#157 Enterprise Tech Sales Appointment Setting Playbook (live cold calling roleplay)

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In this episode, I sit down with Brandon Jackson, SDR and outbound leader at Common Room, to break down what effective enterprise outbound looks like today.Brandon walks me through a live enterprise cold call and explains the preparation, research and psychology behind each part of the conversation. We also discuss how to qualify meetings properly, build quality pipeline, create effective multichannel cadences and develop stronger relationships between SDRs and account executives.

You’ll learn:

• How to open an enterprise cold call with relevance

• Why preparation matters more than memorising a script

• How Brandon qualifies opportunities using the CANT framework

• What helped one of his SDRs achieve a 10 out of 10 meeting show rate

• How to use calls, email and LinkedIn together

• How SDRs can build their internal brand and progress into bigger roles

Whether you’re an SDR, account executive or sales leader, this conversation is packed with practical lessons you can apply to your outbound strategy.

Timestamps

00:00 - How to open an enterprise cold call

02:45 - Enterprise sales vs commercial sales

06:07 - Why enterprise selling is an art

09:26 - The $1.8 million commission cheque

12:15 - Preparing for a live enterprise cold call

13:45 - Live enterprise cold call roleplay

18:15 - Breaking down the cold call

20:50 - Why preparation creates better conversations

24:42 - The three outcomes of every cold call

27:24 - How to build quality pipeline

28:47 - The CANT qualification framework

31:17 - Developing SDRs into future sales leaders

35:21 - How an SDR achieved a 10 out of 10 show rate

39:21 - Building strong SDR and AE relationships

43:41 - Using Outreach and AI for prospecting

45:00 - Building an effective multichannel cadence

47:43 - Why the first six touches matter most

50:40 - Personalisation and long-term follow-up

55:26 - The mindset required for cold calling

57:18 - How to 3X to 10X your sales career

59:41 - How your life can change in six months

ABOUT ME:

I help B2B tech companies build world-class outbound sales teams through training programs, workshops, and sales kickoffs. Former seller at Oracle, Google, & an AWS partner who has coached 100s of reps across the industry to hit quota & unlock their personal potential.

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