Problems 💥

The Penny Hoarder (TPH) had been sending out 5 different newsletters — 1 daily, others weekly or bi-monthly — to more than 450,000 subscribers, with affiliate and sponsored content playing a major role in revenue generation. But for several quarters there had been worrying trends:

📉 Steady decline in subscriptions and affiliate sponsorships

⬇️ Dwindling organic/paid conversions

☹️ Lower reader satisfaction (~37%)

🔺 Increased competition (FinanceBuzz)

As part of a larger initiative to re-brand The Penny Hoarder as PennyPlus, I led a content and product design team that proposed a new, more positive newsletter experience for readers — now called PennyPlus Daily — to reverse the slide.

Goals 🏆

User Goals

• Provide readers with more useful, helpful information ℹ️

• Give readers more reasons to keep subscribing 🗞️

• Reward readers with a more satisfying experience 😊

Business Goals

• Increase affiliate conversions by 25% ↗️

• Increase subscriptions by 10% 📈

• Attract a younger, more diverse audience 👧🏾👧🏻👧👧🏽

• Test proposed PennyPlus branding 🧪

Research Insights 💡

To identify problems with the existing TPH Daily newsletter, I created a survey with questions to discover readers’ satisfaction with the newsletter content and motivations for unsubscribing.

After surveying a total of 4,592 people and analyzing their responses, I discovered three main reasons for low satisfaction:

• Repetitive Content 🔁

• Not Enough Helpful Content 🛟

• Lack of Variety / Visual Interest 🎨

Other key insights 💡

• Variety 🍱 — 52% of participants said they want more diverse, engaging content, with ~25% of participants stating the content was “repetitive”/”repetitious”.

• Visuals 🖼️ — 76% said want videos and graphics

• Valuable help 🛟 — When answering the question "What are the most important factors when deciding whether or not to keep subscribing to a newsletter?" 88% answered "Helpful information" with 63% answering "Provides practical value for my time"

• Trust 🪟 — 93% said they want an open, honest, transparent relationship about advertisers

• Language options 🇲🇽🇨🇺🇬🇹🇩🇴🇵🇷 — 23% of young participants said they were bilingual or would appreciate Spanish-language content

Competitive Audit 🍎🍊

Today's personal finance marketplace features no shortage of newsletters. To best understand the competition space, we subscribed to more than a dozen of these newsletters during the latter half of 2022 to learn more about content and presentation.

We also performed a competitive analysis to see how they handled the key frustrations — repetitive content and a need for more helpful articles and visual interest — that users reported in my survey.

Below is a summary of how 3 of today's leaders in personal finance newsletters (Morning Brew, Finimize, and Finance Buzz) handle variety and visual interest:

• 15 newsletters

• 4M subscribers

• 4 podcasts

• $50M revenue as of 2022

Content Variety

• Longest and most varied of all newsletters

• Full articles, short paragraph items

• Bulleted lists

Visual Interest

• Mix of designed graphics, stock photos, animated gifs

• Emojis

Reasons to return

• Stock market summary at start

• Puzzles at end

• Calendar of events for week ahead

• Referral program

Key insights💡

• More diverse content — a mix of text, short lists, graphics, video

• All content is written primarily to inform, rather than sell or drive clicks, even sponsored content

• 850k+ subscribers, 🇺🇸 550k 🇪🇺 190k 🇬🇧 110k

• $1M revenue as of 2022

Content Variety

• Full articles

• Bulleted lists

Visual Interest

• Simple, designed graphics

• Scannable articles

• Charts/graphs

• Emojis

Reasons to return

• Upcoming events/news

• Analysis

Key insights💡

• Less varied than Morning Brew

• Informative articles

• Transparent about ads

5 newsletters, 1M+ subscribers

Content Variety

• Had least variety of all newsletters

• Most click-baity

Visual Interest

• No designed graphics

• Stock art like old TPH newsletter

Reasons to return

• Market summary (copy of Morning Brew)

Key insights💡

• Least varied of newsletters

• Least informative, heavily promoting click-through

• Annoying — readers are barraged by seemingly constant newsletter mailings

Content Insight💡

Across the dozen or so newsletters we analyzed, we noted a key trend that other newsletters employed and that TPH’s lacked:

🔥 Widespread use of Smart Brevity

Smart Brevity is an audience-first content formula created by Axios that states that modern readers scan — they don’t read — and so to be most effective all messaging should use:

• short, scannable chunks of text with bulleted lists

• punchy, meaningful writing that helps explain

• emojis and graphics to add visual diversity

User Personas

To better understand how to design for users seeking more variety or more visual content, we created user personas for each type of user, using information and data from our surveys and interviews.

