Notes from Iterable Activate 2022 in San Francisco

I attended Activate in San Francisco held at the Marriott Marquis. It was a fine time. I gravitated toward high-level strategic talks in-person. I take a look

Most insightful talk: Women Language + Power and Standard Communication by Susannah Baldwin

When I walked into the room vaguely labeled “professional development” session I was late so I hurriedly took a seat at the side of the room. After I got settled and composed I realized I was one of two men in a room of one hundred women. Ooops! I felt way out of place but I stayed in the room and happy I’m happy I did.

The speaker’s point was that women are taught at an early age to speak in a soft or indirect manner. To reach the upper echelons of But that’s not

Many Useful takeaways : Find Your Target: Reaching Different Personality Types Without Flooding Your Marketing Channels by Tim Hemingway, Havas Media

Broadening my horizons: Presenting with Impact by Susannah Baldwin

Reforge notes: Retention & Engagement

Rough notes while I go through the Reforge Summer 2022 program on Retention & Engagement.

4 Strategies to increase ENGAGEMENT

  1. Add Use Cases
    1. Uber
      1. start with going to airport
      2. add going out with friends
      3. add commuting to work
    2. JIRA
      1. start with bug tracking
      2. add product releases
      3. add project management
    3. Calm
      1. listen to sleep stories
      2. add journaling
      3. add coaching
  2. Increase usage frequency
    1. Metric is weekly active user (all are weekly actives)
      1. 1x/week
      2. 4x/week
      3. multiple times/day?
  3. Increase feature usage
    1. Expand breadth of features does individual use.
      1. User 1: Sleep stories & music
      2. User 2: music & Daily Calm & Journal
  4. Increase intensity of usage
    1. amount of time per use? (listen to Calm music 5hrs/session)
    2. $ spent
    3. # actions per use (?)

Add Use Cases

In what ways can we expand the number of uses for subscription apps that I am trying to improve?

Calm use cases

  1. Bed time
  2. Focus during work/study
  3. Leisure during commute
  4. Consistent daily mindful practice (advanced)
  5. (expand to) measuring personal growth?
  6. (expand to) handling anxiety in-the-moment

TTS Inc. use cases

  1. Leisure reading fiction
  2. Reading textbooks
  3. Reading work documents
  4. Proof-reading, editing, review
  5. (expand to) studying, taking notes on subjects.
  6. (expand to)

How we saved $15,000/month and increase conversion 300% with Lifecycle automation.

Summary

On my nights and weekends I worked with a startup to automate their Lifecycle email program. Within 3 months of working together the company saved $15k/month and increased new trial subscription starts from 50 per week to 200 per week.

Weekly sales revenue growth before Lifecycle and after. The different color bars and coupon discounts that I tested to optimize pricing.

How did they achieve this?

  1. Prioritized revenue automation as our Q3 goal
  2. Eliminated any initiatives not directly related to the Q3 goal. (Such as brand marketing)
  3. Identified events critical during the customer lifecycle that needed to be sent to the marketing platform.
    1. new user sign up
    2. paywall abandon cart
    3. trial and paid subscription churn (user cancellations or time-based expirations)
  4. Partnered with the engineering teams to get the lifecycle events flowing into the marketing platform of choice. In this case, Intercom.
  5. Monitored and tested the data coming from engineering.
  6. Launched Lifecycle programs

Company Profile

This startup is a subscription-based text-to-speech productivity tool available on the web, iOS, Android, and as a Chrome Extension. To keep things simple, I’ll refer to this startup as TTS Inc.

TTS Inc. is a small-but-mature company that the CEO started in dorm-room in his dorm room a number of years ago. The company had mild growth and accelerated when they got into aggressive paid advertising The team is currently ~100 people, including contractors like myself.

TTS Inc. offers a freemium product. The free tier is the core text-to-speech product with a limited feature set. For example on the free tier the reading speed is capped at 150 words per minute while the Premium tier listening speed is 900 words per minute. 900 words per minute sounds crazy but it’s possible to comprehend.

Most users upgrade to the Premium tier subscription by joining a 3-day trial. The trial requires a credit card and converts to a 12-month subscription, renewable annually.

TTS Inc. reached out to me because they wanted to get their martech stack aligned to allow them to scale and automate their Lifecycle marketing campaigns through email, push and in-app messaging.

Execution

Step 1: Prioritize revenue automation

Lifecycle marketing started as a component within the TTS Inc. Brand marketing team. Brand marketing had two goals.

