Enterprise Sales - Key lessons from 9 Executives

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What I learnt after interviewing 6 AEs, 1 Sales enablement, 1 RSM and 1 VP.

There are senior Sales reps with 20+ years, as well as the younger generations who rapidly move up the ranks.

Key lessons

1, Sales = Art + Science. 

  • Art -  To find common grounds and points of interest quickly. Empathatic.

Keen sense and critical thinking to read the dynamics if things are moving or “not really”, despite what they may appear at the surface. 

Listen intently - what is the compelling event? Is the need a “Must”, or nice to have? What’s the consequences of doing nothing? The VP commented, listening is a key trait that differentiates good reps from the average.

  • Science - have a system to prospect, document notes, set expectations and follow through.

This will help you forecast accurately - critical to the sales manager you report to as well as building individual credibility and momentum.

*Contrary to conventional thinking, the “Art” part does not require “years” to acquire. Sales are street-smart. If you are intentional, you would have been practicing these foundational soft skills daily and see relationships flourish.

2,  Prospecting - most important and most difficult.  

  • As many reps pointed out - Most sales would still struggle at calling and prospecting. SDRs are doing the most difficult part of sales. Once the connection is made and needs mapped out, the rest often will move forward organically.

  • Have a pipeline 4x the quota is the key to attainment.   

  • Create a reward circuit that celebrates sowing seeds over harvesting. 

3, Qualify opptunities in/out quickly.

  • Use a framework like MEDDPICC or good old BANT in depth.

  • To qualify well, get an org chart and engage as many stakeholders across the decision hierarchy to get the big picture and to validate assumptions.

  • Most importantly, understand who the “Economic buyer” is. Ultimately, if the solution cannot justify their spending metrics (by certain $$ or % ROI), all the good effort can be vetoed.

4, Levarage the extended sales team to maximise your reach and efficacy.

  • External - Partners, industry contacts, social platforms where you can share insights and interact.

  • Internal - Engineer/presales, inside sales and Executive-level influencers. for eg. at Tenable there is a Chief Cyber Strategist who is ex CISO for big enterprises, and SMEs in industrial security.

5,  Coachable, consistent, and the hunger to improve.

  • As the competitive landscape is getting more volatile, these traits are more important than ever.

  • A few reps argued most of the other skills/tools can be trained up in a few weeks by an experienced sales manager.

But not these.

  • Are you a winner who has a big “why” that forces you to be malleable in realising one’s potential? Who has higher places to go to so each opportunity must be seized to build credentials?

  • Or, can you be “bought” by a certain number of achievements, money and comfort?


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Why I excel at Sales (MEDDPICC notes) - pt1

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$$$ Sales method - Command of the Message in 9 mins