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Sales Coaching
May 7, 2023
Nishit Asnani
Discover unconventional methods to reach the top decision-makers in enterprise and mid-market deals. Unleash your inner sales ninja and close more deals with these creative tactics.

Why do so many sales reps feel like they're stuck in a labyrinth, desperately trying to find the elusive decision-maker who holds the key to closing a deal? In the world of enterprise sales, reaching the right person at the right time can often make or break your success. But fear not, young sales warriors, for we have assembled a treasure trove of creative methods to help you navigate the maze and reach the decision-making authority.

Networking Like a Pro

Who said networking has to be a chore? Let's reframe it as the art of building genuine connections that can lead to exciting opportunities (and maybe even some new friendships).

  1. Leveraging LinkedIn for warm introductions: LinkedIn is a goldmine for finding mutual connections, so don't be afraid to reach out to your network for introductions. Just remember, as Aunt May said to Peter Parker, "With great power comes great responsibility." Use your connections wisely, and always be willing to reciprocate when others need your help.
  1. Attending industry events and conferences: Sure, we live in a digital world, but nothing beats the magic of in-person interactions. Conferences and events are perfect for finding new contacts and nurturing existing relationships. Just remember to pack extra business cards and a healthy dose of charisma!
  1. Joining relevant sales and industry communities: There's power in numbers, and joining sales communities or industry groups can offer valuable insights and connections. Share your knowledge, ask questions, and watch your network grow.

Channeling Your Inner Detective

If Sherlock Holmes were a sales rep, he'd be a master at reaching decision-makers. Channel your inner detective and follow these steps to uncover valuable insights:

  1. Conducting in-depth research on target accounts and decision-makers: Before you reach out, do your homework. Learn about your prospect's industry, company, and role to tailor your approach and show you're not just another sales rep looking for a quick buck.
  1. Identifying mutual connections or interests: Look for common ground to build rapport with your prospects. Did you both attend the same university? Share an interest in a niche hobby? Use these tidbits to create a more personalized, genuine connection.
  1. Using social media to gain insights and establish rapport: Social media platforms like Twitter and Instagram can provide valuable insights into your prospect's interests and personality. Engage with their content, and use what you learn to tailor your outreach.

Stay tuned for the next sections, where we'll dive into the art of the cold email, partnering up with other departments, going old school with direct mail, getting creative with video outreach, and the power of the phone.

The Art of the Cold Email

If you think cold emails are about as exciting as watching paint dry, think again. With a dash of creativity and a sprinkle of humor, your emails can become the highlight of your prospect's inbox.

  1. Crafting personalized, attention-grabbing emails: Nobody likes to feel like they're just a number on a list. Make your prospects feel special by crafting personalized emails that address their specific needs and interests.
  1. The power of humor and storytelling: A well-placed joke or an engaging story can make your email stand out and leave a lasting impression. Just be sure to keep it relevant and professional.
  1. Timing and follow-up strategies for cold emails: Timing is everything. Experiment with different days and times to find the sweet spot for your target audience. And don't forget the importance of following up!

Partnering Up with Other Departments

You don't have to go it alone. Collaborate with your colleagues in other departments to create a united front and boost your chances of reaching decision-makers.

  1. Collaborating with marketing for targeted campaigns: Work with your marketing team to create highly targeted campaigns that speak to your prospect's pain points and showcase your solution's value.
  1. Leveraging customer success stories and testimonials: Nothing sells better than success. Share customer success stories and testimonials to demonstrate the real-world impact of your product or service.
  1. Utilizing connections within your own organization: Don't forget about the wealth of knowledge and connections within your own company. Tap into your colleagues' networks and experiences to find new paths to decision-makers.

Going Old School with Direct Mail

In the digital age, a physical package can make a big impression. Let's get back to basics and explore the power of direct mail.

  1. Sending personalized gifts and attention-grabbing packages: Catch your prospect's attention by sending a unique gift or package that showcases your creativity and thoughtfulness.
  1. Using direct mail to complement digital outreach: Direct mail works best when combined with your digital efforts. Use it to reinforce your message, add a personal touch, or break through the noise of a cluttered inbox.
  1. Why direct mail can still be a powerful tool in the digital age: In a world of digital overload, direct mail can help you stand out and make a lasting impression on your prospects.

Getting Creative with Video Outreach

In a world where face-to-face meetings are not always possible, video outreach can be a powerful way to connect with decision-makers and showcase your personality.

  1. Recording personalized video messages: Stand out from the crowd by sending custom video messages that demonstrate your genuine interest in solving your prospect's problems. 
  1. Leveraging video platforms like Loom and Vidyard: Platforms like Loom and Vidyard make it easy to record and share videos, track engagement, and integrate with your existing sales tools.
  1. Combining video with other outreach methods: Don't limit yourself to just one channel. Combine video with other outreach methods like email, direct mail, and phone calls for maximum impact.

Don't Forget the Power of the Phone

Despite the rise of digital communication, the phone remains a potent tool for reaching decision-makers. Here's how to make the most of it.

  1. Phone call best practices for reaching decision-makers: Be prepared, confident, and respectful. Know your prospect's pain points and be ready to offer a solution that meets their needs.
  1. Utilizing AI tools like Sybill for effective call preparation: Take advantage of AI-powered tools like Sybill to analyze past calls, gather insights, and refine your approach to reaching decision-makers.
  1. How to handle gatekeepers and objections on the phone: Be prepared to navigate gatekeepers and handle objections with grace and confidence. Remember, persistence pays off.


In the competitive world of enterprise sales, creativity and persistence are key. By leveraging unconventional methods like networking, detective work, cold emailing, partnering with other departments, direct mail, video outreach, and phone calls, you can maximize your chances of reaching decision-makers and closing deals.

Remember, there's no one-size-fits-all solution. Experiment with different tactics, learn from your successes and failures, and always be ready to adapt. With a little ingenuity and a lot of determination, you can turn those cold leads into closed deals.

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