#45 Sales operations leadership ft. Hilary Headlee

Pierce Ujjainwalla

By Pierce Ujjainwalla


Published Dec 1, 2022

#45 Sales operations leadership ft. Hilary Headlee

Hilary Headlee didn’t have the most conventional transition into sales operations. After interning at a radio station in college, she was asked to help organize and manage their client database (now known as customer relationship management). From there she realized how much she enjoyed working on the systems side of the job and the environment of the sales floor. After numerous transitions between positions and expanding her roles through different companies, she is now the EVP of Sales and Customer Success at Insight Partners.

Hilary knows that a strong and supported sales team is key to having successful client relationships. Her passion for her sales teams’ success inspired her to work hard and help her team down to the individual level. Adaptability and attentiveness are two keys which she believes strongly have aided not only her but her team’s success. And her past colleagues say the same thing — if you ever read through her LinkedIn, her great leadership skills are something that come up regularly.

Beyond being a great leader, Hilary has also found success in sales. She knows that not one sole background is necessary to thrive in sales, but she can see what is needed through people’s character. In her experience, effective listening and proactiveness with the ability to problem solve are two attributes of a promising sales candidate. Having empathy for sales operators however, she believes is the most necessary skill when hiring a new candidate.

Her love and experience have driven Hilary to be a leading force on the sales operations team. She knows her team and knows how to support them with the proper guidance and technology to back them. Join the conversation between Pierce Ujjainwalla and Hilary Headlee as they dive into all things sales.

You can also follow Hilary Headlee on LinkedIn here.

Thanks for listening to Unsubscribed! – a podcast created by Knak. If you enjoyed this episode, please do subscribe and leave a review on your favourite podcast player. If you have any feedback, or want to chat, feel free to reach out to Pierce on LinkedIn or follow him on Twitter @marketing_101.

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Pierce Ujjainwalla


Pierce Ujjainwalla

Co-Founder & CEO, Knak

Pierce is a career marketer who has lived in the marketing trenches at companies like IBM, SAP, NVIDIA, and Marketo. He launched Knak in 2015 as a platform designed to help Marketers simplify email creation. He is also the founder of Revenue Pulse, a marketing operations consultancy.

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