June 30th marked the end of my participation in HubSpot’s Leadership Rotational Program—a two year intense program designed to train new college grads to become marketing managers. Here are 11 lessons that I’ve learned in the 2 year program. 

Life Before HubSpot

Let’s wind the clocks back three years. I was a senior in college thinking about how I’d begin my career. After coming to HubSpot for my interviews and meeting HubSpotters, I was thrilled to be considered for HubSpot’s Leadership Rotational Program (LRP) which provides new grads the opportunity to rotate in three different teams within two years. The decision to move to Boston wasn’t easy. I lived in California my whole life and didn’t know anyone in Boston. It would be a “starting over” journey. But the opportunity seemed 100% worth it. Luckily, I was chosen as one of the three LRPs for 2018 along with Sammi and Lucy. They were the best part about LRP for me since they became my close friends after moving to Boston. 

HubSpot Leadership Rotational Program members in group picture

Now that I’ve completed the program, I can say that it was the right decision. I’ve learned so much in the past two years working with some of the smartest people and completing on interesting projects. Below, I breakdown my three rotations and distill the lessons that I’m taking with me as I start on the Product Marketing team in July.

First Rotation: Customer Support (July 2018 – Feb 2019)

I’m not going to lie, I was worried about my first rotation in customer support. Not only was I shy when it came to talking to strangers over the phone, but I also didn’t know how I—with little product knowledge—could be helpful to HubSpot customers. Thankfully, customer support is equipped with talented coaches and mentors who train you to be better at delivering great customer experiences. It was eye-opening to see that I could make a direct impact on the businesses that operate using HubSpot.

Lesson 1: Understand the problem—Ask questions until you’re 100% sure you’re solving the right problem. 

In customer support, you constantly see unfamiliar technical issues. “What’s an API? You’ve reached a limit?” “Your Outlook is disconnected from HubSpot?” As a HubSpot newbie, a customer’s guess at solving the issue was as good as mine. But my manager and the Support Team Leads helped me understand how to troubleshoot issues on my own. The trick in support is to diagnose the correct issue as fast as possible. For example, a customer may suggest that the problem is in their HubSpot properties not syncing correctly. But it may actually be that they forgot to tag the correct personalization token in their marketing emails. The key here is to ask questions to pinpoint why the customer has an issue. Helpful questions include: “Can you tell me how you experienced the problem?” Or “What steps did you take for this to happen.”

Three months into my rotation, I learned the most important question to ask if I was really confused. The question is: “What’s your end goal?” This question gets the customer to talk about what they want to achieve. Without it, you can go down a rabbit hole of fixes that don’t actually help the customer achieve what they want.

Lesson 2: Troubleshooting is a skill. Once you’ve diagnosed the problem, try solving it using the resources at your disposal.

I wasn’t going to know everything about HubSpot’s products. I had to accept that my lack of product knowledge shouldn’t affect the way I navigate conversations with customers. I ran into cases that I couldn’t figure out over the phone. I had to let the customer know that I’d follow up with them with a solution. The Support Team Leads deliberately avoided giving us answers to customer cases. Instead, they asked us questions that make us think of ways to probe for a solution. Before asking for help, you want to get as far as you can with the resources you have. This builds resiliency to go through the documentation, slack messages, past cases, and JIRAs to find a solution for the customer.

Lesson 3: Be careful about making assumptions

I always thought that only angry people called into customer support. We had to make our first call during our ramp period (the first couple months that you get comfortable in your role). Matthew, my coach, looked over my shoulder and noted how I was performing on the phone with the customer. I assumed that the customer was angry. Oddly enough, the customer was actually a cool person who needed help in understanding his marketing emails. He wasn’t demanding. He wasn’t frustrated with me. Although I couldn’t solve his problem over the phone, I followed up with the correct solution. The best part—he gave me a 10/10 NPS score (a “job-well-done rating). While I thought I had delivered a terrible experience, the customer thought that I was doing the right thing since he considered me a HubSpot expert. Assumptions are crucial. Don’t make assumptions about what others may think about you. For example, I shouldn’t have assumed that the customer knew that he was my first case.

Lesson 4: How to prioritize decisions

One of my favorite parts about the Leadership Rotational Program was the opportunity to have lunches with HubSpot executives, like Brian Halligan (CEO), Dharmesh Shah (CTO), and Allison Elworthy (VP of Customer Service). We asked them questions about HubSpot’s business and their own careers. One constant theme that I found was the executives’ commitment to making only a few important decisions. Most of the executives drew the same 2×2 decision chart that showed how they allocate their time to the most important decisions for the business. These are typically decisions that are impactful and can’t easily be undone. For all other decisions, they lean on their team. So this got me to focus on impactful decisions that were in my control. I usually prioritize decisions based on impact, time, and outcome (those decisions that are most impactful, current, and allow teammates to move forward).

