. There are lightweight tools that may complement your existing systems. For instance, there are a number of tools that can help your reps save time on prospecting, sales calls and follow-ups so they can spend time where it matters most. Most importantly, for this category of productivity tools, ease of use is critical, otherwise the software will end up making you less productive rather than more!

[MV] It strikes us that the best productivity apps do more than just save you a few minutes each day. In fact maybe "productivity" undersells the category and it should be more like "business growth apps." How should business owners think about what productivity apps can mean for their business?

[JG] You’re absolutely right. Productivity apps can do with a marketing makeover! Any technology you purchase should help you achieve a significant and demonstrable business outcome. If you purchase a productivity tool for your recruiters to help them schedule candidate meetings more efficiently, you shouldn’t measure success by recruiter time saved (although that’s a nice bonus) but in getting more candidate meetings scheduled faster so you can hire the best talent. So, whether it’s increasing sales, decreasing costs, or improving customer satisfaction, that’s the value you should be looking for in a productivity tool.

[MV] Nearly every modern software app (at least the good ones) comes with APIs that provide integrations between applications, but the power of APIs is not always well understood. Part of what makes Calendly so special is its API and the ability to integrate or embed Calendly with other apps. How do you all help small businesses understand the power of APIs and the art of what's possible?

[JG] Since my team alone uses over 50 individual apps, I can personally attest to how important it is for the different pieces of your tech stack to speak with each other. APIs are critical to support 2 key workflows:

First, they allow you to see your data in one place and allow you to see a full story of results and impact. There’s nothing more frustrating than having to piece together data from 5 separate tools to understand your candidate acceptance rate or your lead to closed won conversion rate. Yet that’s what many of us are forced to do when we have tools that don’t connect with each other.

Second, APIs enable teams to stay in the tools they’re already using. Salespeople are in Salesforce all day, every day. Asking them to switch between 10 different platforms to get their job done wastes time, makes them frustrated, and reduces the chance they’ll use the app you just spent good money on! So in this example, if you want a salesperson to use it, make sure it’s part of their existing workflows in the tools - like Salesforce or email - they use most heavily.

Calendly's API is an important part of our own customer value proposition as it allows teams to be creative in how they add a Calendly landing or booking page to their own website by enabling one of three embed variations: inline, pop-up text or pop-up widget. We want to empower our customers with Calendly's capability in the way that works best for them.

[MV] While Calendly started as a scheduling tool, there is a lot more capability that comes from the Calendly service. Talk about how you all approach product development and product marketing to enhance your customer experience and value proposition.

[JG] Of course our product development always starts with our customer. We look very closely at not just who buys Calendly, but who gets the most value from it. So which types of customers (by size, function, level) are most likely to remain paying customers over the long term? Who requires more complex scheduling automation, which increases stickiness? What are our target customers’ existing critical tools and how can we integrate with those to provide a seamless experience? What new features are our customers requesting that we believe will drive additional business value? These are a few of the ways we think about our product development, and when we launch new features to the market, we focus on how we share the use cases and value of these features, vs. just describing the features themselves.

[MV] Lots of apps will show traction with early adopters, but fewer actually cross the chasm to mainstream adoption. What is it that sets those apps apart?

[JG] I mentioned this earlier, but one thing we hear all the time is that ease of adoption is critical. The bar is way higher for technology than it used to be, and B2B product leaders have had to learn a lot from B2C products on how to create a delightful first time user experience that is intuitive, fast and simple, even when they’re solving complex problems. If it’s not easy to understand, no matter how powerful it is, your product won’t get adopted.

Another critical factor to success is being customer-centric at every level. As an example, at Calendly we know you’re going to use our product to interact with people - whether that be candidates, prospects or customers - that are important to you, so we focus on creating a seamless and delightful experience for them as well. That trust you build with your customers by being responsive and attuned to their needs will drive their loyalty and adoption.

[MV] Other than Calendly of course, what are some of your favorite productivity apps?

[JG] My last role was at Asana and it is still my absolute must-have project management tool in my productivity toolkit. I can’t imagine going back to a world of email and spreadsheets! Asana is great at keeping my team aligned on tasks and objectives. At Calendly we frequently use Loom videos to share asynchronous information, which I’ve really come to appreciate since we are fully remote and we’re able to disseminate complex information more quickly via video. Otherwise, I basically spend 90% of my working life on Zoom, Slack and Google.

[MV] Thanks for sharing your insights with us, Jessica!

[JG] Of course, thanks for having me.

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