Sell Smarter, Not Harder: The Case for Automating Your Tech Stack


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Time and distance are said to be the enemy of any long-lasting relationship. As today’s business relationships become more asynchronous and distributed, sales leaders need to find creative and efficient ways to reach prospects and win deals.

Welcome to the digital-first era of work, sales leaders. Automation has solidified itself as the digital backbone of sales team success.

It’s no secret technology has evolved to help bridge this gap and provides an edge to those who can optimize it. The proliferation of new tools provides sales professionals with both a challenge and an opportunity to assemble an effective tech stack that improves their workflow and integrates with their existing technology. Now is the time: embrace automation to speed up your sales pipeline, push prospects through the funnel faster, and create a smoother buyer journey with less friction.

Putting into Practice

50 percent of sales go to the vendor that responds first. At Calendly, we found it takes an average of seven emails sent back and forth to schedule a single meeting. Sales teams look to technology to improve their performance and reduce the time, effort, and expense dedicated to mundane, yet important administrative tasks often slipping through the cracks; think data entry into your CRM, sending meeting follow-ups and reminders, and assigning demos out to available representatives.

Let’s look at three common use cases for the modern sales tech stack.

Business Intelligence & Analytics: Collect, integrate, and analyze data at every stage of your customer’s journey and translate it into timely and pertinent reports and forecasts (e.g., tools like Salesforce, HubSpot, ZoomInfo, CallRail)

Customer Engagement & Communication: In today’s multi-channel and mobile business environment, customer communication has never been as important—or challenging. Technology can help you find the right messaging, cadence, and channels to reach and meet with your customer in a broadly distributed world. (e.g., tools like Mailchimp, Slack, Calendly)

Sales Enablement: Bridge the communication gaps you’ll find when coaching and running a remote sales team. Leverage tools to inject a personal touch while training your teams to apply best practices with customers that are scalable and repeatable. (e.g., tools like Gong,, Highspot)

Building for Effectiveness

1. Embark on an Automation Journey
The use cases above are a small sampling of the ever-growing sales tech stack marketplace. For many, this may seem overwhelming, but high-performing sales teams have been shown to take advantage of nearly three times more sales technology than underperforming teams. A 2019 benchmark study pinned the median number of sales tools used by sales professionals at nine and a spend of at least $150 per month/per user.

Sales teams have traditionally been early tech adopters and often pioneers of bringing new technology into organizations. The sooner we can blend human talent with automation to effectively tailor our tech stacks, the more efficient will be at solving customers’ real business problems.

2. Be Empowered by Tech-agnostic Integrations
In the past, sales professionals were locked into a single technology vendor’s platform, limiting their options. Today, the cloud and Software as a Service delivery model have democratized the technology space with seamless integrations and variety.

With minimal investment in hardware, fork-lift upgrades and vendor lock-ins become relics of a bygone era. Sales teams can now narrow in on the specific problem they’re facing and seek out the best-in-class tool or platform to help them solve it to get what they need, when they need it, from the best provider for them.

3. Don’t Forget to Make the Personal Connection
Despite doomsday predictions that automation and artificial intelligence will replace salespeople, the need for human interaction to be woven throughout the sales cycle has never been higher, particularly in high-touch areas like business-to-business sales. Four of the top seven sales skills—empathy, communication, humility, and emotional intelligence—can never be fully replicated by even the most sophisticated technology.

The COVID-19 pandemic and shift to a remote/hybrid work environment means cultivating trusting relationships with customers is significantly more important. A sales tech stack that seamlessly integrates tools like Zoom and Salesforce makes it easier to foster and maintain valuable relationships with prospects and existing customers, even when face-to-face interactions aren’t possible.

The Sales Tech Stack of Tomorrow

Technology will continue to evolve, and your sales tech stack will be ever-changing. Ultimately, the top-performing salespeople will be the ones who harness 21st century tools to build bespoke tech stacks and automate the long-standing problems of yesterday’s sales cycle.

Amy McClain
Amy McClain is the Senior Manager of Sales Enablement at Calendly, the modern scheduling platform for high-performing teams and individuals. She's a seasoned sales leader passionate about leveraging information, content and tools to enable sales teams to reach peak performance.


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