While in Customer Support, I worked 3 marketing projects

1) AcquisitionHubSpot Academy: Ideated HubSpot Academy’s first YouTube Mini-series, called “Pushing Boundaries.”

2) Product Marketing: I met with 14 HubSpotters in the Sales organization to understand how HubSpot can improve the resources provided to Sales Reps who sell Enterprise products.

3) Email Messaging: Organized internal Sales Rep notifications based on prospect triggers (like filling out forms or taking specific actions on hubspot.com).

Living in Dublin for One Month

  • Our trip to Dublin was an incredible opportunity to meet HubSpotters overseas, learn about their stories, and experience a completely different work-life.
  • The common theme was that everyone in Dublin was solving for the customer. Though the customers may be different, DubSpotters solved for their unique customers in their regions.
  • The trio (Lucy, Sammi, and I)  identified and ranked media outlets in the EMEA region like Benelux and the Nordics. Just like the US, every region has its star media outlets and niche websites that prospects turn to. We only scratched the surface in consolidating a list of marketing publications in the EMEA region.
  • While in Dublin, we made trips around the area, from hiking in Howth and the Cliffs of Moher, to checking out the Guinness Factory and Kilmainham gaol. Dublin had a friendly, artsy vibe that I enjoyed. My favorite pub was “The Quays” in Temple Bar. It featured an excellent duo playing classics like “Castle on a Hill” and “I Will Wait”.
Leadership Rotational Program members in Dublin Ireland

Temple Bar, Dublin, Ireland. This whole street is filled with pubs!

Nate Medina with friends in a coffee shop
Emily joined us in Howth, Ireland. I highly recommend hiking in Howth!
Nate Medina and Carl in Howth
Carl joined us in Howth, Ireland as well!

Second Rotation: Product Marketing (March 2019 – November 2019)

While in Support, I reached out to people from the Product Marketing (PMM) team to learn more about their role at HubSpot. They gave me a few book recommendations and highlighted the cool projects that their team was working on. Luckily, there was an opportunity to join the PMM team for my first marketing rotation in March 2019. While on the PMM team, I worked on three main projects.

HubSpot's Product Marketing Team

HubSpot’s Product Marketing team at an annual planning event (a fantastic crew of people!)

1) Upgrade more customers

My first project on the team was to increase the number of customers who upgrade from Marketing Hub Starter (up-sell). This meant knowing how customers typically upgrade, then running a campaign to get more customers to upgrade to a higher priced product. I worked with Product, UX, and Marketing Research teams to understand the Marketing Hub Starter persona—which describes the type of person using Marketing Hub Starter. I conducted an upgrade and usage analysis to inform teams about upgrade path opportunities. I learned that Marketing Hub Starter customers who use HubSpot’s email marketing tool are likely to upgrade their account for workflow automation functionality. Oddly enough, 60% of Starter customers didn’t use the email marketing tool in Q1 2019. Although activating Starter customers doesn’t directly upgrade them, our usage data showed that customers activated on the email tool are more likely to upgrade than any other tool. So it provided us with a good place to start.

We executed an email activation campaign targeting Starter customers with low email marketing tool usage. I used upgrade lessons from the book “Hooked” to create a loop for customers: Learn > activate on tool > get a reward email > see results. With one email, we activated 15% of contacts who interacted with our email campaign.

2) Launch HubSpot Services Update

I led the global re-launch of HubSpot Services website updates across six regions. This was my first positioning project. It was a cross-functional collaboration with Services, Marketing, and Growth to communicate pricing changes, new positioning/messaging, and update website designs externally and internally. Within 90-days, we saw a 97% increase in page views and 349% increase in submissions without a promotional campaign.

Lesson 5: Understand customers’ perceptions

How do you start a positioning project? For me, it helped to interview customers to know what they thought about HubSpot and the services that we provide. Using the stories that customers shared, I felt more confident in communicating HubSpot’s differentiated viewpoint for our new offerings. Going forward, I’ll be sure to get first-hand and unbiased customer feedback to inform product positioning viewpoints from customers.

Check out this blog post that I wrote: Why HubSpot is Changing the Onboarding Experience for Customers

3) Getting our company excited about the Free Email Marketing Launch

I supported the team in launching HubSpot’s free email tool (similar to Mailchimp). I led the internal enablement campaign to educate HubSpotters about the launch. We exceeded our social sharing goal by 300% within one week, and had over 900 HubSpotters participate by sharing or influencing over 3,500 total social media posts.

A sample collage of social posts from HubSpotters

A sample collage of social posts from HubSpotters.

Lesson 6: Learn from past examples, but be fierce in challenging the status quo

I like to stick to what works. If a playbook worked before, why not replicate it for a new project? But, just because something worked before doesn’t mean it can be better. There are opportunities to make improvements to established playbooks. To give an example, for past employee-run campaigns, we typically reward employees based on the highest number of actions that they take (like sharing a tweet). But, we received feedback that this method discourages other HubSpotters from participating simply because they feel like they can’t compete. So, I changed the winner selection process to random selection, which motivated more HubSpotters to participate since everyone felt like they had a shot at winning.

