When the CEO read about journey mapping in Harvard Business Review, I was asked to analyze and redesign one of the most complex and frustrating efforts in the customer experience - in-store checkout. Leveraging my film background, I ran an unconventional approach to journey mapping by filming checkout like a reality TV series.


Journey Mapping: What’s It For?

This case is a detailed deep dive into a section of the bigger (MaaS) Macy’s as a Service Case Study.

  • A request from the CEO in the summer 2016, after reading an HBR article about the value of journey mapping.

In an interview with the Robin Report, Macy’s CEO Jeff Gennette says:

  • “End-to-end customer journey mapping is the new frontier for all of us and the answers are not monolithic...”

  • “So, a balanced strategy is required for a department store moving forward: address the needs of your core customer while adapting your goods, services, and touch points for your future ones.”

Image of sketchbook and patches.
Macy’s checkout journey map. All processes and breakdowns are listed in sequence from left to right.

A journey map is a visual representation of the customer experience that a user goes through to achieve a specific goal.

  • You get a clear evidence based sense of your customer motivations, their unmet needs, and pain points.

  • With the data collected, you have a clear idea on what to improve for the next design of the customer experience.

Image of three resonant waves.
An old IBM Point of Sale system that is about to be replaced.

The in-store infrastructure (point of sale systems and associated handhelds used to scan inventory) were coming to an end of lifecycle transition.

  • With the prolific use of mobile devices, combined with the ascent of all payments eventually going digital - this was a unique opportunity to redesign an omnichannel shopping experience.

  • This also provided a great opportunity to gather new data reflecting changes in customer behavior, that could feed AI/ML models for future trend analysis and merchandise forecasting.


In-store checkout captured all the company wide dilemmas, and no one wanted to publicly acknowledge them for fear of punishment.

Image of sketchbook and patches.
In store checkout functioned as a customer service catch all and thus add time to the process for all shoppers.
  • There was a massive disconnect between what was happening on the ground, and what the C-Suite actually saw.

  • Second, Macy’s was about to change CEOs, which provoked the middle management chain to become even more averse to change.

  • The question was, how do you capture and present the truth without agitating anyone, while also communicating a complex situation simply?


Although I operated as a change management consultant, I started as UX Architect, and grew into an unofficial Chief of Staff to the VP of Customer Experience.

  • I started by redesigning the dot-com vision, and that grew into the complete redesign of corporate vision.

  • This journey map operation emerged as an extension of that UX strategy work - because I had a film background and network of collaborators, we could be flexible and adapt to changing circumstances.


I facilitated two in-person journey map sessions and it quickly became clear that communicating the true complexity of checkout was going to be difficult.

Quick 30 second clip highlighting a major pain point: not being able to break apart a gift receipt into multiple single receipts unless you return and repurchase the entire order.
  • During one of the data gathering/work sessions, someone in the middle management stack made a remark about hanging a few GoPros to film so the C-Suite could really see what was going on.

I have a film and sound design background, so I assembled a three person crew, hung four go pros - produced, directed, and shot it reality tv style with double system sound.

  • The strategy was to put humans (real customers) at center and show the challenges, rather than telling about it in presentations and slide decks.

The film was shown to the board, and because they were able to see the real customer pain, immediate changes were implemented:

  • A single place to check versus multiple empty registers scattered throughout the store.

  • A real understanding of the importance of data, and how an aging product catalog was hindering real growth within the company.

  • Finally a clear understanding of the knock on effects, and how each component failure cascaded to impact different parts of the company.

Macy’s CEO Jeff Genette talking about customer experience improvements while taping at Woodbridge, NJ (CNBC link).

Improvements were so successful, that the Woodbridge store (one of the journey map sites) was mentioned on an earnings call and other media appearances along with checkout improvement, signaling future changes to be implemented in the company.

  • Last, the operation was so successful that I was asked to journey map the call center operations for the company.

  • That research fed back into the wider MaaS strategy by feeding speech to text to our data models, to improve selection, forecasting, and customer loyalty.

  • The unconventional methods for journey mapping clearly supported my hypothesis for simplicity, convenience, and trust flywheel. The process was way too long, and by simplifying everything we could not only increase sales, but improve the omnichannel customer experience as a whole.


Two Locations

I ran two journey map sessions, one in Woodbridge NJ, and Oakridge in San Jose CA.

  • The first session was in a higher end store in the Westfield Oakridge Mall in San Jose.

  • The second journey map session was run in a smaller mall store in Woodbridge NJ, where we also shot the film.

Journey map sessions were run in two locations: Oakridge in San Jose CA, and Woodbridge NJ.

Each facilitation session ran about six hours, each with store associates and the VP General Manager for the store helping map out the entire process with post it notes.

  • Journey maps move linearly from left to right illustrating sequence, and top to bottom mapping out breakdowns and customer touch points along the way.

  • By the end of each process, you get a clear sense of what a customer has to endure, what is malfunctioning for the journey, and how the customer feels along each step of the way.

Facilitation session in Oakridge CA. All the associates helped and placed Post-Its along the path of purchase.

