Prologue
Our Problem
Project Kickoff
Our Discovery
Our Solution
Stepping Back
More Findings
Retrospective
Epilogue
Our Process
During the build, it was exciting to see the team grow like a true startup. To sustain the expansion, our product team had to be adaptable as Entr was landing bigger accounts and pitching the product on stages like Y Combinator.

In April 2018, we launched an early beta for Entr’s TV appearance on Dragon’s Den. The full product launched later in August.
The launch
The rebuild helped Entr capitalise on their growth as they were advancing to new markets and growing their user base. Following launch, the app saw significant growth in terms of sales, user retention and conversion.
The results
  Entr raised a seed round of $1.13M from world class investors and VCs
✓  Internal team at Entr grew by 4x
✓  Signed major accounts like l’Oreal, Michael Kors & Bank of Montreal
We had clues from our studies on what the listing page lacked but it was still fuzzy. To have a grasp of the organiser thought process, I ran a small think-aloud exercise with 5 participants that focused solely on the listing page. My aim was to use these findings to redesign the listing page and its parent — the search page.

The study revealed that our participants were mostly struggling to find information that was already there. Questions like “Is the space capacity large enough for my event?” and “Is there a minimum of hours for a rental?” could all technically be answered but required more thinking than it should.

Going forward, I explored ways to rearrange existing information to reduce the time needed by Organisers when going through a listing.
Give the right information and only the right information
When looking at Entr’s current value proposition, it was currently skewed in favour of Organisers. The core product was not doing much for venue owners and it had been felt through out our early studies. I was confident that being mindful of both sides of the marketplace was going to trickle-down positively in the overall product experience.
Turning data into new features
The chat was integrated into the product, but did not have much perceived added value for Hosts. It was a must-have feature, but not one that delighted our users. In order to save time, minimise mistakes and induce more sales, I worked on a quote flow tackling the most time consuming activity for Hosts — closing a sale.
Less focus on the chat, more on the event
Going forward with design, two questions informed my strategy:

1. How do we induce better, faster and easier venue bookings?

2. How can we improve the value proposition for everyone?

Early on, it was important to leverage our discoveries. The first area I set out to rethink was the first steps for every event planner — choosing the right venue.
Better event creation for everyone
Entr makes sure that you always know what you are paying for, regardless of the amount of changes when negotiating. Review and pay online when ready, having the peace of mind that what you see is what you get.
No surprises when taking out your wallet
Entr saves you time by telling you early on what you can do and what to expect. After choosing a space, give us your schedule and attendees and we’ll instantly get you an initial quote.

At Entr, you can message venue owners with confidence knowing that you are both on the same page from the start.
We are your booking assistant
Entr is more than an app, it’s a group of event experts that know the complexity of creating great events. We are here to inspire and give you confidence that Entr is the right tool for the job. We cannot wait to see what you’ll do with our spaces.
New product, new identity
Entr is here to help your next event be a success. Explore exclusive event spaces and get to know the important details before any commitment.

Entr helps you secure the best deal and ensures peace of mind so you can focus on delivering the best event.
Rebuild of the core Entr app
A significant portion of our Hosts did not see Entr as more than a lead generator. Because Hosts felt like the app was basically a matching system, they were inclined to work outside of the platform and expressed behaviour that could corrupt some of Entr’s most active Organisers.

We asked ourselves the simplest question, how could we help users organise and host events in a better way? Our proposal was the complete redesign of their core product.
Unclear value proposition caused app-wide issues
Entr observed that venue browsing had a special role for Organisers. A coveted location, beautiful mezzanine or magical entrance were all features that sparked ideas and made events real for Organisers.
Venues are truly important
Organisers are the ones initialising conversations with Hosts and currently had the most incentives to complete their booking. Data revealed that Hosts were often slow in their replies and forced Organisers to look outside of their top venue options or the platform altogether.
Hosts are missing out on sales
The chat page was the leading drop-off point for our conversion flow. Hosts who did not feel like they were receiving enough value would encourage the other party to leave the platform and bypass Entr’s fee structure.
Loss of clients
Acquiring new venues is a driving KPI for Entr as a complete catalogue played an important role in their marketing strategy. Entr did not currently have the resources to go to venues themselves for registration and had to call or email venues — which seemed to annoy most vendors as it was a time investment with no guaranteed return.
Signing up new venues is crucial
Our initial study sparked clues and ideas but I now set out to understand the specific event planning reality shared by all of our users and prospects.

Since I was working with a team that had a real passion to help create great events and grow their vendors’ businesses, the founders were keeping close relationships with many of their Hosts and Organisers.

