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A conversation with Jeanne Hopkins of Lola.com

As a part of our series about “Marketing Strategies From The Top” I had the pleasure of interviewing Jeanne Hopkins. Jeanne is Chief Marketing Officer at Lola.com, leading the company’s marketing organization as well as customer success. She was Executive Vice President and CMO at Ipswitch and held executive marketing roles at HubSpot, Symmetricom (now Microsemi), […]

As a part of our series about “Marketing Strategies From The Top” I had the pleasure of interviewing Jeanne Hopkins. Jeanne is Chief Marketing Officer at Lola.com, leading the company’s marketing organization as well as customer success. She was Executive Vice President and CMO at Ipswitch and held executive marketing roles at HubSpot, Symmetricom (now Microsemi), SmartBear, MarketingSherpa, and Continuum (now ConnectWise). At HubSpot, Jeanne’s leadership helped the company land on the number two spot on the Inc. 500 list of fastest growing companies by generating 50,000 net new leads per month. An accomplished writer, advisor and speaker, Jeanne serves on the Advisory Boards of Coffee Cup Collective and Sales Lead Management Association, and Co-Chair of the MassTLC Sales and Marketing Group.


Thank you so much for doing this with us! Before we dig in, or readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Marketing is something I love doing — selling, communicating, planning, executing, growing — everything fits in a Marketing function. I enjoy the building of a program and teaching others how to do it. It’s a little bit of art, a lot of science, and a bunch of smiles. It’s all good.

Can you share a story about the funniest marketing mistake you made when you were first starting? Can you tell us what lesson you learned from that?

That a “test” list should be double-checked! I created a survey for our 50K+ customers to get feedback about the product, and meant to send it to a TEST list for review when, in fact, I sent to all 50K+ with the message, “Hey, could you give me some feedback on the questions to make sure they makes sense?” And, when I saw the send going and going and going and absolutely no way to stop it, my face was brilliantly red. Like most mistakes, there was a good outcome, because I asked for help, I had a wicked high response rate, and was also able to improve the survey questions. All in all, a good lesson.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

I think being able to add value to other functions rather than fighting others off with a stick is a good point in anyone’s career. Not everyone is going to like you. And, you have little ability to MAKE someone like you. All you can change is your response to them. I find a little TLC goes a long way. They are the ones that look foolish in the face of your niceness. “Smile and wave” is my motto for horn-tooting Boston drivers, and people who aren’t awesome.

What do you think makes your company stand out? Can you share a story?

We have so many stories from our Wombats, our 24/7 service team that helps business travelers every day get to where they need to be as easy as possible. With satisfaction scores at 98%+, it is wonderful for our customers to have this service. Add the highest-rated travel management platform score of 4.8/5 from our installed base, and we have a win/win for Lola.com and our customers.

Are you working on any exciting new projects now? How do you think that will help people?

There are lots of exciting projects with partnerships like American Express Global Business Travel, Expensify, Zoho, Priceline. Companies want to work with a red hot startup like Lola.com.

What advice would you give to other marketers to thrive and avoid burnout?

Delegate. Seriously, you cannot do everything. Find ways to help your team grow by giving them significant projects to learn. Without your confidence in their efforts, they will not thrive, and you will definitely burn out.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve been very lucky to work for some amazing people, and some not so amazing people. I feel I’ve learned a lot from both types — what to do and what not to do. I am grateful for my team, and the people I get to work with each and every day. Lola.com is truly #wickedloving, and I have been given the opportunity to grow something that has value. Doesn’t get much better than that.

Ok super. Let’s now shift to the main part of our discussion. There are hundreds of memorable marketing campaigns that have become part of the lexicon of our culture. What is your favorite marketing or branding campaign from history? Can you explain why you like that so much?

Okay, you are going to laugh at me. I am a big Harry Potter fan. And, I was lucky to see an exhibit of JK Rowling’s thoughts, notes, drawings etc. that led to her creation of seven distinct, yet cohesive books. What amazed me is the care and feeding she put into the naming of her characters, the planning document (a hand-drawn spreadsheet) and the imagery she envisioned. Ultimately, this was a marketing campaign for something that may not have gone anywhere, yet she planned it and knew where she wanted to go. That sticks with me, not because it was a one-off, and I learned more from the planning and the various inputs from life that can lead to a truly awesome outcome.