(1) Increase revenue with Lifecycle
(2) establish a consistent brand identity.

Having these two goals caused TTS Inc. to make some missteps that harmed them. Part of the Brand team’s plans for the future was to send a highly stylized, beautiful weekly email newsletters to the active user base. Keeping that future brand-focused state caused me personally to get distracted because I was trying to push their marketing infrastructure to support for a future that had not been realized yet. For instance, I was advocating for us to switch to an email service provider that would make sending high volumes of email easier and cheaper than their current system.

By the end of my first two months we missed our revenue goals. We were getting single-digit trial starts per day. Not good. Our lifecycle program was abject failure.

Since we missed our goal, leadership chose to eliminate the Branding team except for Lifecycle. As a regular listener of Alex Hormozi’s podcast I now understand his view in episode 382: branding is a game the big companies. During this time TTS Inc. was not at the stage where it could spend a lot of money on activities that did not have immediate measurable impact on sales – branding is one of those. Brand-related activities included surveys, newsletters, and highly stylized one-off email sales announcements were a distraction and difficult to attribute to sales.

Now my priority was clear: improve LIfecycle revenue.

Step 2: Eliminate all non-core activities

To become hyper-focused on our one goal we had to stop doing non-sales activity. We dropped doing branding which in turn allowed us eliminate other products.

WE eliminated unnecessary software

TTS Inc. had two marketing-related systems: Drip and Intercom.

TTS Inc. was spending $12-$15k per month on Drip — an email marketing platform designed for small-to-medium sized business. TTS was getting very little out of Drip because they had not dedicated serious engineering resources to get their data synchronized with their own user database.

Having two systems made things worse because engineering didn’t know which systems needed which event? If both systems needed the same events or data there would be some minimal amount of maintenance work involved with keeping things accurate on both platforms. It was an all around mess.

With branding removed from the priorities, leadership made the decision to eliminate Drip from the tech stack. Canceling the drip account saved the company $10,000-$15,000 per month.

WE Eliminated resource-heavy activities

Understanding that Intercom is not well-suited to sending a lot of email (too expensive, bad interface) we pared down email production down to just one person to do all the work with minimal concern for visual appeal.

Brand-focused email:

4 people, 1 week

  1. Mockup email (Lifecycle)
  2. Write email copy in the brand’s voice (copywriter)
  3. Design a pretty email (email designer)
  4. Build the HTML email (HTML developer)
  5. Set up the automation (Lifecycle)
  6. Launch the email (Lifecycle)

Ugly email:

1 person, 2 hours

  1. Cobble together some copy text (Lifecycle)
  2. Build HTML email – basic styling (Lifecycle)
  3. Set up the automation (Lifecycle)
  4. Launch the email (Lifecycle)

In the weeks after eliminating the “pretty” emails I have found that sales have not been noticeably harmed. In fact, email-to-trial conversion rates may have actually gone up.

Step 3: Identify critical events and data to use in the marketing platform

Automation was difficult regardless of marketing platform. Neither of TTS Inc.’s marketing platforms were integrated with the business’s data pipelines. Intercom, in particular, was missing a lot of critical account and subscription-related information. In order to get Intercom operational quickly we stripped down our requirements to a set of eight subscription-oriented Lifecycle events that could be the bare minimum backbone for direct sales messaging.

  • New user created an account
  • User saw paywall but did not buy (abandoned cart)
  • Trial started
  • Trial expired
  • Trial canceled
  • Subscription started
  • Subscription expired
  • Subscription canceled

In my experience the subscription events are difficult to get because subscription data comes from many sources: paypal, stripe, apple, Google, etc. The team responsible for managing subscription did a fantastic job in delivering subscription events to Intercom on an hourly basis.

Step 4: Partner with engineering

TTS Inc.’s leadership did an outstanding job of aligning engineering resources to prioritize Lifecycle. This was easy because the company’s engineers are naturally business-minded. Leadership communicated clearly and directly to the engineering teams that Lifecycle’s goal for the quarter was to start making money and to prioritize Lifecycle requests over other initiatives. Being business-minded folks, the engineers were also innately eager to help us get these projects off the ground.

We met with the engineers a few times to discuss our minimum needs and the engineers added in some things that would make reporting easier for other departments (such as ad-buying group, or finance). Since we agreed on the set of events ahead of time I was able to start building the user messaging journeys in Intercom in parallel with the engineering data team’s work.

