Well-intentioned product marketing suggestions from a software-loving, crossword-solving Will Shortz fanboy

Armchair Consulting is a series of articles where I make marketing suggestions for businesses I love. If you’re involved with the NYT Crossword app and you want to connect, contact me here.


Well-intentioned product marketing suggestions from a software-loving, crossword-solving Will Shortz fanboy

Armchair Consulting is a series of articles where I make marketing suggestions for businesses I love. If you’re involved with Here’s the Thing and you want to connect, contact me here.


My wife and I are NYT Crossword nuts.

We solve it together…

We analyze our stats together…

We laugh at all of the Brooklyn 99 references together…

While most hardcore puzzlers are pencil and paper purists, we play it exclusively on the app.

It’s a GREAT app, don’t get me wrong. But the growth marketer in me can’t help wonder why they haven’t developed features and campaigns that could take it from the fringes to the masses—especially during a time when most people are self-isolating and looking for games to fill the void after episodes of Ozark and Tiger King run out.

So here it is: my wishlist of top 10 features I think the NYT Crossword app is missing.

Me giving unsolicited advice to one of the greatest institutions in the world because I’m 28 days into self-isolation and bored out of my tree.

Top 10 changes I’d make to the NYT Crossword app

1. Better engagement with friends & family

The app’s ability to interact with friends is pretty much non-existent.

Done well, this could have an exponential effect on user acquisition—especially when everyone is social distancing and looking to connect remotely.

The Leaderboard does allow you to add connections, but it’s limited to the Mini and it only shows the current day’s standings. There’s no history, no scoreboard, and no view over time.

Imagine a Leaderboard that allows you to…

  • See standings for the full puzzle, not just the Mini
  • Compare weekly and monthly times in addition to daily times
  • View friends’ badges & accomplishments (more on this later)
  • Opt into a public leaderboard where you can connect with other crossworders in your community or around the world

In addition to a better Leaderboard, imagine messaging friends back and forth or adding people to challenges and taunting them along the way.

“Betcha can’t get the theme today!”

“27 down was a tricky mofo!”

“Tell me 18 across doesn’t remind you of Cynthia LOL!!!”

Here’s where cheering, taunting, and messaging live in Fitbit, for example. Easy peasy.

Commenting on clues or setting up competitions could be big, too. Think lifelines for people who want to “phone a friend” and better gameplay for working on puzzles together—aka a “loveseat mode”. For example, my wife is a flight attendant and it’d be great if we could collaborate while she’s away without having to leave the app.

Sky’s the limit. The more people engage inside the app instead of having to talk about it elsewhere—or worse, not talk about it at all—the more they’ll want to add others.

2. Easier invite functionality

Engaging with friends is great but useless if you can’t invite them in the first place.

The current app gives you a shareable link—not ideal. Invites should be integrated with your address book and social profiles. Again, check out Fitbit.

Notice how they say users with one friend are 27% more active than those without?

Make it e-a-s-y. Don’t force people to copy a link, scour their phone for friends, and come up with an invite message on their own. Let them tap a button and customize a line or two, then BAM! they’re off to the races.

3. Improved statistics & coaching

The stats in the Crossword app are as disappointing as the ending to Game of Thrones.

All you can see is total number of puzzles solved, solve rate, current streak, and longest streak, as well as daily, weekly, and total averages.

I’m no quant, but there have to be better metrics to share. People want to know if they’re improving, compete with themselves, and learn about their habits.

