Reflections on Two Years of Scaling Growth

This past week, along with finally starting Succession and getting the frozen croissants at Trader Joe’s (two things friends had recommended to me for a very long time that I never did), I had another fun life milestone: On Thursday, I celebrated two years in my role on the growth team at Teladoc Health!

I haven’t written much about my time at Teladoc (formerly Livongo) and I think part of it came from a feeling that I still had much left to accomplish. But as I sit here and reflect Livongo’s growth over the last two years, I’m pretty proud of what we’ve done here.

We’ve enrolled close to 4x more members than when I started, launched more than thirty new campaigns, seen a regularly strong NPS and watched our product portfolio expand more every year. I recently had a meeting with a new leader who had worked with multiple subscription businesses and was positivity stunned at some of our churn metrics.

Is there a bigger lesson out of all this?

While not everything we’ve done at Livongo can be replicated elsewhere, I spent some more mulling over philosophies I’ve developed over the past two years and wanted to share a few top of mind:

1. Do boring things consistently over time.

I’m a huge sucker for a twitter thread on a sexy new marketing campaign or resplendent creative. We’ve had a ton of those. But one thing I’ve learned about some of my favorite work here is that a lot of durable growth isn’t always the campaigns that would make the front page – it’s the work at the proverbial bottom of the iceberg, unseen to the visible eye.

Things like marketing automations and flows running on a regular basis without bugs. Things like checks to make sure data is flowing regularly between platforms. Things like communicating issues to support and mobile teams quickly. Things like running minor subject line tests and tweaking every quarter. Atomic habits built to make the engines squeaky clean. If I think about a hierarchy of needs for a growth team, those are really the things at the bottom of the pyramid right above knowing your audience.

The best campaign we’ve launched will give us a solid week.

The best automation we’ve launched will give us a solid year.

2. Challenge bias and understand how the people you market to make decisions.

Lots of people have asked me over the years how to get better at growth marketing. Usually, my instinct is to send over some books that I’ve enjoyed, frameworks I’ve found useful, or acronyms to know. Traction, for example, is a great book to get an understanding of all the marketing channels out there.

But almost all of this is useless without context. Knowing the entire spectrum of options available to you is one step of a long process that involves understanding the information diet and environment of your audience.

What sites are they using to make decisions? What data jumps out at them in an everyday environment? What do they internalize from other authorities in their life? How often are they even online or opening envelopes in their mail?

Consider that the perspective your company or product has is one of ten that they are currently juggling. Its importance is ephemeral, largely liable to new influences that can arise every week.

Certainly, one way to better understand your audience is by interviewing them or testing out different channels and copy to see what resonates. But the end output won’t always be growth: the end output might just be you slowly challenging your biases.

Your assumptions about the world will shift. The campaigns you create in air-conditioned quarters won’t always be as seamlessly received. The copy you brainstormed won’t always do wonders. Over time, you get comfortable with being completely wrong.

3. Take your data with a grain of salt.

This is perhaps the most obvious one, but one that can often fall to deaf ears in a world where SQL, Tableau, Looker, and the behemoths of big data are screaming for marketers to use it everywhere. Data can fool you.

What people say and report isn’t always what they need. It’s easy to synthesize that “x customers asked for y” and implement a strategy that will use y. But this will often be confusing. People say they want new things all the time. It’s helpful to understand the action-intention gap – the actions people are taking that don’t reflect their intentions. My favorite example comes from Reddit, an anecdote where the team changed the algorithm for recommendations based on recent feeds that someone had gone to, versus the preferences they set when they signed up.

It’s also helpful to look at the context of the data to see whether it actually informs much. If we take a look at all our data from July to December 2020 to make decisions for 2022, for example, we’d look foolish. There were different constraints at play for the entire world. Some of it is still useful, but like everything else, the context is the key.

One useful heuristic I’ve found is to constantly ask myself and my team what the data isn’t telling us. Sometimes it’s a crux for new campaigns – other times, it can simply be a way to derisk our pie-in-the-sky thinking.

4. Balance quick wins with long returns.

My friend Eli Weiss from Olipop has a great tweet I love about retention, thinking about the core of three questions: Why people join you, why they would leave, and what would make them stay forever.