There were many teams involved in this work:

  • Platform engineering did the work to synch subscription data to Intercom
  • Web engineering had to start sending new user signup events to Intercom
  • Product management team found flows that broke and needed to be migrated from Drip to Intercom

After a rapid 3-4 week development cycle engineering completed their work and we were ready to turn things on.

Step 5: Monitor and test the data

Once engineering launched their respective work we had to double check their data.

For the first few days of the launch we observed that many events were under-firing. Engineering found that in many cases the user’s identity was not correctly being established before sending the data to Intercom. This is not necessarily name & phone number identity — i mean database unique id which is usually a jumble of letters and numbers.

This is an important bug. Marketing systems don’t magically tie data to a user. Engineering has to put operations in the correct order. If you do not have the correct order events that do not have a proper user ID will go to a black hole.

Correct order

  1. user sign up
  2. wait until user id assigned by backend system
  3. establish connection to marketing platform
  4. send events

Incorrect order

  1. user sign up
  2. establish connection to marketing platform
  3. send events
  4. user id assigned by backend system

This is an engineering thing but it’s important to know. In one bug we found, the web app was sending a “new user signed up” event before the user’s ID was established on TTS Inc.’s database. So we were getting a lot of events but no user data. The web app made a small code change to wait until the new user’s id was established on the backend before sending the event data to Intercom. After that we were able to send messaging to new web users.

This is the case for many marketing platforms and if you are losing a lot of event data or getting a lot of “anonymous” or “unidentified” users in your SaaS platform this might be the issue.

In summary: order-of-operations is important. Your engineers need to know that the user’s ID needs to be established before logging any events to your marketing or analytics platforms. (Amplitude, Segment, Iterable, Braze, Intercom, Drip, etc.!)

Step 6: Launch the Lifecycle programs

This is the easy part! Once the data is live and flowing we are free to experiment using the marketing platform.

There is no secret sauce here. Other subscription apps and e-commerce websites follow a similar pattern of direct-to-consumer sales. We mapped the events directly to their own set of emails.

  • New user: send a welcome series of emails
  • Paywall: send abandon cart email
  • Trial expired/canceled: send a win-back email
  • Paid subscription expired/canceled: send win-back email

We launched the lifecycle automations and by the first full day of emails upsells were 2x the previous day. Over a 3-week period the average weekly web sales volume was three to four times the typical week.

Further refinements that we made:

  • built a customized and editable web landing page to test and measure conversions
  • offered discounted plans
  • sent in-app messages in each workflow

Conclusion

Although it was a bumpy ride at first, TTS Inc.’s marketing automation stack is well-situated for growth. Within the first week, their lifecycle sales automation performed well far beyond my expectations. Now that they have had consistent sales baseline they can begin to experiment with branding and other marketing tricks to boost conversion performance.

The MVP for a multi-million dollar product built on Google Sheets and Iterable

In April 2020, I helped launch Calm Sleep School, which was an early prototype of the coaching product that later became Calm Sleep Coaching (Sept 2020-2021) and continued to grow into what we now know as Calm Health.

In late 2019 Calm hired a Chief Medical Officer to spearhead the company’s initiative to move into the mental health realm. The Chief Medical Officer-slash-head-of-sales came to us from a mental health platform that sold as a business-to-business product for large companies to offer therapy as an employee benefit. His Big Idea was for us to create a similar product that wasn’t quite therapy-level help but would address broad problems that affect mental health (i.e. sleep, diet, physical health, stress, anxiety, etc.). Leadership settled on sleep coaching in part because our CEO admitted that he was having trouble sleeping at night so he could be the Founder AND a customer.

The idea was simple: professional sleep therapists would conduct a series of 6 one-on-one video coaching calls with individual students to identify issues that were causing poor sleep and to provide a personalized sleep plan for the clients to follow. An example sleep plan might be to stop drinking caffeine after 3pm, turn off the TV at 9pm, and go to bed consistently each night.

The design concept was beautiful (see the Launch Email). Our product designers contracted a professional illustrator to create one-of-a-kind art with everything in a deep sleepy purple. Design was top-notch.

Calm Sleep School had some serious challenges. Engineering would commit near-zero resources to building the system. Since this was only going to be prototype with unknown value, leadership would not commit significant development time because the engineering team was already stretched thinner than a spider’s web.

