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Sales Leader Interview — Hillary Anne

The Future of Sales Management

Hillary Anne is the Senior VP of Sales and Strategic Partnerships at high-growth tech company A career sales leader, she now oversees multiple teams of managers and sellers for the conversational enablement platform.

We sat down with Hillary to get her take on management and automation in technology sales.

What do you think are the main responsibilities of the sales manager today?

In a perfect world, sales managers are there to help their team stay motivated and focused, help pull deals across, and help the team get the best results that they can. Today, I think that the sales manager job ends up also being a lot of digging for data, reporting, metrics, spot-checking, and cross-checking. Frankly, I find it to be extremely inefficient. The faster managers can get actionable data, the more impactful they can be.

What do you think the sales manager role might look like in 5-10 years?

In 5-10 years, I think great sales managers will have tools that possibly help them to run larger teams. Today, we try to keep headcounts at 8-10 reps per manager because, frankly, it’s a lot of people to pay attention to. You have to dig into their entire pipeline, read emails, listen to calls, and pay attention to where they’re headed. The more technology helps improve that process and feeds actionable data back to sales managers, the more effective and efficient they become—and they can then possibly take on more reps under their wing.

How many layers of management are best? I always wonder, how many people do you actually need in management?

How does the rise of sales automation technology impact managers?

Automation is great. We use automation here at, and we try to automate many of the things that the sales teams should be doing on a daily basis. However, sales is all about rapport, trust, and establishing relationships. So, it’s dangerous if you’re not following up automation with a personal touch. We make sure to add a lot of human touch inside our campaigns.

I think it’s important for sales leaders to pay attention to the metrics around automation. Is it working? Is it effective? Are you getting the results that you wanted to get out of it? Because if sending out 10,000 emails a day is effective, great. But if it’s not, you’re just wasting your time. The goal of leveraging automation should not be to automate endlessly—it should be used to remove friction and help your team get into more conversations where they can build relationships (ultimately improving ROI).

What advice would you give to new sales managers?

When you walk in as a new sales manager, your heart’s often in the right place, and you just want to fix everything you see. But it can be a jarring experience for salespeople if it’s not done with a little bit of finesse. It’s difficult to influence change with a person until you’re able to establish trust and rapport. If you haven’t done that, then whatever change you’re trying to make with a person just feels like a conflict to them.

Really focus on building relationships and trust, first, between you and the people you’re taking over. It’s the concept of: go slow now so you can go fast later. What does this mean? Spend time getting to know everyone before you ask for anything—yes, this can be time-consuming and won’t typically impact results today, but it will deeply impact results in the future. When you have great relationships at work, you can conquer mountains in no time.

Thanks, Hillary, for the great advice for sales managers and your predictions for the future of our function. Stay tuned for another post in the BuyerSight Sales Leader Interview Series, and check out the rest of the BuyerSight Blog for additional interviews on sales, leadership, and more!

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