Q&A with Marketing Leaders: Hollie Wegman, VP of Marketing at Segment

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Our series, Q&A with Marketing Leaders, is built to provide SaaS marketing leaders with the best insights and actionable tips on how to improve their marketing planning by learning from the best marketers in the industry.

In this edition, we have a real treat for everyone! We got to meet with Hollie Wegman, VP of Marketing at Segment, one of the fastest growing SaaS companies in the market.

Segment provides customer data infrastructure for thousands of companies, from fast-growing businesses such as Atlassian, Bonobos, and Instacart to some of the world’s largest organizations like Levi’s, Intuit, and Time. With Segment, companies can collect, unify, and connect their first-party data to over 200 marketing, analytics, and data warehousing tools to achieve a common understanding of their customers.

Hollie is Vice President of Marketing at Segment. Known for her strong team-building and her versatility of expertise, she has successfully led every aspect of marketing including product marketing, brand and growth. Her company experience ranges broadly having successfully marketed in both Fortune 500 organizations (Salesforce, Cisco) and growing tech brands (MuleSoft, Envoy).

What was the best marketing advice that you’ve gotten in your career?

Early in my career, when I was in consumer marketing, I got the advice to always come with a point-of-view…meaning come to the table with an opinion on what’s happening around you and share that opinion. It was great advice for me especially so early in my career because it taught me that no one has all the answers, it’s up to us all to wade through the data and the different views and decide what to do. It also taught me that my opinion is the valuable part I bring to the business.

What is the most common marketing mistake you see?

The mistake I see a lot is “fortune cookie” marketing. When building messaging, you wind up trying to appeal to so many people that you appeal to everyone. It’s like a fortune cookie, usually when you open one you can think of a way the fortune applies to you, but at the same time, it doesn’t really tell you anything. My favorite example of this was a website I visited where the headline was “Taking you from where you are, to where you want to go”. That could basically apply to anything from a pair of shoes to an escalator. It’s important to keep the message tight even if it means you don’t speak to every possible audience.

It’s going to become increasingly important to have a direct relationship with your customers and to really know them and their communication choices and preferences.

How is marketing going to change in the next 5 years in your opinion?

The biggest change I see coming for marketing is our relationship with customer data.

Consumers and customers today are increasingly sensitive to “creepy” marketing. In my mind, it’s going to become increasingly important to have a direct relationship with your customers and to really know them and their communication choices and preferences. I don’t think they want you to have information about them that they don’t know how you got.

What is the most important skill that marketing leaders need to have in your opinion?


The most important skill for me is learning. It may not sound like a skill, but I think that no one skill will always apply. The best leaders I’ve worked with constantly learn and evolve and I feel like I can never learn enough about marketing. Every day I learn from blogs, influencers, videos, vendors and my own team. Marketing is a deep and varied subject and fascinating in its mix of art and science/tech. The learning opportunities are great.

Who was the biggest marketing influencer/inspiration in your career?

I find that I learn as much from my teams as I do from other marketing or company leaders. One person I’ve always admired very much is Melissa Czapiga (Corporate Marketing at MuleSoft). Before I met Melissa, I always thought of PR as the “fluffy” part of marketing and this was such a huge misconception. Melissa taught me so many things about PR when she was on my team at MuleSoft. She especially taught me that PR is the most strategic part of marketing in that it is where the market narrative resides. She also has the highest level of polish and professionalism of anyone I’ve ever worked with. No matter how hot the issue or how tight the timeline, she always took her time and was thoughtful.

What is your biggest challenge in terms of marketing strategy/planning?

The biggest challenge I have right now is that I work in a company where we are basically operating at a new scale every 90 days. Segment is growing so fast that the needs change constantly and I have to think not on a scale of years, but on a scale of quarters. This means marketing strategy is not a “set it and forget it” kind of endeavor. It’s constantly flexing and moving with the new demands of a growing business. It’s exhilarating, but it’s also tough!

Marketing strategy is not a “set it and forget it” kind of endeavor. It’s constantly flexing and moving with the new demands of a growing business.

What are two things you’ve done well in terms of marketing strategy?

I think, perhaps, differently about marketing strategy than most. I definitely over-rotate on the people driving the strategy versus the strategy itself. I believe the right people will generate the right strategy almost organically. So, there are two things I feel most proud of that are related to that. The first is designing a highly cross-functional marketing organization that works collaboratively with engineering, product, design, analytics, sales and customer success (and finance and HR…). Many leaders discount this when planning their marketing strategy. No marketing team can function in a vacuum because marketing teams don’t succeed, companies succeed. The other thing I feel good about is the team at Segment. We have tripled the marketing team at Segment in less than a year and I feel proud every day to say I am part of that team.

What is your best advice for a young CMO in terms of marketing strategy/planning?

I was a management consultant for the first many years of my career and I think that was really good for me because I learned to think of the business first and the functions that run the business second. The advice I’d give is to always keep clear what the business is trying to achieve first. Marketing should both drive the business as well as tailor to it.

What marketing channel you think is the most underrated on today marketing scene?

Okay don’t think I am crazy, but I think direct mail is baaaaack! I think a well-targeted, personalized direct mail campaign with something delightful and surprising is a way to capture the attention of a buyer or consumer who might otherwise shut you out. Even though most of us dread snail mail, we still have this little part of us that is optimistic and excited when we open the mail. Marketers can capitalize on this if they do it cleverly and thoughtfully.

What are your best practices for marketing planning/strategy?

At Segment, we like to consider carefully the overall business goals and we then try to understand where we might have cross-functional dependencies (e.g., sales needs marketing and marketing needs sales). The key best practice here is to not create a marketing plan in isolation. The first phase of marketing planning is to understand the needs of the business and understand our own cross-functional needs and to meet with other teams to make sure we take these things into our planning cycle. I also think that it’s important, in the planning cycle, to consider the marketing team members and to think carefully about the interests and career aspirations of the people on the team so we can give growth opportunities to the current people and hire for places where we might have gaps or need to scale.

I try to think of our marketing plan as 80% done versus 100%. We try to leave 20% of our time/resources open to the flexibilities of the business and opportunities of the market.

How do you know that you planned well?

We are getting into the practice now of doing quarterly retrospectives. We can tell we have planned well when we hit around 80% of our goals. If we hit 100% it probably means we didn’t set high enough goals. We also judge, each quarter, employee sentiment through a company-wide survey. If we hit our goals and we have poor sentiment that, to me, is akin to failure. So the signals of planning well are coming close to but not crushing the goals and also having good team sentiment.

How often you adjust your marketing plan after you create it?

We adjust often, but our goal is to have a certain core of predictability. I try to think of our marketing plan as 80% done versus 100%. We try to leave 20% of our time/resources open to the flexibilities of the business and opportunities of the market. We adjust within that last 20% on a rolling basis. The core 80% we should only adjust if we can swap one priority for another.