What’s interesting is that none of those questions are ultimately connected to money. Most people are with you not because they want you to get richer but because they have a core human need or experience to unlock and you give it to them.

Yes, I think you could certainly give people discounts and temporary giveaways to curb temporary unhappiness. But the “staying forever” or even staying for a long time means that you have to invest in the things that don’t give you quick wins or even a particular action in return: research studies, supportive SMS prompts, regular delightful content – lots of areas that feel like cost centers without a clear ROI.

Retention is ultimately the things you do that people don’t see as marketing, or particularly promotional. It feels like an extension of your standard experience. Olipop does a fantastic job with this (I’m still learning!) but the core philosophy is something I truly believe in.

Jeff Bezos has a quote about Amazon that I think applies well here: “When somebody congratulates Amazon on a good quarter, I say thank you. But what I’m thinking to myself is … those quarterly results were actually pretty much fully baked about 3 years ago.”

This means a lot of what you do today has to be considered in longer windows. Much longer than the quarter you’re currently in.

It’s hard to write a reflection piece with truly tactical advice and perhaps some of this high-level philosophy isn’t new – but I’ve always considered that not everything is inherently obvious.

Consider this one of many pieces I’ll continue to write as I share more about the work we’ve done and the way we’ve approached growth, with actual frameworks down the road on this blog.



Navigating a Marketing Career Transition

I remember one of the first moments I fell in love with marketing.

It was the Summer of 2015, I was working at IBM as a Strategy Consultant and I was casually scrolling Twitter at work, at the precipice of a growing controversy.

Meek Mill had accused Drake (both rappers) of ghostwriting his songs. Naturally annoyed, Drake responded with a series of cathartic disses and social media became a hotbed of debate around the feud.

Whataburger, White Castle, and Rosetta Stone all made quick jokes on Twitter at Meek Mill’s expense (his response to Drake was not well-received) and enjoyed their share of virality.

But, even as the feud ebbed, I couldn’t stop thinking about it — the internal marketing mechanisms that allowed brands to embrace absurdity, the larger humanization of corporations via social, and why, even as many considered it a waste of time to tweet things that were not related to product or promotions, brands were paying attention to hip-hop feuds.

It was a sticky curiosity about marketing that heightened and drove me, almost four years later, to get my first formal job in marketing.

I never graduated with a marketing degree. I had stints in consulting and product, completely disconnected from marketing teams.

But, this itch to try my hand as a marketer never went away. From that itch, I learned a fair deal about the right behaviors, challenges and occasional luck that comes with a career transition into marketing.

So, this is for you. Maybe you’re a marketer now looking to move into a new marketing job. Maybe you’re doing something completely different but lie awake thinking about the art of Boston Market tweets. Maybe you noticed that the #MarketingTwitter hashtag is an absolute party and you want to join.

Whatever the reason is, consider these questions to make the most out of your transition into marketing.

1. What is My Industry POV?

Whenever you want to transition into a new job, you’re often going to be compared to hundreds of people that likely have experience in that job. The first thing to worry about isn’t a resume, cover letter, or risk assessment. It’s firming down your stance about the world.

There are two ways I like to think about structuring a point of view (POV) on the industry:

  • What is broken in the industry and how do I think it can be fixed?
  • What is working in the industry and why do I believe it will scale?

They seem to be hard questions, but they don’t often have to be complicated.

Most big companies were formed from a similar line in the sand. Shopify wanted to make it easier to start a business from ground zero. Zappos was designed with an emphasis on over-investment in customer experience.

Just like companies, you probably have many things you believe are levers in the world.

  • I believe commerce needs to be more real-time, with live streaming QVC as the next big development in the space.
  • I believe that empathy and human voices in social is the direction more companies need to go.
  • I believe audio will take over video as the next channel for B2C companies.

The point isn’t whether you’re right or wrong. The point is that you’ve thought about the world. That you’re a malleable, emotional human who is curious about where the world is headed and where it shouldn’t be.

It doesn’t even have to stop at platitudes — what brands do you admire? Which voices do you admire? Who do you truly think is moving things forward?

Unlike medicine, law, or banking, Marketing is an industry with little in the way of gatekeeping — an immediate way to become a value-add is to think deeply about why you’re so compelled by it and position yourself accordingly.