Engineering worked on these components:

  • One backend engineer to create the SKU and hook up the Stripe billing mechanism. I believe she accomplished this within one sprint.
  • Frontend web team built a landing page
  • Frontend web team built the checkout page for customers (students) to pay via Stripe (via the billing backend)

Lifecycle (my team) was responsible for all of the onboarding and this is where I am quite proud of our achievement because I was able to build the onboarding AND a coaching management system using Google Sheets, Google App Script, and Iterable. (My equivalent of duct tape and paper clips.)

Launch Email

Sleep School Onboarding

Before onboarding could begin people would arrive on the landing pages and checkout built by engineering.

Upon successful purchase, a Welcome email to explain the product and inform the new student the details of Sleep School.

Using Google App Script I scripted the user intake form to take several actions:

The Welcome email pointed to a user intake form (Google Form) which asked a series of questions to understand why the new student needed help sleeping.

(1) It emitted an event to Iterable so that we would have a record of user’s progress.

(2) It sent an email and logged a row to our internal teams to know a new student signed up.

The coaching team would manually match the new student to one of six Sleep Coaches. The match of sleep coach to student was logged on the sheet. With the match made we would send an email with the introduction of the coach with name, picture, and bio.

(3) The script had to copy a Google Drive folder filled with a handful of assets that coaches used for taking notes and sharing reports with the students.

Since each student needed to have a unique Sleep Journal I logged the folder, Sleep Journal Google Form, and other things into the Google Sheet as well as Iterable. By saving the Sleep Journal Google Form ID we could send an email to each student that had a link to their personal Sleep Journal.

After students’ 7 days of journaling they would have a one-on-one Zoom call with their Sleep Coach and the coaches would then carryout delivering the remainder of the Sleep School experience.

Sleep coach match

We launched Sleep School slowly by sending batches of 10,000 emails to existing Calm Subscribers so that we could pace the flow of student enrollment and not overwhelm the coaching staff. Our goal was to sign up roughly 100 students to complete the 6-week course which we were able to accomplish. Students were satisfied with the program! I don’t think we had to issue any refunds related to the quality of the course. Some folks canceled because they didn’t realize the program cost around $600 USD. In further sales development our Head of Sales had inked a deal with some corporate clients to

As I said before, this was an early prototype. Leadership was encouraged by the product so they decided to build Calm Sleep Coaching product which was staffed by 1-2 full-time engineers. As of 2022 that product further evolved into Calm Health which has a full staff of 12+ full-time engineers dedicated to bringing mental wellness as an employee benefit for thousands of companies and tens of thousands of employees!

Black Friday 2021 notes

I identified a profitable segment combining app usage and sales data from the previous year

I found a particularly profitable segment of users by looking cross-referencing app usage and purchase behavior. For the Black Friday 2020 campaign we sold far more high ticket items to people who had used the app for 12 consecutive months (the size of the circles represent # plans purchased). It helped us send our most active users our best deal. (High price but high discount)

Bigger circle = more sales. X-axis is consecutive months of activity.

Spreadsheet command center

To keep track of the 60 campaigns I built out a spreadsheet to track the different offers and email template modules to include in the campaign. Different segments received personalized offers (pictured) based on analysis from our Data Science team that found the optimal offer according revenue per email sent.

Each cohort, the day of the campaign, and the sales modules to be offered to the recipients

Landing page switch led to 40% conversion improvement

Toward the end of the campaign I created an A-B test for the email click’s landing page.

You should notice that the original page is a very simple credit card page. Because we were advertising a Black Friday time-limited sale our logic was to collect payment as quickly as possible.

You will notice that Treatment version has a lot more information. It has a big hero image, some science facts, a product comparison checklist in the middle, and testimonials on the bottom. Our product & engineering team had refined and tested this landing page for peak performance earlier in the year but we had never tested these two variants against each other within the context of a holiday sale.

The A-B test showed 50%+ sales conversion improvement over the 3-day observation period for the campaign. I wished I had tested these two landing pages earlier in the campaign!

I believe that part of the reason the page performed so much better is that we only sent this page to users who never subscribed before. These people barely know what Calm is so I believe that having the extra information on the page properly educated the returning inactive users and clearly did a better job at explaining the value of the Black Friday deal that we were offering them.

Next year I’ll be sure to compare the two variants across broader audience (churned, current paid, etc.)

Original
Treatment

Treatment landing page (green line) outperformed for duration of the sale
52% improvement & statistically significant

Patterns in engineering job hunting

Newer job seekers and people not may not be familiar with the common job hunting/candidate recruitment process. I’ll try to explain the commonly used process that I’ve noticed to be used by many companies in the Bay Area.