I partnered with the technical founder to gather the quantitative and qualitative data that the team had collected up to now. My aim was to gain a better understanding of the hopes and struggles of our users that had been documented by the team.
Understanding the event planning space
From the small study, it seemed like there was an issue beneath the scope of features. Thinking holistically, the heart and soul of the firm was event planning but the app did not follow through — it was a venue booking tool.

As I thought I discovered an opportunity to involve any and all event related vendors — diving into Entr’s non-digital activities showed that the team was far from leaving that money on the table. Entr had been manually upselling Organisers with catering and audiovisual services since inception.

With data to back up my assumption, I was ready to scrap our Airbnb style flow entirely and design based on events being planned from idea to completion and beyond. Although my hypothesis resonated with the founders, it meant drastic changes for the firm and ultimately for them, did not feel like a necessary thing to do at the time.

Instead of focusing on what we could do, we turned to the original plan for the core product rebuild — making an awesome tool that fostered great events.
UX is not aligned with business strategy
At the start of the project, we focused on getting a grasp of the health of the current experience for Hosts and Organisers. Since a vast majority of Entr’s users were professionals who used the tool daily and had found their own ways around the product, my aim was to generate insight that was inclusive of current but also new users.

When planning the study, I set out to test the app with 6 participants who had little to no prior knowledge of the platform. Organisers were tasked to book a listing and Hosts to close an incoming lead — both were given user scenarios to guide their experience.
Early investigation
When talking about the app, organisers felt that they were booking a venue rather than planning their event.
Wrong user mindset
Hosts had to repeat much of the same information from conversation to conversation and had to search through chat rooms when preparing a quote (e.g. dates and start/end times).
Inefficient lead process
Since payments were handled manually outside of the platform, it was hard for Hosts and Organisers to feel secure about their booking.
Cheques and phone calls
When Hosts were tasked with closing their lead, all they could do was chat. No negotiation process was in place and extra files had to be sent over email.
Unassisted negotiation
The listing feed was frustrating Organisers during their search. Loading images felt too long (especially on mobile) and created confusion as UI elements were blank (i.e. no lazy loading).
Performance issue
Less than a year later, Entr pivoted to an event-based flow instead of a venue-based approach that was mandated for the rebuild. This could be a case of we told you so but I believe it stems from the general perception of design.
Hierarchies are real
It seems like we have a natural tendency to value design when solving a problem but much less when defining it. We had a hunch, a bit of data but did not fight strongly enough for the pivot. All is well now but I still believe an earlier shift would of been a better move for the product.

With clever founders, I reckon this realisation will induce a strong shift into user centric practices everywhere in the firm. Cheers to seeing the team become a unicorn!
Halfway through the build, the founders managed to score a spot on TV to pitch and promote their product — which would be aired in a few weeks.

We managed to put out a decent beta in time for the show. Under the hood though, code review and commenting had lacked and we knew refactoring tickets were creeping on us.

Although the impact from the appearance is hard to measure, it definitely had a great impact in terms of marketing, exposure and credibility. From a product perspective though, the rush had created a few surprises for the rest of our build.

Not crashing during the expected surge in traffic was a must — making sure iconography was implemented wasn’t. Instead of asking the product team what was possible, we worked from a monolith set of features. I was reminded that as we are all sprinting towards the same goal, departments need to work together to cover each other’s blind spots.
Our relationship with marketing
The rebuild aspired to support Entr’s newfound success. Our product team was called in to rebuild the core web product to support their scaling efforts and ultimately their entry into the US market.

Our high level goals were to:

1. Build a faster and easier experience for Hosts and Organisers

2. Turn latest business data into features

3. Improve client retention and client acquisition
Gearing up for the startup roller coaster
I led the product team, design of the user interface and experience of the rebuild.

Through collaboration with founders, I defined the scope and translated business goals into product strategies and features.

Following design, I was the product lead managing the build until launch. I worked closely with the engineering team, founding team, a content strategist and 2 product managers.

In parallel, I led the rebranding effort of the company, working with a brand designer, a graphic designer and the founders.

The app officially launched in August 2018.
My role
In less than a year, the founding team had cleverly hacked their way to a pre-seed — a testament of their successful Canadian entry. As demand was pulling the team into new heights, not the same could be said about the app.

Entr’s two-sided marketplace was now adding venues every day and event planners were flocking to the platform. Entr would sign venues on their platform and assist organisers looking for a space to host their next event.

Their core product, designed and built from the ground up by one of the founders, had now served its purpose. The app was running on Wordpress, hackish plugins, code snippets and creative workarounds… quite far from the traditional blog.

