How to develop a winning sales strategy

1 min read

Kent Holland

Kent Holland leads Copper’s Global Sales Organization. Prior to Copper, Kent was a business development leader at Box, helped drive new product launches and sales strategy at LinkedIn, and started his career in the strategy and operations consulting practice at Deloitte.

Kent was featured on our Limitless webinar series on February 11, 2020 at 11 AM EST. He had some really great insights to be shared on developing winning sales strategies.

Watch the complete webinar:

Time-Stamped Show Notes:

[04:37] What are the key factors to develop the winning strategy?

[25:14] How do I know the target market is resonating with my audience? 

[33:20] How do you build a sales team with culture?

[44:25] What is the playbook Strategy?


Question: What are the key factors to develop the winning strategy?

Kent: If you’re not thinking about developing and refining your sales strategy every three to six months as the market changes, new tools come out, etc., then you’re going to be falling behind. 

Question: How do I know the target market is resonating with my audience? 

Kent: This is a tough one because you never. Assessing product-market fit and sort of the fit that you’re sort of ICP messaging has with your target market. It can be very tricky because there can be signals that are misleading all the time. But, you know, and it’s sort of the high level what your guidepost should always come back to setting up the right KPI.

Question: How do you build a sales team with culture? 

Kent: I think getting a sales team culture right is tricky, but it’s one of the most important things you can do. And every team culture is going to be really different. it’s really important to do a couple of things. I think one is to drive the sort of team camaraderie and make sure folks stay connected. That encourages them to stay connected with each other and to the business.

Question: What is the playbook Strategy?

Kent: Anything I would look at, I would start with an understanding of what the key milestones are in that process from the top of the funnel through to current customers and beyond, including sort of onboarding activation and ultimate expansion of that customer. And I want to understand from both a revenue and a logo perspective how our prospects and customers progressing through that funnel, that’s going to then give me an understanding of where there’s opportunity to improve based on what’s in place.

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