Phase 1: Finding potential jobs

Roughly in order of effectiveness:

Internal Employee Referral – warm

If you happen to know somebody who works at a nice company and you’d like to join them there reach out! Take them out to coffee or get lunch or just IM chat with them. It really depends on how well you know the individual. It’s probably useful to be upfront that you’re open to new opportunities early. If your friend or co-worker is on a team that is actively hiring, you’ve got a warm employee referral on your hands! Going to interviews on a warm employee referral is so much better because I’ve gone to an onsite interview — completely blown half of the questions — and still gotten the job because I knew people that worked at the company who were able to vouch for my real work abilities that aren’t always apparent in a marathon of 1-hour interviews. (Plus jangled nerves)

Internal Employee Referral – cold

You contact your friend at Company X but her group isn’t hiring right now. It’s still OK to go into the pool of general applicants. This isn’t as effective because it could be a while before you hear back from anyone. Effectively you become the same as any other non-referral applicant but at least you’re in the system and maybe down the road your friend will get a referral bonus because you got hired through her efforts to get you into the system.

Internal recruiter cold-email reach out

A recruiter sends you an email or a LinkedIn InMail. Respond to it and you’ll at least get to an informational phone call. That is useful because at least you can reach out to the recruiter later to confirm that you were seen and acknowledged as a human being. You do exist and your resume had something worthy of attention!

LinkedIn network status update

People say they are hiring all the time these days. DM your LinkedIn connection and ask them to refer you into their recruiting system. They can leave notes about you and it will put your resume toward the top of the list. It doesn’t mean you will get called back but it increases the likelihood that your resume will have been seen and reviewed at least for 4 or 5 seconds. Which is better than the methods below.

Direct application on Careers section of website

Surprisingly, I find myself sending people to the careers page of places I’ve worked many times. At startups, the CVs do get reviewed by people internally. Larger companies are less effective

3rd party recruiter cold-email reach out or cold call

Very often these recruiters have very poor information on the job. GuruJobs or Robert Hat. It does not appear that they have a direct connection with the hiring manager. Unclear to me how effective a job hunt will be through these sources.

Big Job Board job application (LinkedIn, Indeed, Monster, HotJobs, Dice, Craigslist)

By far job boards are probably the worst way to find a job. I don’t care what all the commercials say. Don’t waste your time crafting a personal statement or cover letter on these job boards it’s basically pointless. Go directly to a company’s website and submit your resume there instead.

Phase 2: figure out which company is the most interesting

If you can get past the resume screen, companies will start with an informational 30-minute call with a sourcer/recruiter responsible for filling the position. Recruiters are friendly professionals that specialize in talking to other people. They are usually not subject matter experts in engineering, marketing, or whatever your field of work may be.

They are experts at identifying sifting out legitimate experience and from bullshit. In the informational call the recruiter’s job is to describe to you the responsibilities of the role and gauge your interest in the position. Then they sniff out whether you correctly speak the jargon and match the profile of the type of candidate that the hiring manager wants (years of experience, projects worked, interests).

Recruiters will tell you about the company’s mission and culture. They won’t know the company’s five-year product roadmap. They won’t typically know the specifics of the day-to-day of your role. They will be able to tell you is the manager is looking for a specialist or a jack-of-all-trades? How big is the team? Do they prefer Ivy League graduates? You still need to do homework about the company so that you don’t ask blatantly un-researched questions about the company.

Phase 3: Interviewing

After you have talked with the recruiter and sufficiently proven that you are interested in the role, the company, and the department within the company you are ready for some interviews. This is my knowledge of Silicon Valley-style tech interview process.

First, you will have the phone screen interview. Recently interviews have moved off of the phone and into Zoom with screen shares and social coding platforms. The phone screen should last 30-60 minutes and administered either on phone or Zoom where you’ll talk to a fellow engineer who may be a member of the team that wants to hire you. Usually the interviewer has pulled a pre-determined problem pulled from a bank of questions that the team has agreed to use. You will be asked to solve the problem within that 30-60 minute period. You do need to be able to finish the interview within the allotted time because the interviewer probably has another meeting right after your call. Phone interviews are supposed to be “easier.” After many years of dealing with this interview pattern, I know that if I find myself barely getting through the phone interview I know that the on-site is definitely going to be a waste of time for everyone involved.

