Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on November 4th, 2021

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Apple to HubSpot, Lessons in leadership from Kelly Brooks

Podcast | HubSpot

Kelly Brooks, Director of Small Business at HubSpot. People leadership is at the core of Kelly's values. She shares her amazing growth journey from Apple and the many wins and losses she had after joining HubSpot.

She shares that the best way to grow into a sales leader position is to be an inch in front of your reps. Kelly also details her reflection process on setting intentions and creating boundaries for the best work and life balance.

Kelly also shares how she bounces back after setbacks both big and small. For her, it is what you do about it today that matters the most. Leaders must also embody that change can be uncomfortable but being united with company visions creates amazing results.

Episode Notes


02:28 Growing in people leadership with Apple and joining HubSpot

09:10 Embodying people leadership and paying it forward

10:52 Mindset shift: From working for someone to serving your people

13:09 Leading versus selling: Proactive versus reactive

16:36 Servant leaders set intention, write them down and have boundaries

19:54 Measure success: Set priorities and know your team's goals

25:49 Leaders teach positive habits through repetition

28:43 Bouncing back from setbacks and having conversations about change

36:40 Be okay that change can be uncomfortable but goals make it worth it

38:37 Leaders with a human touch inspire their organizations

42:24 Connect with Kelly


27:06 "What I see a lot is new leader step in, and they forget that not everyone has those habits. And it's not always a will thing. Often it's a skill thing. with, we need to teach them their role as a leader is to teach those habits... They need to do a lot more repetition."

30:14 "Okay, I had a bummer quarter. I could look at that as like a big, hairy goal. How do I break that down to say, okay, well, what would a better quarter look like moving forward and how does that translate into what I'm going to do today? What is the behavior I'm going to do today to make that outcome?"

34:00 "Oftentimes resistance to change comes from lack of understanding or from sometimes overestimating the amount that is changing. And so I think taking the change and creating clarity in what is changing and, just as importantly, what isn't changing is really important for people."

35:53 "It's so important to figure out how you feel about it, be part of the conversation, be authentic. And also, if things are objectively crummy, like if a change is negatively impacting someone, I think it's okay to acknowledge that." 

41:18 "It's not even a big losses. It can be micro losses, but winning and winning in a sustainable, repeatable, predictable way is a product of reflection and commitment to the process. And I don't think that you get there without some kind of loss or some kind of hardship."

You can learn more about Kelly and ask her about available positions in HubSpot in the links below.


About Jordan Benjamin

Jordan is the founder of My Core OS. After spending years in sales, working with sellers and studying peak performance he found an opportunity to help sellers level up to not only build peak performance at work, but to also create harmony between work and life so you can sustain performance over the long term.