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Hunter Montgomery on Sales Management Best Practices and Strategies for Wooing Prospects

On effective sales management…

 I never ask my team to do anything that I wouldn’t do and I lead by example. When I was leading enablement, I was often in a weird spot where I was indirectly managing the AEs and SDRs. In order to connect with them stronger as a cross functional partner, I would give positive examples rather than just point out the things that needed improvement. If I saw a campaign that I thought wasn’t personalized enough, rather than just say, “Personalize it,” I’d write out the email myself to model the best approach.

Showing people the right way to do something is far more effective than just saying, “That’s not right.”

On building trust with my team so we can exchange honest, constructive feedback…

 Communication is crucial. If team members aren’t doing things the way I need them done, or if I think they can position themselves more effectively, it’s on me as a manager to speak up. If I’ve built enough trust with my team, I can do that without hurting feelings and causing issues.

Likewise, it’s important for me to get feedback from my team because I need to keep improving, too. Manager quality is a big factor in retaining talent. I tell my people, “Look, if there’s something you need that you’re not getting, if there’s something I’m doing that you don’t like, let’s talk about it.”

On standing out from the crowd while prospecting…

These days prospects are flooded with connection requests from salespeople looking for “just 15 minutes” of their time. I’ve found that if I first differentiate myself by establishing a level of trust, engagement and relevance, I have a better chance at getting a response. I show prospects that I understand their business and their needs. I also demonstrate that I’m patient and selfless enough to engage with them even if they don’t end up buying my product.

Following them on LinkedIn works well. I don’t need permission to follow and I can see all of their activity—what they’re posting, liking, and commenting on. I engage with them by replying to their comments, adding to a discussion on their posts, or maybe even offering a differing opinion. Then I reach out to them. If they’ve seen me four or five times they are much more likely to connect with me.

On providing outstanding customer service before the sale has even closed…

In a successful organization, departments talk to each other from pre-sale to post-sale. Customer success should start in the beginning of the sales cycle. I want customers to understand early in the pipeline what I can and can’t do for them and the potential challenges. It’s important to communicate honestly about progress and problems throughout the entire process. Proactivity is crucial. I would never inform the customer of a problem after the fact and then apologize or offer a discount. The customer needs to trust me as a business partner so transparency is key.

On making a strong first impression with onboarding…

New employees might not remember everything about the hiring process, but they will definitely remember how they felt that first day—how they were greeted, if things were organized. I put myself in their shoes by thinking back to when I was a first-time employee: what did I need or wish I had? At Workday, we survey new hires throughout the onboarding process, regularly asking, “How was this experience? How could that be better?”

On creating a diverse path for different types of learning…

In training, I think it’s important to give hires an organized—and blended—path for learning and getting acclimated to the company’s ecosystem, customers and partners. We all learn differently. Some people learn best from videos, some from live instructors, some from evaluation and assessment. Others need to upload pitches. Having a platform that accommodates all those approaches is key, especially on the sales side.


A big thanks to Hunter for chatting with us and sharing their best practices. 

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