I think I’ve been asked these “basic” items than a few times on a first-round phone interview:

  • What is a closure?
  • How do you reverse a list?
  • Code a basic HTML/CSS page that can do X,Y,Z

The “on-site” interview (should change the name now that Zoom has become prevalent) is where you line up a day’s worth of interviews and teams grill with 4+ different exercises in varying subjects. For example you might get the abstract puzzle interview, followed by SQL exercise, followed by an algorithm test, followed by a system design discussion. Having failed at literally dozens of these interviews it’s hard to believe I actually ever was able to survive in Silicon Valley for 15 years as an engineer. I do know why I never made it to FAANG because I am pretty horrible at all of these types of interviews and really can only pass the hands-on “let’s build something practical together” type of interview. I don’t have any tips on how to pass these interviews. However, expect to see something like

  • Traverse a graph to do something
  • System design something for millions of people. Web servers and load balancers and calculations of throughput will likely be involved. (I wouldn’t know because I don’t pass these tests)
  • Do something recursive, probably with sorting. It definitely needs to run better than O(n^2) or O(n!)

Phase 4: Results

Now this is the shitty part. Sometimes you might do pretty good and pass all the technical aspects of your interviews. Even if you pass all the tests, you may only have 5% of landing the job because you are competing against 20 other candidates just like you who also passed the tests. This is especially true at a hot startup or a FAANG company.

After your interview all the people you met with will convene in a meeting to decide your fate. The more people you interviewed with during the process, the more chances there are for one of those interviewers to say “no.” That’s not a death sentence but it does hurt you a lot. You would never know it but that’s what goes on after the interviews are over. I have been on hiring panels of 6 people. Sometimes 5 people say “medium yes” and 1 says “strong no” you’re toast. But if you get 5 “strong yes” and 1 “medium no” you still have a chance — that “no” can be swayed.

This is just me, but receiving a “Thank you” note from a candidate does nothing to sway me in any direction for or against you. Experts suggest you to do it but, honestly, the second you walked out of the door or hung up the Zoom I already know if I’m going to vote for you or against you. An after-interview email is meaningless and chances are I probably won’t see it at all because I don’t read email. All of my work in JIRA and Slack.

At the end of the day, if you get rejected from a job application know that it’s not necessarily something about you. There are infinite factors during an interview that are outside of your control that have nothing to do with you. Just be as authentic as you can be. Answer questions as honestly as you can. Be “right” or “correct” on factual questions as much as you can be. Then be prepared to do at least 10+ full interviews (phases 1,2,3,4) before you receive an offer.

How I manage my Iterable Catalogs using Google Sheets

Calm’s dynamic emails leverage the Iterable Catalog feature extensively to keep campaigns evergreen and easy to maintain. I use it for a variety of use cases:

  • Email localization strings. Calm serves content in English, French, Spanish, Japanese, Korean, Portuguese, and German.
  • Content calendars. Calm has a variety of content that releases on a regular cadence including the Daily Calm and the Daily Trip.
  • Follow-up lessons. For special programs we send messages that remind listeners of key takeaways, lessons, or review material.
  • Top N lists. The most recent Catalog I added allows others to curate lists of top/new/hot/trending content.

I have been most tickled with my most recent effort to store Top-N lists (Top 10 newest music, Top 10 most popular, Top 5 fill-in-the-blank) in our Catalog because it streamlines our process for creating ad-hoc special announcement emails. Creating this did not require a lot of code and makes me wish I had thought of doing this earlier.

Google Sheet as Content Management System (CMS)

Using a Google Sheet shared with my colleagues allows us to have a mix of curated and automated feeds controlled by different:

Automated feeds:

  • the newest Sleep Stories for each language
  • the newest Music releases for each language
  • the newest Meditations for each language
  • 3 content types * 7 languages = 21 individual feeds

Curated feeds

  • featured English new releases
  • English-language blog content
  • special blocks for other departments to provide content (b2b, marketing, product, engineering)
The Sheet Tab name “konewSleep” becomes the name of the data feed in the Catalog. The sheet columns headers are key names of each object.

The Catalog

See how the Google Sheet columns map to JSON key names.

Retrieve and Render Iterable Catalog Data

Using a known key, such as ennewSleep I am able to retrieve the appropriate content for Korean language new Sleep Stories.