Here’s what I’d think about adding:

  • Completion rate. Instead of only showing how long it took to complete a puzzle, show what percent of puzzles were correct before having to check or reveal. That’s a more sensitive indicator than “solve rate” to see if you’re improving.
  • Frequently missed words. If there are words you keep getting wrong (“UMA”, “ELLA”, “REDSOX”), wouldn’t it be nice to know?
  • Novelty metrics. Add amusing metrics like “Hunch Rate” (what % of words or letters you enter correctly on the first try), “Power Hour” (the time of day you complete puzzles fastest vs. slowest), or “Category Breakdown” (topic-specific insights, such as “You solve 82% of entertainment-related clues correctly but only 44% of sports clues correctly”). Even though they’re only for shits and giggles, they’ll add a ton of delight.
  • Brute-force factor. “Brute forcing” is when you get to the end of a puzzle and there’s only one square left so you rapidly punch in letters until the “Congratulations!” message pops up and delivers your daily dopamine rush. Is it cheating? Questionable. Regardless, hardcore enthusiasts want to know when they’ve actually won versus hacking a square.
  • Solve threshold. The solve threshold is the percentage of a grid where, if reached, someone would be able to complete the rest of the puzzle. It’s tough to quantify, as it would need to take into account puzzle-by-puzzle variance, but a bit of machine learning could do the trick.

Why is it important to add stats like completion rate and missed words?

Max Deutsch’s article How I mastered the Saturday NYT crossword puzzle in 31 days illustrates why improving the app’s metrics is key, particularly for beginners.

“On July 1, 2017 I was able to successfully fill in 30% of the squares in the Saturday puzzle, which was better than I expected. After training for a week, I tried to complete the July 8, 2017 Saturday NYT puzzle…and successfully filled in 47% of the squares—a nice improvement of ~57%.”

Deutsch credits his success to three activities:

1. The Crossword Trainer. Using his home-built Crossword Trainer, Deutsch memorized 6,000 pairs of the most popular crossword clues.

2. The Letter Trainer. Deutsch used the Letter Trainer twice a day as a 15-minute warm-up activity. In total, he spent 3.5 hours on this before being able to solve a Saturday puzzle.

3. NYT practice puzzles. In one month, Deutsch completed 62 NYT crosswords. Most of these puzzles were Saturdays, but there were also a handful of Fridays and a few puzzles from earlier in the week.

Most people aren’t as structured as Deutsch in their learning approach, so why not give them a coach? By incorporating better metrics and maybe even a crossword trainer into the app, you encourage improvement and attract more beginners to the platform.

Yes, some may see a “crossword coach” as taking the fun out of it, but what fun is peaking at the Wednesday or Thursday puzzle and never getting any further?

4. Constructor mode

Every Christmas, I renew my wife’s subscription to the Crossword app and make her a homemade puzzle featuring clues of things that happened to us over the last year.

I know, barf. But get this…

Currently, I have to use programs like Crossword Hobbyist to create puzzles.

One of the many sites I’ve used to make crosswords, which of course requires a credit card for a free trial that I inevitably forget to cancel and wind up spending $50 on before begging a customer service agent to get it back.

How great would it be if people could make their own grids to share with friends?

This is where NYT should think BIG.

Super Mario Maker is a great analog. It’s Nintendo’s best-selling franchise that allows fans to create their own courses based on the Mario universe, share them online, and play levels designed by other players.

Maybe it’s a pipedream (Mario pun intended), but why couldn’t NYT do the same?

Whether they build the tech themselves, license their brand, or integrate with other platforms that already exist, it’s a smart move to diversify formats and channels.

What this really comes down to is adapting the brand to evolving consumer behavior. The next generation of puzzlers—both those who already dig crosswords and those who don’t know it yet—enjoy massive multiplayer games and customizable experiences. If NYT doesn’t capitalize on these opportunities, another publisher will. That’s how disruption happens. (Read Clay Christensen’s The Innovator’s Dilemma.)

No one denies that the Times has the best puzzle in the world…for now.

But if they don’t expand platforms and functionality, it won’t be long before the competition does and people start thinking of WSJ or The Guardian or even Nintendo first when it comes to crosswords, and that would be a devastating blow to the brand.

5. Badges & achievements

It’s no secret that achievements are crucial for game psychology, so why does NYT ignore them outside of the gold squares you get when you solve puzzles without help?

USA Today’s crossword gives you badges for holidays, streaks, qualifying in tourneys, evening play, and more. How awesome is that!

Out of all my suggestions, this is the easiest and least controversial to implement.

