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  • Writer's pictureZach Servideo

083: Boston Speaks Up with Scott Ernst, Drift CEO

Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs. Listen to BSU on any podcast platform you choose: SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play.

Scott Ernst is an entrepreneur who’s been at the intersection of market research, commerce and technology for three decades. He was building startups on Newbury Street in Boston long before this recent wave of VCs and startups began moving into the Back Bay area.

After stints at multiple startups in the 1990s, Ernst was a founding management team member of Compete in the 2000s and helped the company grow to a $100 million revenue business resulting in the 2008 acquisition by MIllward Brown Digital/WPP’s Kantar.

In June 2022, he made headlines for his appointment as CEO of Boston-based Drift, a marketing technology trailblazer best known for single-handedly introducing conversational marketing to the market. Ernst joined his friend, company co-founder and long-time CEO, David Cancel, who stepped into the role of Executive Chairman.

Ernst most recently served as CEO of Tubular Labs, a social video analytics company headquartered in San Francisco. Prior to that, he was the CEO of Macromill, a Tokyo-based global marketing research business, which he took through an IPO with an enterprise value of over $1 billion.

In this episode, Ernst discusses the future of Drift, OG Boston tech, his time in Japan, taking a company from early stage to IPO, how San Francisco and Boston compare, the future of marketing and much more.

You can listen to our podcast discussion embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):

Pre-Podcast Q&A

Where did you grow up? And how would you describe your childhood?

  • Grew up in a small town, Tiverton RI, outside of Newport

  • Classic small-town USA, with a beach, liquor store and a couple restaurants but very much a boating vibe. Our family time was centered around sailing in the summer, skiing in North Conway in the winter and youth sports (mostly football) in between

  • Sometimes you need to get away to appreciate how amazing it as where you grew up in such a special place

What is one of the biggest lessons you learned from your parents?

My parents were both first generation in the US and my Dad was the epitome of a self-made man:

  • Grew up in Pittsburg, PA

  • Joined the Navy to get away

  • Started his own company in his 30’s. I remember him describing the risks of being an entrepreneur (although I don’t think we referred to it as entrepreneurship back then)

  • Meaningful impact on our family and many of families that were involved with him

  • He is now 82, and still runs his own business and works every day

Lesson – you can achieve anything if you have passion and are committed - can create life changing experiences for your family and your team

What is the first career you remember wanting to pursue?

  • From very early on I decided I wanted to go to an Ivy League school, be a doctor and play college football. Well, two-out-of-three, not bad

  • At Penn, realized that I was kind of squeamish about blood, transferred to Wharton, and the rest as they say is history

  • That brought me to the Bay Area for my first start up in health care

  • Then first internet happened, early ‘digital guy’ and now 30 years at the intersection of marketing, tech and customer data

Is there a particular person or event that helped shape the career path you took?

Don McLagan, my early CEO at Compete:

  • Legend in Boston data scene, Data Resources (DRI), Lotus, NewsEdge

  • Worked closely together, me running Sales and BD, that’s where I met David Cancel

  • All built Compete together along with folks Stephen DiMarco, TJ Mahony, Ryan Burke and a whole cast of amazing people, many of which are still prominent in the Boston tech scene. Great to see

  • Don believed in the power of strong and committed teams, saw something in me, gave me broader responsibilities and I became his successor at Compete and then ran Compete inside WPP (the world’s largest marketing service company)

What is the biggest challenge you’ve overcome getting to where you are today?

  • Transition from sales to executive leadership

  • Figuring out how to turn off (or at least mute the imposter syndrome voices)

As a CEO, do you have any advice for young people that would like to grow to that level in their respective organizations?

  • Find your passion

  • Invest in yourself (don’t outsource your career development to your manager)

  • Get comfortable with being uncomfortable

How would you sum up the Boston startup scene in the 2000s?

  • Coming off the first crash (I lived it in the bay area during first wave)

  • Back to more sane / rational company growth

  • A bit more ‘Yankee sensibilities’

  • Chip on our shoulder, trying to compete against Bay Area

In your view, what’s the biggest similarity and what’s the biggest difference between Boston and San Francisco?


  • Active ecosystem for early-stage companies

  • Great hubs for talent

  • Digital first creating new opportunities and challenges with building teams and scaling companies


  • More activity, deal flow, start-up mind set in Bay Area

  • More bigger exits, more competitive environment, faster pace

  • Race for talent everywhere, more frantic in valley

What was it like leading a company in Tokyo? And what did you take away from your time living in Japan?

  • Amazing, life changing experience

  • More rewarding and challenging experience

  • Strategy is important, culture is hard

  • Perspective of growing global companies for US and from Global into US

As we head toward 2023, what about Drift’s future are you most excited about?

  1. Vista partnership

  2. Continuing to build our team, culture and brand

  3. Market opportunity ahead. We created conversational marketing and we have now created the conversation cloud.

    • Today’s CRMs will continue to be the ‘system of record’ for our Customers BUT we believe that every relationship starts with a conversation

    • For CRM to deliver on its promise, we need to add Conversational data on every customer interaction and every conversation into the mix

    • That means:

      • Marketers will need to continue to adopt always-on digital engagement strategies to reach their buyer

      • Delivering personalized experiences require a 360 view of your customer with insights on conversation data happening across multiple channels across the full life cycle

      • And IF WE DO OUR JOB right, B2B buyers should never have to ask, or answer, the same question twice

FINAL QUESTION: We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, creating a new healthy habit… what is one challenge you have for the listeners?

Back to the idea of getting comfortable with being uncomfortable. Commit to an experiment:

  • Find one thing that you are going to do before the end of the year to stretch yourself (give a couple personal and professional examples)

  • Brace yourself for the growth it will create


You can follow BSU on Twitter at @BostonSpeaksUp, and recommend BSU guests by contacting

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