Below is a brief version of Debra’s persona, a 67-year-old who lives in Central Florida, works two jobs, and is looking for ways to save money. Debra was used to understand the current, regular Daily newsletter reader who would care more about varied content than visuals.

User Persona (Debra)

Debra Mitchell

• 67-year-old woman

• Lives in Orlando, Florida

• Works at a Publix supermarket and as a DoorDash driver

• Annual salary ~ $65K

Use Case

• Living month-to-month

• Inflation really affects groceries, driving — she shops and drives less

• Saw ad on a Facebook post, clicked and went to article

• Signed up for newsletter on website

• Wants help in her working “retirement”

  🛟 Needs: practical, useful ideas to make and save money

  😡 Frustrations: the current newsletter keeps showing the same old bingo app “articles” that don’t help her; too many ads posing as “news”

Quote

“I have a lot of debt. I work 48 to 60 hours a week. . . but I’m not getting too far ahead. I need help!… I would like to see something besides playing bingo on your phone or switching car insurance.”
— Debra

To view the full version of Debra’s User Persona, including her motivations and frustrations, open the Notion project.

User Persona (Etty)

Etty was used to understand a younger, bilingual struggling student who would care more about learning through visuals and video tutorials — long paragraphs of text make her eyes glaze over — but still is looking for help and information to share with her abuelita.

⚠️ Debra was the dominant newsletter reader at the time; through the re-design we wanted more readers like Etty.

Etty Gutierrez

• 25-year-old, bi-racial woman who lives in Austin, Texas

• Bilingual, some older family members only speak Spanish

• Intern at Dell Technologies, makes $35k/year

Use Case

• Struggling with student debt, high cost of housing, inflation

• More interested in video tutorials to simplify financial matters

• Would like more bilingual/Spanish-language content to share with abuelos

🛟 Needs: simple, easy to understand, visual guides to managing money, side gigs, and investing

😡 Pains: Not going to read a long listicle of ads

Quote

“The site looks outdated and needs more video content. ”
— Etty

Content Strategy & Design

Shorter, scannable, more visual and engaging

The original goal of PennyPlus Daily was to develop an experience that readers would benefit from, enjoy, and return to on a daily basis.

What we realized early on was how this redesign would significantly involve a reassessment of our content strategy and design.

Fixing the interface wouldn’t fix the content we filled it with, and our readers (and competitors) were telling us to evolve and change.

As my background straddles both editorial and design, I led a cross-disciplinary group to develop a strategy quickly.

Our strategy embraced both content changes and design changes:

• The newsletter should be more diverse — create a flexible, modular system that mixes a variety of content and visuals

• Editorial content should be shorter, scannable, more helpful

• Make creating variety easier for writers and editors

• Stories should inform more, tease less — less clickbait

• At least 3 links should be visible above the fold in case readers don’t scroll

Early Iterations / Sketches

Creating a flexible, modular content system to create variety and conversions

We started by sketching a big-picture view of the newsletter to get a sense of how to create variety and rhythm.

And we started with mobile because analytics told us more than 85% of our users read on their phones.

Solutions

Above the fold

Our team sketched solutions to how we could increase conversion opportunities “above the fold” — the initial view by readers — in case they never scroll down.