{{!-- look up new Sleep Stories in English (en) --}}
{{#catalog "Datafeeds" "ennewSleep" as |datafeed|}}
{{#lookup datafeed "programs" as |prog|}}
<h1>{{{ prog.title }}}</h1>
<p>{{{ prog.description }}}</p>
<hr />
{{/lookup}}
{{/catalog}}

Basic HTML result would be

<h1>Sleep story title 1</h1>
<p>Description of story 1</p>
<hr />
<h1>Sleep story title 2</h1>
<p>Description of story 2</p>
<hr />

Addendum: Roadblocks along the way

My initial intent for this project was to lean on Iterable Datafeeds and Google App Scripts to provide my dynamic data. I created a Google Apps Script to create a web app that would grab some API data, package it up into a more email-friendly rendering payload, and return JSON. I ran into 2 major problems while trying to set this up which eventually led to my Catalog solution.

First, I found out that I cannot change the user-agent HTTP header when using the UrlFetchApp library. UrlFetchApp sends something like Google/app-script-client when doing its HTTP fetch. I needed control of the user-agent header to pull the different language content from the API. My solution to this was to set up a free Netlify account that would proxy a request Google -> Netlify -> Calm. I created the proxy as a serverless function. This only took a couple of hours thanks to Netlify for its very developer-friendly deployment tools.

My second problem is that Google App Script only serves a few requests per second (expected). I was expecting to lean on the caching option in the Iterable datafeed fetcher. My theory was Iterable would hit my endpoint once and cache the response for 1 hour as described in their documentation. Despite several attempts at configuring the templates and datafeeds I could not get Iterable to cache my feeds properly. During campaign send time Iterable would hit my Google App Script hundreds of times per second and fail out due to rate limiting problems.

Figuring that the caching roadblock would be unsolvable on my own, I decided to use the Iterable Catalog solution instead. The Catalogs are useful because I don’t have to worry about maintaining uptime on the services but not as nimble as a API solution because I have to constantly sync my Google Sheet to the Catalog(s).

Do Gmail promotion cards improve email performance?

Long story short: gmail promotion cards did not have statistically significant positive impact on our Black Friday email campaign.

My first year being on the retailer’s side of Black Friday was 2019. It was a harrowing experience due to lack of experience and being new to my job. We hectically threw together our Black Friday campaigns around 3 weeks before Thanksgiving: copy writing, design, QA, pre-testing, and identifying segments for the biggest revenue week of the year all done as quickly as possible. This is not an experience I recommend. In 2019 I knew about Promotion Cards but since we had a very short timeline to work on the emails and I didn’t have time to test the Promotion Cards. In 2020, we started planning in early October. Unfortunately I forgot about Promotion Cards until the Black Friday week. Remembering that I wanted to test the cards in 2019 I scrambled to incorporate them into a handful of our early campaigns sent on Tuesday of Thanksgiving week to see if the cards would be able to measurably increase sales conversion rates for our biggest email sends running from Black Friday to Cyber Monday.

I tested the promo cards on 4 different emails with volume around 4 million people. I looked primarily at 2 metrics: open rates and send-to-purchase conversion. I know open rate is a vanity metric — call me vain! Promotion Card’s best performance garnered +5% better open rates (stat sig) but send-to-purchase conversions were -1.2% worse than control (not stat sig). The Promotion Cards lagged in both metrics in other campaigns as well and could not achieve statistical significance for purchase conversion in any test. Since I couldn’t get stat sig on the sales I decided to take the easy road: no Promotion Cards for the remainder of Black Friday 2020 campaigns.


What are Promotion Cards?

Several years ago Gmail came up with the “Promotions” tab to automatically separate out marketing emails from people’s inboxes and into a separate folder. Marketers freaked out because the Promotions tab, essetially, is a Spam-lite inbox. All the marketing riffraff ends up lost in the outer limits email equivalent of the axe-murderer-creepy cluttered basement or the spider-filled attic. The Promotions tab on Mobile devices is especially challenging because the tab lies within a menu drawer.

I find out about new GMail features from the Product Managers that work at Google. Both at Flipboard and Calm, the Gmail account management team has reached out to test new features: I was able to use promotion cards and AMP for email as part of the Gmail beta programs. Is it an exclusive club? I don’t know. But it does feel kind of cool to test new features in the world’s most popular email service before most people.

In this case I think the kindly folks at Gmail came up with Promotion Cards annotation to give emails extra visibility on mobile clients to make up for banishing marketing emails into the Promotions tab. You can see a Promotion Card in action below.

As you can see above, Gmail added a bold “Promotions” section at the top of the Primary Inbox. That space contains a couple of teasers for the Promotions Tab (buybuy Baby, Carter’s, etc.).

Observations: increased open rate in 3 tests, decreased in 1. The case where promo code loss may be due to poor subject line choice.

