• Sofia Sulikowski

I Talked to 32 Marketers at HubSpot. Here's What I Learned.

Updated: Oct 19, 2020

Aka: leveling up my conversation skills

This January, I started learning about marketing careers. To prepare for the upcoming school-to-career transition, I set a summer project for myself: talk to one person from each marketing team at HubSpot. The 32 resulting conversations taught, inspired, and excited me more than anything else this year.

Reasons: Why?

1. Understand what marketing roles in tech mean and involve

Each industry has slightly different roles and when a close family friend indicated tech might be a good fit for me, I had no idea marketing roles even existed in the category. Titles like Product Marketing Manager and Customer Marketer were new to me, and familiar ones, like Brand Marketing, look very different depending on the company and field.

2. Figure out what marketing specialties align best with my interests and skills

Without knowing my options, I couldn't know where I'd fit best and what marketing specialties piqued my interest. HubSpot has a very robust, talented marketing team with almost every type of role represented, so it offered a fairly complete sample to draw from.

3. Meet marketing professionals

I love meeting new people and marketers tend to be cool :)

Now that conversations with new people are pretty rare, I wanted to incorporate the element back into my weeks.

4. Learn about a company I admire

If you read my other posts here, it's no secret: I admire HubSpot's product, culture, and business. I spoke with a few Georgetown alums across the company when I first learned about HubSpot, which left me wanting to learn more. And there's no better way to understand a company's inner workings than by talking to its community members.

5. Prepare for recruiting

I knew I wanted to apply to their entry-level program this fall, so I set out to learn about the different teams to see where I might fit best specifically at HubSpot.

Best Practices

I've written about informational interviews before, but this project dives deeper into how to best approach conversations with multiple teams from the same company. The best practices I developed and modified along the way can be applied to engaging with any organization.

Introduce yourself

This seems silly to include. But I wasn't introducing myself properly at first. I figured out about halfway through that a clear, comprehensive introduction sets the stage for the rest of the conversation. Good intro = more valuable and smoother conversation. Thank you to Josh, who mentioned over-introducing the context is always better—even if you outlined an intro via email, most people appreciate the reminder.

  • Basic details: school, year, major/interests, location

  • Context: your goal for the conversation, how much you already know, how the person on the other end of the phone fits into the picture (ie. how they can help you).

Ask them to introduce themselves

The flip side. I used to jump right into specific questions but ran into multiple situations where I assumed areas of expertise or backgrounds incorrectly from the person's LinkedIn profile. Prompting "tell me a bit about yourself and your role" helped with last-minute question tweaks. Also, people tend to self-identify interests and areas of importance in their intros, which can help guide the conversation in the right directions.


Unless the person you're talking to excels at going through their role in a single, 30-minute response (a 1/32 rate of occurrence in my case), conversations will only be as good as the questions you ask. Although true for all conversations, it's especially important for calls in which you already know the basics. This became clear to me around conversation #15. Until then, I was asking everyone the following questions:

  1. What are some initiatives you are working on now?

  2. What are the success metrics on your team used to evaluate the outcome of those initiatives?

  3. Which other teams do you work with most closely? What are their roles in your initiatives?

  4. What are three skills/areas of expertise you need to succeed in your field?

  5. What advice would you offer someone soon to graduate college?

I received great information, but eventually, the answers started to overlap across conversations. And in the event two people from the same team offered me their time, I didn't know how to expand upon the first team-specific conversation.

So I added the following key question(s):

What other questions should I be asking? What is your favorite question to ask marketers to learn about them and their roles?

Which led me to incorporate the following questions (depending on their fit with each conversation):

  1. How do you make the business money?

  2. How does HubSpot's culture affect your role and experience?

  3. What side projects are you working on?

  4. What mistake or challenge have you learned the most from?

  5. What’s next in your career?

Practice indeed makes perfect— my ability to align meaningful questions to each person's experiences and smooth out transitions between topics dramatically improved from conversation one (a somewhat awkward and choppy encounter).

How to find people for more conversations

Getting hold of one person at a company seems hard enough but 30+...? Surprisingly, the more people you talk to, the easier it gets to build the momentum. I found people by:

  1. Sending a customized LinkedIn message describing my project and how they could help

  2. Directly asking a) "who do you admire most from a neighboring team and why" or b) "I'm looking to talk to someone from XYZ team, does anyone come to mind who you recommend reaching out to?"

The ask can be intimidating, but most people want to help after confirming you're genuinely interested in learning.


  • Talking to people is the way to go for industry-specific knowledge. Marketing evolved from a conventional role to one of rapid change, and university classes don't yet reflect the transition.

  • I know nothing. But I'm learning faster than ever. Not only were the conversations informative, but they were also inspiring. The expertise and communication skills in action I heard through the phone painted a clear picture of how far I have to go to transition from awkward-and-nervous to collected-and-confident. I'm still a total beginner, but I'm 5x further along than when I started in 2020.

  • My marketing interests. In the last four months, I went from being undecided in the face of upcoming career decisions (a very uncomfortable feeling) to figuring out my marketing interests: product marketing, conversational marketing, and solutions marketing (among a few other cool ones, of course. Can't be too decided yet ;p). I don't think I would have asked as many questions about every role had I not been undecided. In this case, my blank slate served as a strength. I didn't know what I wanted to do, but I knew I could talk to a diverse group of marketers and figure it out along the way. Since my initial "ooh that sounds extra cool" reaction to certain roles, I've found ways to learn more with Sharebird, Product Marketing Alliance, and Conversations Conference 2020. The scoping continues.

Career-changing advice

Since I received much good advice over the last few months, it's only fair I pass along the gold.

None of the following thoughts are mine:

  • Ask questions. Everywhere and all the time. (Also: "Be a sponge")

  • Leadership matters. Choose a manager, not a role. Choose a company, not a title.

  • Get really good at writing and speaking. Communicating effectively is a superpower.

  • Luck favors those who are prepared and ready for the next opportunity

  • The best way to learn is to do a lot of free stuff

  • Write or create publicly to build your career

  • Invest in relationship building. You can't know everything but you can know the right people.

  • Learn by surrounding yourself with experts on what you want to do

  • Spend as much time creating as you do consuming

I'm planning to replicate the project for different companies (to a slightly smaller extent) because I truly cannot put into words the value of all the conversations combined. People want to help you learn—don't let the very-valid-but-unhelpful fear of the unknown stop you from reaching out.

Thank you to everyone who shared their time and expertise to make my learning possible!

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