Cross Organization Collaboration

The two Journey map sessions was part of a larger collaboration with other stakeholders throughout the org:

  • Associates & Store Manager

  • Store Operations

  • Marketing and Loyalty

  • MST (Macy’s Systems & Technology) the unseen IT infrastructure

  • The wider Macy’s Inc Strategy

  • Credit (accounted for 40% of EBIT on our balance sheet)

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Slide outlining key goals set up for team collaboration between all the different stakeholders.

We triangulated data from other research initiatives:

  • Marketing research (providing quantitative data on customer need)

  • Competitive benchmark study (Macy’s Vs competitors)

  • UX historical research (qualitative customer needs)

  • Business requirements and valuation of programs

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Competitive heat map outlining all the extra steps customers have to endure during Macy’s checkout.

A Complex Process Begins To Emerge

Image of sketchbook and patches.
Image of sketchbook and patches.
Journey maps of Oakridge (left) and Woodbridge (right).

The two Journey map sessions was part of a larger collaboration with other stakeholders throughout the org:

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In store checkout takes 30 step to complete.
  • Checkout took 30 steps to complete from beginning to end.

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There were more than twice as many negative points than there were positives.
  • There were 17 points of positive sentiment, and 35 points of negative sentiment.

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There were 90 points of friction (broken pieces of the overall process) in checkout.
  • There were 90 points of friction.

The two Journey map sessions was part of a larger collaboration with other stakeholders throughout the org:

  • One of those people was my boss’s boss, and after seeing and hearing the complexity unfold in real time, he asked if we could hang a couple GoPros and film it.

  • This random serendipitous idea birthed a new creative method to run journey maps, which ultimately led to change throughout the entire organization.

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Prepping a multi-camera shoot for a separate client with GoPros. The gear selection was intended to be tactical in nature: i.e. be redundant, portable, and fast to set up and break down.



Preproduction involved aligning multiple ducks in a limited amount of time. Our goal was to film in as many FOBs (families of business) get as diverse coverage as possible.

Testing the Tentacle Sync system with a timecode slate.
  • We ran four Go-Pros with a Tentacle-Sync double system sound.

Picking up a bunch of gear from B&H.
  • I only had about 30% of what I needed, so I bought a bunch of gear at B&H - and ended up returning a bunch too lol.

  • I had to buy a handful of $25 gift cards, get release forms, run a few tech setups to make sure the Jam Synch worked.

Image of sketchbook and patches.
Image of sketchbook and patches.
GoPro has an iPhone app that gives you near real time feedback so you can compose your shots with confidence.
  • Last, it was off to New Jersey to location scout and run a few Camera tests.


Production day was long but a lot of fun.

  • We ran a three person tactical unit like a special forces style crew, carrying only four tactical packs (light and fast).

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Everything we needed to film fit into four tactical packs.
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Everything for the shoot fit onto a small mobile cart.
  • Each shooting location inside Macy’s Woodbridge had a four camera Setup: two main angles (left and right), a gimbal for a cinematic handheld feel, and finally a shot of the PoS (register) to get details on the customer and what they purchased.

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Four camera multi-camera setup sync with external wireless sound.


Editing was difficult and rife with challenges. We shot multiple cameras in 4K with double system sound.

  • The sound didn’t sync on two of the cameras, so we had to do it manually.

  • Other marketing groups wanted to edit the video so we had to move fast (less than a week).

  • Mercury retrograde was in full swing, and both my and the other editor’s computers were having lots of issues.

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Adobe Premiere kept crashing and producing weird errors during editing. This was the third new MacBook from Apple.

The good news was that we filmed so much good data, that you could identify all the company wide dilemmas (CX pain points) from this video (all the major paint points were evident).

  • Everything pointed back to our company wide dilemmas, but really echoed the fact that we needed to fix our tech foundations.

  • One sequence in particular caught everything we needed, so we made a judgment call to have the C-Level sit and watch the full 15 mins of pain. This way they would feel what the customers felt.


Four Main Pain Points

After running both journey map operations and filming in Woodbridge, four main areas of pain began to emerge.

  • Product Search: Not everything online or in-store was visible in the product catalog. Many items from Backstage lacked product tags (price tags), and items that customers wanted to see in different colors could not be located.

  • The Grand Bargain: The heavy reliance of coupons, discounts, and promotions trained customers to wait for sales - then question whether they were receiving the best bargain price. This added significant time to other shoppers waiting in line behind the current customer.

  • Persistent Prompting: Multiple marketing and credit prompts that front loaded the checkout flow making the process more complex and time consuming.

  • Customer Service Catch-All: Bill payment, returns, and price checking (all of which were separate from checkout) were performed or interrupted the checkout process and added significant time to other shoppers waiting in line.

Customer Experience Flywheel

We ran this complex flow through my UX Flywheel: Simplicity, Convenience, and Trust.

  • The challenge was balancing simplicity with necessity, while removing as much complexity as possible.

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The user experience flywheel that all journeys were analyzed against.
  • Simplicity: remove as much friction as possible. Make tasks one click, one tap, or one swipe to complete the action.

  • Convenience: Improve my length of quality of life, or give me my time back.

  • Trust: Be consistent, consensual, honest, and a good steward with my data.