Observation: less clicks

Observation: sales inconclusive.

Result: slight edge to promo cards but it will not change your business. Take it or leave it.

How to set up your email domains and SPF records

What is SPF (Sender Policy Framework)?

SPF is a DNS TXT entry for your domains and subdomains that list the services and individual IP addresses that you use to send emails.

v=spf1 include:_spf.google.com include:_something.amazonaws.com ~all

Hypothetical SPF record. This says that I use Google and AWS to send emails

SPF helps prevent email address spoofing because ISPs can look up the TXT record and compare with the email headers to verify that I acknowledge that I want Google or AWS to send emails for me.

Here is a larger SPF record. Note that in the block above I have 4 include: lines. That means I have 4 SPF records for my domain.

# infoentropy.com
v=spf1
include:_spf.google.com         # 1
include:u123456.wl.sendgrid.net # 2
include:other.service.com       # 3
include:other.service2.com      # 4
-all

Now, a problem: according to specificiations, each domain can have a maximum of 10 SPF records in each DNS TXT record. If you have more than 10 SPF records the ISP could ignore the entire DNS record or only look at the first 10 while ignoring the rest.

If I used my root domain for all email services, I would reach the 10-record limit quickly. Look at the table below — a medium-sized company could end up using many different SaaS platforms, each of which vies for space on the root domain.

Software serviceDepartmentwhat do they send?
GmailEveryoneall emails
MailchimpMarketingEmail blasts
Blog platform (WordPress, Squarespace, etc)MarketingBlog announcements
CRM (Salesforce, Hubspot, etc.)SalesCorrespondence with customers
e-commerce (Squarespace, Magento, etc.)SalesPurchase receipts
Customer Support (Zendesk, etc.)SupportHelp tickets
Surveys (SurveyMonkey, etc)MiscellaneousProduct survey, customer satisfaction survey, etc.
Transactional emails (Mailgun, Sendgrid, Sparkpost, AWS SES)EngineeringThings related to your apps
Engineering Internal Services (Jenkins, datadog, github)EngineeringStuff engineers look at
Legal things (DocuSign, etc)Legal
Finance (ADP, Carta, etc)Finance
Recruiting emailsHR
More stuff! JIRA, ASANA, Slack, BOX, DropboxEveryone
Various outbound emails & vendors that might use your domain name

This is 13 SPF records trying that would need SPF records. However, not all of these services necessarily need to be on the root infoentropy.com domain. I can have more than 10 SPF records by using multiple subdomains. Each subdomain can have 10 records.

Use multiple email subdomain names to stay under the SPF 10-record limit.

My proposed solution is to, loosely, divide my email domains according to business function: sales, customer support, marketing/bulk email and product, and internal.

Doing so will (1) give recipients have some clue of who is sending the email and (2) allow you to identify vendor deliverability issues. For shared SaaS services you might include that sender in more than one subdomain SPF record. SurveyMonkey, for example, might be used for more than one business function.

  • Sales: biz.infoentropy.com
    • reports@biz.infoentropy.com
    • Sales
      • hubspot
      • salesforce
      • squarespace
      • SurveyMonkey*
  • Help: help.infoentropy.com
    • support@help.infoentropy.com
    • Support
      • zendesk
    • Transactional (password reset, billing?)
      • AWS SES*
  • Marketing: email.infoentropy.com
    • deals@email.infoentropy.com
    • High volume bulk email
      • Iterable
      • Mailchimp
      • Pardot
      • Marketo
    • Surveys
      • SurveyMonkey*
  • Product: app.infoentropy.com
    • notifications@app.infoentropy.com
    • Transactional (you did something in the app!)
      • Sendgrid/Mailgun/AWS SES*
    • Notifications (X sent you a message)
      • Sendgrid/Mailgun/AWS SES*
  • Internal/corporate: corp.infoentropy.com
    • jeff@corp.infoentropy.com
    • Gmail/Outlook 365?

*Single service used on multiple subdomains.

In this situation I need 5 separate SPF TXT records, 1 for each domain. Each domain lists the specific services that I use to send emails.

# help.infoentropy.com
v=spf1
include: _spf.zendesk.com        # 1 Zendesk
include: _spf.amazonaws.com      # 2 AWS
-all

In this case I only use 2 services to send something@help.infoentropy.com emails. If I tried to send with the address jeff@help.infoentropy.com via Mailchimp, the verification would fail DMARC and the email would end up in the SPAM folder.