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The Ambitious Sales Development Team: An Interview with Sean Kester

TOPO is committed to bringing the sales development community the latest trends, data, and best practices from the fastest-growing companies in the world. Today, we continue our sales development interview series with Sean Kester, Head of Sales Development from SalesLoft. He’ll share his best practices, most impactful decisions, goals, challenges, metrics and the most effective technology his team is using today.

Dedicate 30 minutes to a 1-on-1 with each rep every week

Question 1: What decision did you make that had the biggest impact on your sales development team’s success?

Dedicating time to sales coaching and leadership growth.

When scaling a team, there is much more to understand, measure, and coach than just metrics. There is always a why.

Dedicating 30 minutes to a 1-on-1 with each rep every week at the same time no matter what had the greatest impact on the entire team’s success. Diving into the core reasons a particular result occurred allows for analysis. As a result, it’s possible to determine a solution that tackles the fundamentals of the problem and helps a rep improve.

sean kester

Connecting with prospects via phone is the biggest challenge of 2015

Question 2: What is the biggest challenge your sales development team is facing in 2015?

Phone Connections. More and more businesses are shutting down their Voicemails. For example Coca-Cola (shoutout to the ATL home team) recently turned off their entire corporate VoiceMail system at their HQ.

There is also an increased use of cellphones as primary business lines, which, coupled with the lack of easily attainable direct dial information, has made telephone connections increasingly difficult.

Strive to be the beacon of SDR best practices

Question 3: What are the Sales Development Team’s biggest initiatives for 2015?

Take over the world…well at least the sales development world.

We strive to be the beacon of SDR best practices leading all of humanity by pushing the limits of the prospecting and outreach process. To put it simply we practice what we preach, drink our own Kool-Aid, and always test new strategies to grab the attention of our prospects.

Use demos scheduled and demos completed as key performance metrics

Question 4: What are the top 3 metrics you use to measure your sales development team’s performance?

1. Demos Scheduled: How many cold dark strangers turn into warm qualified leads?

2. Demos Completed: How many of the demos scheduled show up to speak with the Account Executive?

3. Activity: How many touches (email, phone, social) did it take to get each demo scheduled?

Bonus Metric: FIFA skills. Is your game strong? (The FIFA Sean is referring to is the soccer video game)

There are 3 indispensable but lesser-known productivity tools for SDRs to evaluate

Question 5:  What technology is having the biggest impact on your sales development team’s performance?

Our Sales Development team drinks our own Kool-Aid. SalesLoft’s solutions are built for customer acquisition. They’re the fastest and easiest way in the universe to turn cold dark strangers into qualified interested demos and appointments.

Here are a few other tools we find indispensable:

Atext: A quick text tool that accelerates your typing by replacing abbreviations with frequently used phrases that you can define.

Rivalry: A sales coaching and gamification platform showing you the “what” and helping to uncover the “why.”

Birdhouse: Birdhouse emails you daily with the Twitter activity of your Salesforce contacts and other people you care about most.

Today’s author:  As the Head of Sales Development for SalesLoft, Sean quickly built, implemented, and scaled a process for the sales development team that is now the largest group inside the company. Sean describes himself as: “…driven by the desire to impact the lives of sales development professionals and passionate about the company I work for, the people I surround myself with, and to be the beacon of sales development best practices for the SaaS industry.”

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