Startup Swingers

Growth executives swap companies for a day

Apr 18, 2017 · 7 min read
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Photo, Twenty20

Last month, I pitched a fellow growth executive on an idea: let’s swap companies for a day. We did — here’s the story:

The realization:

I met Matt (Head of Growth, The Black Tux) at a coffee shop on Wednesday, Feb 22nd. A short 30 min conversation about podcast advertising and SEO quickly turned into hours of bantering around all-things-growth — how to work with designers, building a growth-minded culture, hacky ideas, etc. I started thinking in the back of mind — holy shit…while we work for different startups, our work lives are basically the same.

I realized three main things:

  1. Matt and I could easily switch jobs and probably have similar success.
  2. Most companies keep their data hidden — ensuring that they’ll never be able to get help from others.
  3. My biggest weakness is not insufficient skills or under-thinking. It’s that I might be so in the weeds in my own business that I can’t see my own blindspots.

So I pitched…

I’ll come to your office for an entire day and provide feedback on your blindspots. And vice versa. You in?

I went first.

I showed up on a bright, sunny day in Santa Monica at their office.

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View from outside the office of The Black Tux

A few days previous, Matt shared an overview of his company’s data & business. So I had done my homework beforehand. The morning was spent going much deeper — I asked tons of questions on topics including, but not limited to, margins, virality, seasonal buying behavior, previous hires, discounting, email marketing, acquisition, personas, LTV, branding, conversions, etc. I took in every piece of knowledge about the team and business I could in a 3 hour sprint. During lunch, Matt opened up about interpersonal challenges — how best to work with creative teams, engineering teams and company stakeholders. It was fascinating — mostly because I have struggled with literally the exact same challenges. One challenge that stuck out was: given that meetings can be a time suck, how could he find more time in the day for exploration, strategy and ideation.

In the afternoon, I put my headphones on and wrote.

It ended up being a 6 page document…I broke it up into:
1) Macro thoughts on the business
2) Thoughts on the how Matt could gain more time & headspace
3) Growth strategy feedback
(what I’m seeing, what’s great, what’s missing, etc)
4) Tactical ideas for unexplored areas.

We then spend 2 hours reviewing the document with clarifications, questions and debate on ideas/strategies. Honestly, I was very impressed with Matt and the company. They have a solid handle on how to grow their business. The blindspots I saw were around the edges — areas that they had previously thought about, but forgotten to re-access for a while. I called these “mythologies”. Every company has them — someone, at some point, who seems smart, says something…and then others repeat it as if it’s truth. It seems logical, it seems right, it seems true. But, in my opinion, there’s hidden gold in breaking down mythologies and re-testing previously held “beliefs” — for growth tactics, personal, and company building.

Matt’s note to me afterward:
Thanks again for coming in today. I found it incredibly helpful to get your perspective on opportunities we have. Potentially even more valuable though was to get a fresh perspective on some of the more nuanced aspects of things our company is grappling with at the moment internally. Really enjoyed getting your take.

So, how did the day feel for me?

Honestly, I was fucking exhausted. Like a sponge, I soaked up everything I could about their business. I let myself get lost in the weeds of their tactics, their organization and their company. I definitely needed a good night’s sleep after that. Besides that, it was a ton of fun and I learned a lot — seeing into someone else’s growth stack, team organization and mindset was incredibly powerful.

He went next.

The next week, Matt arrived at our office.

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Twenty20 office

Similar to my experience, I gave Matt a business overview to digest before arriving. Read that document here =>

We spent a couple hours diving into the data. He also got a chance to observe our weekly growth meeting — where we review our most recent information and plan our week’s sprint.

I realized the main knowledge gaps between his business and ours were 1) an understanding on how B2B is different than B2C (more targeted personas, mapping organizational decision making, etc.) and 2) how to look at the health of a MRR business. He picked it up quickly and was off to the races. After lunch, Matt spent some time evaluating what he’d seen and writing down his thoughts.

Around 4pm, Matt shared his notes — the biggest items were:
1) Time spent building out weekly reporting seemed a bit excessive.
2) Invest in testing “aha” moment => activation flows
3) Keep focused on SEO & word of mouth
4) Keep testing Pricing & Packaging
5) Organize around a more clear growth framework
Read Matt’s entire document here =>

For me, the most interesting feedback was around nailing down a better growth framework — essentially, building a simple math equation that allows us to plug in an idea and output the expected revenue impact. We spend the remaining time digging into what that framework should look like:

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Matt at the whiteboard in Twenty20’s conference room

Overall, Matt provided valuable feedback into our blindspots. In general, some of the ideas had been considered in the past. However, because of momentum and mythologies, we’ve procrastinated testing some those ideas. Since then, we’ve added them into our backlog and we’ve been using the growth framework to guide our impact scoring. Pretty fucking cool.

Matt’s note to me afterward:
At first I was nervous about whether I would even be able to add any value in such a short time at Twenty20. I felt that my experience in direct to consumer e-commerce would be of little help as I jumped into the world of a two-sided marketplace with a growth team that’s largely focused on the B2B side. But what I learned over the course of the day there is that, irrespective of the business model or industry, Growth is simply about dissecting the system of how a company makes money (or acquires users) and identifying the levers with the most opportunity to accelerate it. Once I was able to wrap my head around the fundamentals of the business the rest fell into place.

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The interesting thing though, is that as much as I’d like to think my insights were valuable to Micah and his team, I left the day feeling as though I was the one who had learned a ton. If you’ve ever studied a foreign language and then been fortunate enough to travel to a country where that’s the primary language spoken, that’s kind of how I felt at the end of the day. I had to consciously stop myself from thinking in the familiar patterns I’ve grown used to and force my brain to work and think in new ways. I was very tired when I got home but all I could think about were the many things I wanted to bring back to my team and apply to how we work.

Key takeaways from Startup Swinging:

1) Is it weird?
The idea seemed a bit weird initially. I wasn’t sure how my company or his would react to the idea. Ultimately, our respective leadership teams were on-board. And once it happened, I think they were jealous. The truth is that none of us are perfect or have all the answers. We always need someone to spot our blindspots…and sometimes it’s helpful to get it from outside the company.

2) How do I make swapping productive?
It was vital that we shared very detailed information before coming in. While 8 hours sounds like a lot, it isn’t — it flies by. Do your homework and dive in quickly. Most importantly, give written feedback first, then discuss after — sharing your thoughts in person takes too long.

3) Would you do it again?
Fuck yea.

Final thoughts —

It’s extremely valuable to get detailed feedback from other smart people in the startup community. So why do startups keep their data, company progress and personal challenges hidden?

Last year, we decided to open up our Twenty20 story to the world and amazing things started to happen. We saw incredible alignment internally, revenue growing faster than ever, a flood of emails from interested investors, employees taking ownership over major company initiatives & much more. Startup swinging, for me, is just the beginning of opening up our internal data to smart people & leveraging others to help us grow. Throughout 2017, we’ll continue this effort.

Thanks for reading! :) If you appreciated it, hit that heart button below. It helps other people see the story.

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Written by

a curious human— formerly EIR @TubeScience, VP Growth @Twenty20, Marketing @LivingSocial, Writer @TechCocktail

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.


Written by

a curious human— formerly EIR @TubeScience, VP Growth @Twenty20, Marketing @LivingSocial, Writer @TechCocktail

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

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