NYT’s team should take 60 minutes to think up creative badge ideas and get them into a developer’s backlog. It would add a whole new level of delight to the experience.

A few ideas to get started…

  • Beginner badges: every day of the week, no hints, successful rebus, etc.
  • Badge for 2+ day streaks up to a month
  • 1, 2, 3…12 month streak badges
  • Time badges for solving in certain timeframes
  • Holiday badges
  • Theme-specific badges you can only earn by solving on specific days
  • Tournament badges for participating and ranking in different competitions

By adding badges, you challenge your fans and encourage new players with positive reinforcement. That’s important as you expand the audience beyond the traditional Times participant, especially if there’s an influx of new users during COVID-19.

6. Unlimited free tier as long as the pandemic lasts

NYT should offer the Crossword app for free as long as the COVID-19 pandemic lasts.

Beyond being a good acquisition move, it’s the right thing to do—especially since New York is the hardest-hit city in the world right now. It’s a perfect time to say “The only thing tougher than our city’s crossword is our spirit. We’ll get through this, New York. In the meantime, here’s a gift to make staying at home a little easier.”

Alternatively, they could donate the proceeds to fighting Coronavirus in NYC. Anything to get the message across that they’re New York Strong.

Acquisition-wise, the benefit of course is that the Crossword is so addictive most people who try it during the pandemic will turn into long-term subscribers. It’s got a short “time-to-wow” and early “aha moments”—everything the Reforge model extols.

Ahh, the joys of marketing a product people love.

7. Influencer campaigns

Sometimes the best remedy for a bad situation is a dose of humor.

Wordplay, the 2006 documentary about the American Crossword Puzzle Tournament (ACPT), highlights how funny, positive, and tight knit the crossword community is. It also shows how popular the puzzles are amongst the likes of Jon Stewart, Bill Clinton, Bob Dole, Ken Burns, and other well-known figures.

It’s easy to imagine a campaign featuring comedians and other celebrities, both real and fictional, who love the crossword.

Andre Braugher’s character on Brooklyn 99, Raymond Holt, would be a great face for a crossword campaign. Perhaps weave in Melissa Fumero’s character Santiago for a competition between the two?

This is when endorsements work magic—when the product is tied to the influencer’s brand. Alternately, you could go down the grass-roots path and get a handful of celebs to challenge each other while self-isolating. Or you could feature them on a dedicated blog or video series, similar to Wealthsimple’s Money Diaries.

Any way you look at it, influencers are a great opportunity given the fact so many of them are proud New Yorkers and love the crossword already.

8. Delight the most active users

True story: a colleague of mine met Will Shortz a few months ago and, remembering my wife is a huge fan, recorded a video of him inviting her to play table tennis in Westchester.

Here’s the clip…

Crossword fans would crap their pants and tell everybody they knew if they got this.

That’s because nothing is better for word of mouth than delighting your fans.

The best part? It took Will 10 seconds to record that video. I’m sure he’d be able to pump out a ton of them if his team shared a list of randomly selected superfans every month. Yes, it would take a little effort, but in many ways the best marketing is unscalable.

Alternately, you could scale this idea by recording a generic message from Will and personalizing it with text. Think Facebook Memories. Even automated congratulations or pats on the back would work.

Aside from relying on Mr. Shortz, you could:

  • Send appreciation or holiday cards by mail or email
  • Get other crossword personalities (constructors, tournament winners, etc.) to record messages and share with superfans
  • Mail crossword merch to select winners—e.g., mugs, calendars, shirts, etc.
  • Give away a trip to New York to tour the Times and meet the crossword crew (post-pandemic, of course)
  • Choose a winner and mail them an iPad with a New York Times case since the Crossword app is so much better on a tablet than a phone or computer
  • Give away free Crossword subscriptions to randomly selected superfans who solved the puzzle every day in 2020

Going above and beyond with superfans is always a good idea. The community will love it, and it’ll encourage people to play more to unlock surprise rewards for themselves.

