November 10

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Entrepreneur’s Guide To Hiring A B2B Head of Sales

By John Conrad Lee

November 10, 2021


Are you an Entrepreneur or business owner selling to B2B clients? As a startup, one of the biggest challenges you’ll face in business is hiring a Head of Corporate Sales or B2B Sales Director.

As a fellow business owner, I hope my experience from decades in B2B sales helps you make the right decisions for your company.

What Is A B2B Head of Sales?

I’ve been employed as a Head of Sales, and am now a business owner. 

A Head of Sales should be:

  • Someone you can rely on to sell when no one else can. They should be have the skills, experience and mindset to show the team how it’s done, and be able to bring in results when it matters. A Head of Slaes needs to have excellent selling skills.
  • Someone who can help the sales team get results. Salespeople are measured by results, so it’s only natural that they’ll respect someone who has themselves produced results. But the team now needs a leader who can help them bring in results. Their manager needs to help up-skill the team, to transfer their knowledge and sales expertise to the team. A Head of Sales needs to coach the team for results.

So Should I Hire A B2B Head of Sales?

In conclusion, my recommendations are:

  1. Get the best salesperson you can afford for your first hire. This will be someone who can actually prospect, sell and close deals, someone who’s willing to be a salesperson, no matter how senior they were in their previous jobs. No point getting someone who’s only willing to be a manager, because in the beginning you need sales, not management layers. This first salesperson should be someone you can depend on to start bringing in the sales you need to stabilize your business.
  2. Consider fresh graduates and interns to build up your team. They won’t have relevant experience or selling skills, but they should have loads of energy and drive. Allow them to help with sales administration, operations, customer service… the more exposure they have to the way your company works, the better they’ll be as sales people. Of course you’ll also need to provide structured B2B sales training to equip them with the right selling skills. Our B2B Sales Accelerator program is designed to help with that.
  3. Hire a Head of Sales when you have a sales team to manage. This is when opportunities in the market require a sales team, and a team always needs a good leader. This should be someone who can lead the way by selling with the team, going with them on sales calls, coaching them and helping them to develop good habits and solid selling skills. Your Head of Sales will need to develop sales incentive programs to keep the sales team motivated and coaching programs to keep them at peak performance. This is a lot to ask from one individual, and a good option is to let your Head of Sales focus on selling and team management while you engage us to take care of the team’s professional training needs. Our B2B Sales Accelerator program is designed to support your Head of Sales as they manage their team.
  4. Invest in training your sales team and see the returns in your top line. Sales training should always translate into sales results, and that’s why the best companies in the world have entire department dedicated to training. For smaller companies and startups, training is even more important, because you need to keep every talent you can get your hands on! Coaching your sales team is how our B2B Sales Accelerator program can make a direct impact to your financial results.

John Conrad Lee

About the author

John is the Founder of Waymaker Acceleron and teaches B2B Sales Excellence.

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