2. What Type of Marketing Do I Like?

This one is a fun question because it was the one I struggled with the most. Marketing as a field is huge. Perhaps in the 1950s or 1960s, marketing was mostly characterized by the Don Drapers and sleazy ad men of the world — but nowadays, lots of things can be considered marketing.

There are multiple frameworks to think through the overall landscape of marketing functions —one I love is this breakdown from Arielle Jackson of First Round Review on essential marketing activities: Performance, Product, Communications, or Creative/Brand Marketing.

Image for post

While there is a fair amount of overlap, it brings you to reconcile with some more specifics of your desires than just “Growth Marketer” or “Social Media Coordinator” — the list is a good forcing function to think through your end state.

  • Do you want to work with a SaaS company where you’re focusing more on lead gen (B2B) or more of a customer-facing mobile app focused on generating traffic and downloads?
  • Do you enjoy quick feedback loops, experiments, and data mining, a la paid acquisition and customer journey marketing? Or do you want to work in a strategic role like Product Marketing or SEO, where you may not see results for months?
  • Do you want to work in a more creative and abstract space building a visual identity or more clear-cut deliverables?

As a caveat, this part is frustrating because there’s frankly no magic wand that can conjure up the perfect role for you — it requires a great deal of filtering through job descriptions, chatting with others in those roles, and learning a bit through a combination of in-person osmosis and sporadic youtube videos.

But, if nothing else, start with what you feel you’re good at.

If you find yourself at home with drawing or sketching, consider brand marketing. If you’re most excited by mountains of data, consider direct response. If you’re always on Twitter, constantly looking at what brands tweet, consider social roles. The chart above isn’t a silver bullet — but it’s a good way to shortlist areas you like before embarking on the journey to learn more.

3. What is My Story?

If you’re transitioning into marketing, there’s a chance you started somewhere else and had a fun reason to jump away from it. Once you’ve figured out your POV (#1) and your desired Marketing function (#2), it’s time to bring it home with a good story.

One place to start might be from an unlikely source — Pixar. Pixar’s story spine is a good way to break down your journey and the core reasons behind why you decided to move into marketing. It goes something like this:

Once upon a time there was ___. Every day, ___. One day ___. Because of that, ___. Because of that, ___. Until finally ___.

What does it look like filled in?

Once upon a time there a woman named Christina. Every day, she was working in a day job as an accountant. One day, she noticed a story in Ad Age about a poignant marketing commercial. Because of that, she started to think more about what makes marketing spots great. Because of that, she started to read more about brand strategy. Until finally, she realized that brand strategy was her passion more than accounting and she had to apply for x job at x company.

Of course, it sounds choppy and you would never say it in an interview like I just wrote it above. But from that story above, you were able to somewhat grasp (fictional) Christina’s motivation to become a marketer.

Now, in an actual interview, there is more nuance. You’ll likely have things you liked in your old job — perhaps part of accounting did fill you with joy when you looked at numbers or parts of product management excited you because you talked to customers. That’s also a good thing to note in your story — what do you want to keep and what do you want to change?

If I was to answer the question “Tell Me About Yourself” in an interview,

I’m a self taught marketer that has spent the last few years in accounting. I was really inspired by a Nike ad a few years ago to start thinking about brand strategy — while I loved working with numbers at my day job, I found that I was just spending so many nights thinking about how emotion was fused into commercial ads. I realized I wanted something more creative, that allowed me to balance my analytical skills with thinking through new opportunities for provocative ad strategy. So, this is why I’m here, to pursue x job in x industry.

Hell yeah, Christina. You’re hired!

4. What Are My Risks?

You might think everything is hunky-dory once you have a good story lined up, but let’s face it. You can be a risky hire. Your lack of functional experience might give a hiring team pause and in many cases, most teams are much more likely to go with someone who has done a similar type of role in a similar context.

My friend Nick Dewilde says it perfectly:

Since it’s hard to know whether a team member will work out, most hiring managers cover their asses by hiring candidates with obvious signals of legitimacy. That way, if a hire doesn’t work out, the hiring manager can say, “well, who’d have thought that someone who worked at Google would have been such a bad fit?” In the vein of the oft-cited saying that “no one ever got fired for buying IBM,” no one ever got fired for hiring from Google.