Four Simple Steps

In order to simplify checkout from 30 steps, we reduced the process down to four and consolidated all the sub flows.

Image of three resonant waves.
Checkout was simplified into four simple steps.
  • Identify the Customer: The wider vision was about making every experience contribute to making the brand smarter as a whole, like how each Google search makes google a little bit better. Therefore we wanted to get customers identified, then pay them for their data.

  • Scan Merchandise: Get right to the point, scan your items and get them into the system.

  • Present the Best Deal: Make it very clear that we are providing the best deal to our customers, and if possible make it simple to upsell. We moved all the marketing prompts that used to front load the process here, all while leading with a value proposition that yielded the best deal.

  • Pay for Purchase: Introduce mobile payment options, while making order retrieval easy in case a customer wants to return an item later. This was also a place where we could have a concierge style service to hold merchandise for customers, so they could continue to shop, thus keeping them in store longer.


Troubleshooting The Output

The main boardroom in Herald Square is as old as the building itself dating back to 1902. Some of the old projector tech still remains intact - almost like a museum.

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The old projector tech was still located in the tech closet behind the boardroom.
  • I had to troubleshoot the output with the satellite team, because the San Francisco dot-com team was going to a video conference in San Francisco, while I played the video locally from New York.

Image of sketchbook and patches.
Image of sketchbook and patches.
Troubleshooting the projection system with the satellite team.
  • There was a video scaler issue, but we ruled everything else out to pin that down.

Middle Management Maze

On top of the technical issues, there was a lot of internal tension preparing for the big show.

  • I had to run multiple iterations of deck reviews because there was a panacea of middle managers across multiple divergent teams across the organization, each with competing interests and no one wanted to be blamed in case the C-Suite was displeased.

  • Second, there was a new CEO taking the reins (Jeff Gennette), hence no one wanted to be held accountable (most were let go within one to two years). Macy’s closing SF link.

  • Our main stakeholder was the then current COO, who was likely seeking to become the next president of the company (second in command to the CEO) who also was replaced within two years.

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View from the back of the boardroom before D-Day.

The Main Event

The final presentation went off without a hitch. The video looked great, and the management team really empathized with what they saw on video.

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View of the film playing at full fidelity the day before the big presentation.
  • It was clear on the film that no one could deny that some things really needed to change.

  • The C-Suite Made Changes because they couldn't ignore the pain.

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Opening still from the film.

We presented four vignettes as visual slides rather than making wireframes and designed comps, because managers typically got caught up in details, rather than focusing on the big pictures. Some highlights below include:

  • Present the Best Deal

  • Multiple Ways to Pay (including legacy systems)

  • Page a Runner and Hold Your Stuff

  • Fast Pick Up and Return

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Slide from Presenting the Best Deal Vignette.


Stock Price Soars

The journey map operation was part of a bigger redesign of the corporate strategy. When the CEO messaged a piece of our strategy, and mentioned Woodbridge as progress - the stock rose by $10 or $3B in market cap.

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When the CEO messaged out work on the earnings call, the stock rose $10 equating to a $3B in market cap increase.

Immediate Tangible Outcomes

Filming Journey Maps is an extremely effective tool when you need to persuade management teams.

  • Tangible Maps are still necessary to mark up and get into the details about the process, but to tell the story - there’s nothing like a short film to produce tangible outcomes.

Some select highlights that resulted from the Journey Map operation include:

  • Customer service centers were centralized into one location in every store.

  • A single place to check out from rather than trying to find the one PoS system that was manned inside the store.

  • A real understanding of data importance and how an aging product catalog was hindering real progress within the company.

  • Last clear understanding of company wide customer frustration pain points.

A surprise insight for us was that you could make Macy’s experiences fun like a casino by utilizing PoS in new and innovative ways. This supported one of the vignettes from our strategy pitch, positing that in store shopping is like a future playground - ie make shopping fun again.

  • This operation clearly supported my hypothesis for simplicity, convenience, and trust flywheel. Checkout was way too long, and by simplifying everything we could increase sales.

Call Center Operations

The Checkout Journey Map operation was so successful that I was asked to evaluate the call center in Ohio.

Image of sketchbook and patches.
Macy’s customer service contact flow.
  • The call center was even more complex because it was essentially a non-linear process.

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Shadowing live calls was super enlightening to understand what both customers and customer service employees experienced.
  • There was no one single journey that a customer could call in with, therefore it was more difficult to map out.

  • With that said, we discovered another missing link but ended up being an opportunity by taking speech to text and feeding that into our AI/ML models to improve the customer experience for everyone, when anyone interacted with the brand.

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The old customer service interface was outdated and antiquated.


I gave a presentation with Cameron Craig in the Social Engineering Village at DEFCON in Las Vegas in 2017.

  • The talk centered on how to change intractable corporate culture, and used our MaaS model for Macy’s as a case study.

  • How this impacted the wider corporate goals earnings call and stock jumping. Outlined in MaaS case.

Talk at DEFCON with Cameron Craig where we spoke about how to change corporate culture using Macy’s as a case study. Talk at DEFCON 26 on Youtube.