Moral of the story: anyone who plays the crossword religiously should be rewarded in the form of surprise videos, bonus content, special badges, and more.

9. Analytics-driven marketing campaigns

With so much data at the Times’ fingertips, I’d use it to get creative with geographic campaigns—especially on social media where ad costs have dropped during COVID.

For example, Spotify’s ad campaigns are top notch. Check out their clever billboards.

Instead of billboards, I’d do display ads and social campaigns.

The possibilities are endless. Here are some examples with an NYT twist:

  • “To the 3,441 New Yorkers who stayed up until 3am solving crosswords last night, you give this city its reputation. Never change.”
  • “Be as loving as the 612 people in Rome who said the answer to ‘Inspiration’ on Sunday’s crossword was ‘Mom’”
  • “To the person who thought a six-letter word for ‘Disappointment’ was ‘Darryl’, what did he do to you?”
  • “For the 14 people in Lansing, Michigan with the NYT Crossword app, two questions: 1) Do you also have a book club, and 2) Can we join?”

10. Document, Don’t Create

The last suggestion on this list is the one I’m most passionate about, purely because I’ve seen it work at all types and sizes of companies.

It’s called Document, Don’t Create. The idea is simple: successful marketing strategies are built around publishing a lot of content on a regular basis, and the only way to do that scalably is by documenting your process and repurposing it.

Specifically, I think the Times should hire a videographer whose full-time job it is to document the process of creating, editing, and publishing the daily crossword.

This may be difficult while everyone’s remote, but you’d be surprised how much there is to capture from Zoom interviews, going Live on Facebook, and more.

Once the content is captured, it should be repurposed into articles, podcasts, and vlogs.

This approach works for a lot of reasons—mainly the following.

Reason 1: Authenticity. People want raw, uncut conversations and behind-the-scenes content more than anything else—especially during difficult times. When you throw out the scripts and start sharing authentic moments, things start to take off.

Reason 2: It allows you to pump out content. Fast. When it comes to producing content from scratch vs. documenting your process and repurposing footage, there’s no contest. One documented clip can turn into 10 social posts, 2 blogs, 5 YouTube clips, etc. Yes, you still need a content team, but they’ll be focused on coordinating and repurposing material instead of developing content from thin air.

This is exactly why Wordplay is popular. The documentary highlights the people behind the Crossword and makes it more about the community than the puzzle.

How does Document, Don’t Create work? Simple. You hire someone creative and get them to start capturing. Tell them to follow Gary Vaynerchuk’s content model and you’ll see stellar material in no time.

In Summary

The NYT Crossword is the world’s best puzzle in the palm of your hand, and with a few improvements, the app and its marketing could match the quality of its superior content.

If I held the reins during these difficult times, I’d focus on:

  1. Better engagement with friends & family
  2. Easier invite functionality
  3. Improved statistics & coaching
  4. Constructor mode
  5. Badges & achievements
  6. Unlimited free tier as long as the pandemic lasts
  7. Influencer campaigns
  8. Delight the most active users
  9. Analytics-driven marketing campaigns
  10. Document, Don’t Create

At the end of the day, there’s no reason the NYT Crossword app shouldn’t be one of the top games in the Appstore alongside Bingo Blitz, Scribblenauts, and others. Everyone I introduce it to gets hooked in no time. They’ve just never considered it before.

And to anyone at the Times who stumbles across this post: leapin’ lizards! I hope I didn’t come across whiny or overcritical. You build one of my favorite products in the world, and I can’t thank you enough. Stay healthy, stay safe.

Are you from The New York Times?

Jiminy Cricket! If you’re interested in digging deeper into any of these ideas, I’m happy to hop on a call and discuss. Contact me directly at devonhennig@gmail.com.


About the Author

Devon Hennig is a software-loving, crossword-solving Will Shortz fanboy with 10+ years experience in digital marketing. He is currently VP of Demand Generation at Vendasta, a 400-person software company that provides marketing solutions to agencies and media companies, including Hearst, iHeart, McClatchy, BH Media, and 2,000+ others.