What I loved about Product Marketing is that the work is tied closely to our customer and sales teams (bottom of the funnel). I enjoy researching our competitors and writing customer case studies and competitive pages. It’s rewarding to help Sales Reps close deals or help marketing teams up-sell more customers.

Lesson 7: Optimize for impact

How do you make decisions that are most impactful to our customers or to the business? A mentor gave me good advice here that’s helped me reflect on how I should prioritize my time. She told me to work backwards. Figure out what you need to accomplish and why, and think about the most essential pieces that need to be completed to help you get there.

Third Rotation: Acquisition Marketing, Global Campaigns (December 2019 – June 2020)

While in Product Marketing, I saw the amazing work done by our Acquisition Campaigns team in building global campaigns like Make My PersonaEmail Signature Generator, and Behind the Screens. I wanted to learn how this team produced marketing campaigns at a global scale. Fortunately, there was an opportunity to join the Campaigns team for my last marketing rotation.

Website Grader Global Re-launch

I was challenged to develop the campaign for the second quarter of 2020. What messaging would HubSpot put into the market to attract and engage new visitors? I started out by researching our target audience for the editorial push in Q2. After brainstorming with other teams, it became clear that a Website Grader rebuild would be a fantastic opportunity to coincide with HubSpot’s CMS Hub launch (website content management system). The only problem—our team didn’t have permission to rebuild Website Grader as the tool was owned by the SEO Product team. I wrote about how convinced the SEO Product team to rebuild Website Grader for our campaign. 




Lesson 8: Relationships are everything

This involves knowing other team members and their goals. Early on,  my manager (@denhoff_) taught me a valuable piece of advice. He said to always ask your counterpart what their goals are so that you’re aware of how you can help your counterpart hit their goals, too. This meant that we’d work with different teams on our campaigns while also looking for ways to support their goals. I had already built a relationship with the SEO Product Manager who was the decision-maker on Website Grader’s future. This relationship helped our team explore the possibility of utilizing Website Grader for our campaign. It also helped having a creative team equipped with the tools and skills to make the campaign happen. The creative team was absolutely phenomenal to work with. 

Lesson 9: Use data to get buy-in

After researching the opportunity to turn Website Grader into an acquisition tool, it became clear that we could deliver more value to the business and to our users. We installed Hotjar on Website Grader to learn how users would improve the tool. We found that 12% of user comments suggested additional guidance in translating insights into tactical fixes for their websites. On top of that, there were opportunities to increase Website Grader’s organic traffic and improve its design. Using the research and data points, I pitched our ideas to the SEO Product Manager. After that meeting, we formed a partnership to rebuild Website Grader into our Q2 campaign.

Lesson 10: Look for insights

When working on a cross-functional and multi-objective campaign, it helps to be diligent in selecting the insights from research. For example, we learned that 12% of Website Grader users wanted additional education to fix their websites. We also knew that the HubSpot Academy (free video education) users were a safer bet against tightening data-privacy regulations rather than leads from a standard 8-field form. We knew there could be an opportunity to partner with the Academy team to fill in the education gap for our users. We worked alongside the HubSpot Academy team and our creative video partners to define the course content and production. Being aware of these insights helped us clarify the campaign’s objectives. We’ve received good feedback on the course that we build for Website Grader because we followed the insights from our research. One user said, “As a result of doing this course and being able to clearly discuss the changes I wanted made with my developer, website grade went from 84 to 97.”

Lesson 11: Use sprint planning to make big decisions

We led a sprint plan to develop a creative concept and get leadership buy-in. Sprint allowed us to nail our campaign’s creative concept in five days by bringing together the right stakeholders to inform our work and define mechanisms to get leadership decisions. We landed on a concept titled, “The Score is Not Enough,” that we used for the campaign’s thought track.

Check out the blog post: “How Our Marketing Team Used Sprint Planning While Working Remotely

Co-Marketing Campaigns

While working on the Website Grader global campaign, I supported the launch of co-marketing campaigns. Before joining the team, I was impressed with how we negotiated with partners from other companies to collaborate with them on lead-gen campaigns. While on the team, I  created 2 offers, wrote a blog post for LinkedIn, and shared leads with our partners weekly.

What’s Next

After my last rotation, I’m excited to join the Product Marketing team to support product launches! I look forward to using what I’ve learned in the Leadership Rotational Program in my new role. Thank you HubSpot’s Marketing leadership and other folks involved in running this amazing Leadership Rotational Program.

I want to give a big thanks to my mentors for providing remarkable advice as my mentor in the program. Thanks for helping me navigate my career at HubSpot.

If you’re a college senior, apply to HubSpot’s Leadership Program

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