Defying the Odds: How This Sales Leader Elevates Cold Outreach with Proven Strategies

Kyle Rooney, Route’s director of sales, has turned the uncertainty of cold outreach into a strategic game of favorable odds and demonstrated outcomes.

Written by Lucas Dean
Published on Oct. 09, 2023
Defying the Odds: How This Sales Leader Elevates Cold Outreach with Proven Strategies
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Cold outreach can feel as unpredictable as rolling the dice and hoping for a favorable outcome. Some degree of uncertainty is unavoidable, and even with proper knowledge of prospective clients and perfect execution, there will be more noes than yeses.

Consider this: If one were to roll two six-sided dice, hoping they land on specific numbers — say a three and a five — there is a 5.56% chance the desired outcome would occur. Repeating the same scenario but with four dice and numbers, there is a 1.85% chance all of one’s chosen numbers would appear. 

That probability is ever-so-slightly larger than the success rate for cold calling, 2%, according to Zippia. Meanwhile, the average cold email response rate is 1% — equivalent to the odds of seven rolled dice producing seven chosen numbers. 

These odds demand resilience and endurance to reach the desired results. But unlike rolling dice, sales professionals hold sway over the outcome. Skill, intention and foresight don’t play a role in the hypothetical dice scenario, but are everything in cold outreach. 

By honing one’s approach to cold outreach and pinpointing what strategies result in success, sales professionals can become statistical outliers. 

At Route, Director of Sales Kyle Rooney has several straightforward strategies with proven results — an email with a 40% response rate, for instance. Rooney shared how other sales professionals can optimize their cold outreach methods. 


Kyle Rooney
Director of Sales • Route

Route rethinks e-commerce by enhancing online shopping and post-purchase experiences through a unique marketplace with millions of users and over 10,000 merchants. 


How often do you use cold outreach methods? Why and when do you turn to these methods?

Around 60% to 70% of a sales rep’s job at Route is cold outreach. Being given an account, finding an email and phone number and then reaching out to them to meet with you is the job. Any sales team using tried-and-true outreach methods is almost guaranteed success. 

In 2023, so many platforms spent so much time and money putting ads in front of you. If all SaaS companies did was throw money at these platforms and hope for results, you might run out of money before you have a substantial return. When you get a talented seller, a phone and some leads, you substantially increase your chance of the prospect getting a real education on your product before deciding if it fits their business. 

As a sales rep at Route, we encourage calendar blocking. Basically, you would schedule your day to include time for essential activities. 


A typical schedule could look like: 

  • 8:30-9 a.m.: Reply to emails
  • 9-10 a.m.: Prospecting work — find correct contact info
  • 11 a.m.-12 p.m.: Call block
  • 12-1 p.m.: Lunch
  • 1-3 p.m.: Meetings and demos
  • 3-4 p.m.: Call block
  • 4-5 p.m.: Prep for the next day


Please share a time when cold outreach worked for you. What did you do, and why was it successful?

One of my favorite strategies when doing cold outreach is using FOMO — fear of missing out. In e-commerce, the smallest details can push a customer from buying from your website to buying from a competitor’s website. 

Some of my best successes came from going down very small verticals. Once, I was chasing websites that sold drones and drone parts. The strategies were very straightforward. I had previously closed a couple of websites that sold drones and crafted a straightforward email with an easy-to-understand subject line: “John’s Drones & Sally’s Drones are using Route to get rid of Lost/Stolen/Damage issues.” 

One of my philosophies when you are cold emailing is to keep the email short. Your only goal is to pique interest enough that they will take a call with you. My email would start with, “Route is partnered with X, Y and Z websites to get rid of Lost/Stolen/Damaged packages and give the customers a white glove experience if something goes wrong in transit. Do you have 15 minutes later today or tomorrow to see how your competitor is doing that?” 


One of my philosophies when you are cold emailing is to keep the email short. Your only goal is to pique interest enough that they will take a call with you.”


I had a 40% response rate to that email. Each time I closed another drone merchant, I added their name to my cold outreach email list.


How do you use cold outreach to complement your other sales strategies? 

Cold outreach is imperative for any high performer, but another trait I consistently see in them is their ability to build relationships with prospects. If a sales rep can build a good relationship with a prospect they can feel comfortable asking, “Do you know anyone else that could benefit from our service?” at the end of the deal cycle. 

It’s a small detail, but I have seen it yield so much revenue for sellers who build relationships with prospects so they are comfortable reaching into their personal networks to give you a referral. All the work that comes from cold outreach can be cut short if sales reps are not treating each of these prospects as the big opportunity they are.


Responses have been edited for length and clarity. Images provided by Shutterstock and Route.

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