If you could break down a very successful campaign into a “blueprint”, what would that blueprint look like? Please share some stories or examples of your ideas.

Give yourself enough time, and treat everything you do like a product launch. Tier your launches into 1, 2, 3 and everything, every feature, every campaign, every email have to be one of those things. Launch internally, launch to your customers, and then launch to prospects. Look for ways to find the “gotchas” in your launch beforehand. A communication brief that includes the overall messaging, the goals, the participants, and a debrief of the outcome is essential. We should all have a file of what did NOT work. And, share that with the company. Not everything is great, and we learn from our #fails as well.

Companies like Google and Facebook have totally disrupted how companies market over the past 15 years. At the same time, consumers have become more jaded and resistant to anything “salesy”. In your industry, where do you see the future of marketing going?

Making customers feel like more than a paycheck. We are all customers, and we all become irked by the lack of attention paid to us. Why should a new user get a promo but an ongoing customer does not? Just once, I would love it if Amazon said, “Hey, thanks for being a Prime customer for 19 years!” (That is a true statement; I bought Prime when it first came out.) Yet, Amazon charges more, and I’m looking at alternatives. I believe we need to thank our customers more, and that is why I use Thnks for my entire company to send little “thanks a latte” gifts that are very well-received and noted.

Can you please tell us the 5 things you wish someone told you before you started? Can you please share a story or example for each.

  1. I read fast and my boss @LEGO told me that I read “too fast” and comprehend info “too quickly” before others can catch up. Lesson? Let others speak first.
  2. Being part of a team, I like getting stuff done, and sometimes others need more time to learn and process. Lesson? My way is not the only way.
  3. Don’t disparage others. Just because you don’t like someone, doesn’t mean they don’t have value. Lesson? Always say nice things or nothing at all (including eye-rolls).
  4. Get your stuff in on time or early. The Finance team is always struggling to make the month, the quarter, the year-end on time. And, if you delay, that hurts them. Lesson? We are all trying hard.
  5. Ask questions. If you don’t know something, ask. Lesson? We do not know everything.

Can you share a few examples of marketing tools or marketing technology that you think can dramatically empower small business owners to become more effective marketers?

A CRM (customer relationship management) for starters, a platform that allows you to figure out who your customers are and how you are touching them. A CMS allows you to create content for your customers and prospects. Creating content, and seeing what works is critical. Small businesses forget to Get Found by making sure they are on Google Maps, where their customers might be searching.

What books, podcasts, documentaries or other resources do you use to sharpen your marketing skills?

I am a voracious reader, the NY Times and the Boston Globe daily, The New Yorker (for the cartoons) weekly; and I subscribe to Blinkist, which gives me a chance to get a quick overview of relevant books that I can get into later if the need warrants. MarketingProfs, MarketingSherpa, and B2B Demand Gen are all digital publications that I can learn from every day and are a resource. Reading my LinkedIn feed to connect with interesting people and looking at Twitter — as well as sharing content are critical.

Who is your hero? Can you explain or share a story about why that person resonates with you?

For me, it starts with my maternal grandmother. She took the train for two hours from Andover, MA to Boston daily to attend Simmons College. She graduated valedictorian of her class in 1925! With a major in French (go figure!). When she married my grandfather, it was in the depths of the Depression, and she was the Assistant to the President of Wheaton College supporting the family. Dorothy was my biggest fan, and I miss her daily.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

You never know what your idea can trigger. 🙂 I wish more people would use LinkedIn to write recommendations for their peers, their team, their vendors, their partners. If you could just write one recommendation for someone who has not requested one from you, that would be awesome. I’m trying to get this going at Lola.com for International Women’s Day on March 8 by having everyone write just one for someone they know. Paying things forward is the best possible thing anyone can do easily. #wickedloving

How can our readers follow you online?

Please follow me at:

Twitter: @jeannehopkins

LinkedIn: https://www.linkedin.com/in/jeannehopkins/

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