• Currently, the number of conversion opportunities was, at best, 1

• We sought to (at least) triple this

Thematic Link Modules

Next, we sought to increase both visual diversity and helpfulness for viewers while providing more conversion opportunities. One solution was a series of regular and intermittent modules. Story links grouped by themes would be interspersed throughout the newsletter, alternating by day, week and season. The modules would:

• Build diversity into the structure by breaking up text

• Add coherence and flow to the newsletter by organizing links

• Create conversion opportunities

• Afford readers helpful information around a topic

Sponsored Content

One important aspect of the content strategy was creating a more editorial-friendly design for affiliate content. We created parameters for affiliate article including:

• Clearly marked as an ad

• Written more like helpful stories, rather than ads

• Designed to be engaging and informative

• Be short and scannable

• Have a prominent call to action button

In short — the sponsored content should better resemble PennyPlus content.

Weekly Infographics and Video

Unlike many of its newsletter competitors, TPH creates its own exclusive video and interactive graphic content, often quite practical and helpful. Just what our readers wanted.

But the current newsletter wasn’t leveraging these advantages. We wanted to give readers good reasons to keep subscribing by offering exclusive interactive graphics and video.

• Add a regular “Chart of the Week”-type section highlighting a topical interactive graphic, like national gas prices

• Add regular, entertaining videos focused on practical issues, like this review of gas station coffee

Wireframes

Putting it all together to test it

The wireframes for the new PennyPlus Daily focused on fleshing out the concepts we sketched earlier. A key concern was balancing user and business goals — increasing usefulness and conversion opportunities — while creating a structure that would help editors and writers more easily create newsletters that were interesting, helpful and reliable.

Design constraints

Due to the inherent cross-platform design constraints in email newsletters — basically, one can only reliably use system fonts like Arial and Comic Sans Times Roman — the wireframes we worked on in Whimsical turned out to be fairly close to the look and feel of the final product.

Header

Table of contents with links above the fold

Primary article

Show more of the story

Secondary articles

Vary for more visual diversity

Thematic link modules

Weekly, monthly, and seasonal

Sponsored content

It’s an ad, but helpful

Videos and infographics

Spice up the editorial mix

🧪 Early testing validates hypotheses

Before getting too married to our designs and concepts we tested our wireframes with a handful of “super users” from TPH’s Community online chatroom to determine whether we were on the right track.

Results validated our initial concept and user satisfaction jumped by 51% so we knew we were on the right track. And from the suggestions we got, we iterated changes to the design.

🧪 More testing with newsletter readers

Interactive prototype

From wireframes, I created mockups and an interactive, high-fidelity prototype in Figma designed for mobile to test with current TPH newsletter readers.

In our initial test, we ran an unmoderated session with 8 newsletter readers on Maze. Our questions were split between qualitative (satisfaction) and quantitative (conversions) metrics. Following our test, we iterated on the design and tested it with another group of readers.

🎉 Outcome

👏 Satisfaction more than doubles

Surveying readers after testing we found the number who were “very satisfied” with newsletter content doubled to 54%. Now more than three-quarters of respondents were “somewhat” or “very” satisfied with the design, up 30%.

Readers said they were enthusiastic about our new design:

“So much better! More realistic articles. . . Not the same thing over and over.“
—Angie P.

“Love this! Greatly appreciate the improved quality. The video is fun.“
—Andrew H.

📈 Triple the conversion opportunities

The new design provided triple the number of opportunities for readers to convert:

• ❌ The old newsletter design provided 8 links total, on average, with 0 above the fold on mobile

• ✅ the new design offered an average of 24 links total with at least 3 above the fold

🔥 Key Takeaways

🔊 Listen to our users — User research revealed many readers desired more practical, helpful information over uncritical advertising. By understanding readers we were able to focus on structural and content problems to address.

🏡 Give readers a home — Readers wanted practical information, and reasons to return to the newsletter. Providing more practical information in articles —— as well as visual content like graphics and video — gave readers a more engaging experience.

🧪 Early-stage testing — Before spending a lot of time on high-fidelity prototypes (much less development), quick testing with readers gave us the confidence to back up decisions with real data.

🛠️ Toolstack

• Figma — design

• FigJam — workshops/whiteboarding

• Whimsical — wireframing

• Balsamiq — sketching/wireframing

• Maze — unmoderated user-testing

• Google Slides — stakeholder presentation

• Slack — communication with users

• Zoom — communication

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