Now, of course, the best way to derisk yourself is to actually learn the skills you need to learn. Based on the role you like (#2), find out which skills the job descriptions require. If your skill gap is SQL, Social Media, or Braze, you know what you need to do to catch up.

But sometimes, that alone isn’t enough — and one way to balance it out is to emphasize areas where you are less risky. Nick shares in his great piece here some risks to consider:

  • Functional risk– Can the candidate accomplish the objectives of this role?
  • Stage risk — Does the candidate have experience operating in a work environment like this one?
  • Culture risk — Will the candidate’s values, attitudes, and habits mix well with the other people on this team?
  • Customer risk — Does the candidate have experience solving problems or creating solutions for our customer?
  • Problem risk — Has the candidate created solutions to solve this type of problem before?
  • Solution risk — How comfortable is the candidate with the process of building and selling this type of solution?

If you have a functional risk (i.e. applying to a social media role without every having done social), consider what risks you don’t have. If you’ve worked in a similar environment, worked with similar types of customers, or even understand the cultural values, those are all legitimate reasons to derisk your hire.

While it doesn’t always work, it does increase the potential for second chances, where hiring managers who abide by a resume will immediately count you out. Nick also gives some great tips in his piece above about ways to derisk your candidacy.

This is an area where I find cover letters especially useful — don’t lead with your risks, but lead with what will change the hiring manager’s mind. As someone who uses social media every day and has worked with traveling agents in multiple functions, I truly believe that x is in my sweet spot.

Walk a mile in your hiring manager’s shoes. Give them less of a reason to question what you bring to the table.

5. How Can I Get Noticed?

Once you’ve done all the above — some serious self-reflection combined with clarity on where you want to go, it’s time to get noticed.

Unlike thirst traps on Instagram, getting noticed as a strong candidate for a position in which you’re fighting an uphill battle tends to be more complicated.

There is an easy way, of course — if you apply to one hundred jobs, you are bound to get noticed by one.

But, one alternative thing I always like to suggest is harnessing your inbound.

What the hell does that mean?

wrote earlier this year in my friend Andrew Exler’s blog about taking an inbound marketing approach to transitions.

When you look at tips for the job search, it’s easy to bias towards activities that have clear outputs: How to write a great cover letter. How to create a cool job tracker. How to use Linkedin to find a recruiter.

While most of them are necessary, they tend to be transactional in nature and often put the burden on you, the candidate, to make the right impression.

You’re the one reaching out to people, finding out the right framing of the cover letter. In many ways, it’s similar to outbound marketing. You have to sell yourself and figure out if someone else is interested.

In most cases, the audience likely hasn’t heard of you and will be quick to reject you.

Inbound marketing flips the script. Instead of cold outreaches, you’re focusing on more low-lift long-term actions that will bring people to you.

This could involve using Twitter frequently, writing long-form posts on Medium, joining Slack groups, answering questions on Quora or even guest blogging for publications you like. If there is a specific domain or type of role you’re applying for, write a new perspective or different type of outlook on that domain.

The key here is that you shouldn’t be expecting any jobs or interviews from inbound activities immediately — your baseline shouldn’t be how helpful it is in the course of 24 hours to your job search. Online presence can take time to build.

As an example, I had been applying with limited success to some roles that required some level of Google Ads experience that I just didn’t have on paper — after writing a Medium article on how one could use Google Ads to make decisions, I was able to complement that experience. That tiny bit of traction was enough to get it into the eyes of product managers and marketers at companies like Uber and Square.

Remember, inbound won’t always get you your next job. But it will increase serendipity, awareness, and appreciation for you — and that can go a long way beyond your next job.


Transitions are hard. As someone who has now transitioned into two different careers, I’ve dealt with every emotion that comes with them — self-doubt, anxiety, apprehension, imposter syndrome — you name it.

But at the end of the day, just remember that your value doesn’t get set in stone when you’re eighteen.

You’re allowed to grow, evolve, and become wide-eyed and awe-inspired by new industries and functions, whether this happens in your late 20s or 30s.

You’re allowed to dream of new ways for the world to exist, without your past experience and decisions being the litmus test for the value of those dreams.

I hope, if nothing else, this gives you some more areas to think about, to make your transition feasible.