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Sales, Training

Sales Mastership at Dreamforce 2016

Jacco van der Kooij

Written by Jacco van der Kooij

Founder, Winning by Design


This week we kicked of the Sales Mastership program for 2017 at Dreamforce in San Francisco. This event was sponsored by Salesloft, Storm Ventures and Winning By Design, our goal was to show the importance of training in the world of sales.

Importance of Training Sales Development

Training of SDRs has become extremely important. As such, we wanted to demonstrate the impact proper training can have, by putting on a workshop for SDRs, AEs, ad AMs. 108 people attended across 2 sessions from over 40 companies — which included Aria Systems, Betts Recruiting, Boomerang Commerce, Clari, DataHug, Digital Shadows, GuideSpark, Hiplead, Intact, Kentik, LeadGenius, Liftoff, RainForestQA, SwiftStack, and TalentBin to name a few.

Training Sales Development

Case in point: How to Prospect without Spamming

During Dreamforce we trained teams on how to prospect in a customer centric way while simultaneously orchestrating outreach to a client 5 times over 12 days.

Mind you that without a modern training program this quickly turns into a sh!t show of spammy emails with boring sales pitches harassing clients.

It doesn’t have to be that way.

Below a video example of an email heavy sequence in which we use; email, email, voicemail/email combo, email, email sequence.

Key principles we taught:

  • Demonstrate you have done some basic research on the client
  • Understand where your customer is on the client journey
  • Provide relevant insights and offer real value
  • Balance of hyper personalization vs. scaling your work
  • Address emotional needs early on, rational needs later on
  • Mix it up between email, phone, and voice mail
  • Don’t ask for a 15 minute meeting — this is so old! Provide value!!

Once you get the idea you can change sequences to be more social centric, more phone driven, increase amount of touches or opposite increase amount of days etc.

SDR Mastership Program

In this training session we focused on a sub-set of the overall program with the following elements:

  • A customer centric sales methodology
  • Interaction Skills; Email (RRrR), and Phone (Open, Objection, Ask)
  • Inbound plays (2 Plays: SingleTap and DoubleTap)
  • Outbound 1–1 (6 Plays: LinkedIn, 1–1, vertical, top-down, etc.)
  • Outbound 1-Many (How to create a sequence)
mastership program
Winning By Design Sales Masterhship Program for SDRs, AEs, and Customer Success

We were only able to cover a few SDR plays. Others such as Account Executives and Account Managers need similar training on modern sales.

Classroom Style Training With Break-out sessions

Over the years we found that sitting in a class room is extremely hard so we implemented the following:

Step 1: Explain the concept in a class room style

Classroom Style Training

Step 2: Break-out session to perform a (group exercise)

Break-out session

Step 3: Role play. In this example the Hiplead team is role playing taught communication skills.

Role play

I believe that proper education will solve many of the problems we are facing in many sales organizations.

Thank you!

On behalf of all the participants over the past 2 days I want to thank our sponsors Salesloft and Storm Ventures for helping us pull together this event and make a difference for 108 new sales professionals.