The app had become a Frankenstein.
Agile mindset without the ability
Entr (rebranded as Planned) is a fresh Montreal-based startup making noise in a $500B industry. Founded by two gifted entrepreneurs, the team is disrupting the event planning space with a free turnkey solution for event planners.

I was part of the product rebuild that supported Entr’s most explosive growth to date.
More growth, more problems
Some of our raw information was needed during almost every listing page scan. Size, venue type or capacity were all basic criteria that Organisers looked for when going through a listing, so we made sure they were loud and clear.
Highlights section
An interrogation that kept coming up was related to finding a venue that had the right fit for the event. Even though this could already be deduced from the listing information, Organisers wanted reassurance that their event was not going to create a fuss for the Host.

To respond to this, I worked on an event tagging system to let Organisers know what kinds of events were usually hosted at the venue. My intention was to give confidence early on without having to sift through every section of the listing page.
“Perfect for” section
Another recurring theme was the anxiety related to contacting a venue’s Host, “Will they answer me today?” or “I really hope this goes smoothly…” were fears to address as they were common. To mitigate this, we worked on a venue verification system based on Entr’s observed Host signals, added a response time field to foster prompt replies and a profile picture for Hosts to induce trust with the Organiser.
Over-designing for fears
Entr previously showed the exact location of venues but ultimately reverted to an approach cautious of safety for their Hosts and strictly showed the neighbourhood. This was fine for many corporate planners that had flexible requirements, but not for Organisers (e.g. wedding planners) that needed to account for the venue’s surroundings.

Heavily inspired by Airbnb’s location section, we sought to give out a small (less than 1 km) location radius to be mindful of both parties.
A sense of location
As observed by the team at Entr, images greatly inspired and motivated Organisers when looking for a listing. In order to reflect this insight, we steered away from a single image component to a multiple images component focusing on the venue’s best features.
As observed in our early study, venue owner frustration revealed that we should do more to limit the chat exchanges between both parties. Looking at the redundant questions asked in our chat rooms, we worked on a message Host form to help Hosts have access to basic event information from the start.

Fields included basic information like dates, times and number of attendees. The “What should the owner expect?” section focused on the 3 event features (based on Entr’s insight) that Hosts need to know for logistical and legal reasons.
The initial point of contact
The team at Entr had data to support that the chat page was where users were dropping off in order to conclude deals outside of the platform. Although this was a stress for the team, we still did not want to resort to aggressive tactics like blocking phone numbers or emails during chat exchanges — we knew that users would always find a way to beat the code.

Instead of working against our users, we focused on the aspects that made it logical for Hosts to stay on the platform — robust negotiation tool and secure online payments. The idea was for Hosts to willingly stay on the platform for a product they loved and not because they were forced to.
No dark UX
To have a starting point, I explored how Hosts currently negotiated on Entr. I partnered with the founders to guide my research as they kept close contact with some of their Hosts.

We found that after exchanging with Organisers, most hosts generated their quotes through their external tools (e.g. QuickBooks) to be then sent electronically. Because the quote was sent via email, the rest of the back and forth usually took place in that same environment until the need for payment, which was then handled manually by the Host or Entr. The study uncovered a few design challenges:


1. Without integrating into our Hosts’ accounting softwares, vendors are still going to produce their own invoices for their records.

2. Hosts have complex quote and contract structures that would be costly to mimic and be mindful of all.

3. Some big clients will simply not go digital and will continue to demand manual payments.

With our findings and roadmap in mind, we realised that venturing into a full quoting system was going to be a future ongoing project to improve. In this spirit, I sought to facilitate payment instead of designing for a complete quoting process.
Closing a lead
In order to help conversations stay on track, we worked on a quote summary component displaying basic event information and the breakdown of the cost. This aimed to reduce the observed user frustration when having to search for data in a conversation or having to repeat information from room to room.
Quote summary
After surveying our Hosts’ current payment option, we decided to offer 3 payment options that covered all the bases, including a manual payment option. Since payment had a high potential for dissatisfaction, we opted for the safer option.
Payment options
With facilitating payment in mind, I aimed to build simple but versatile controls to let Hosts manage the bottom line of any quote.

Although our app was going to generate quotes based on Organiser input (e.g. length of the event) and a listing’s settings (e.g. daily rate), it was important to let Hosts be in control of quote breakdowns at all times. To do so, the flow involves going through the quote settings steps from the listing wizard form — with inputs being prefilled to speed up the process.
Basic quote flow
Early on, data revealed how Hosts were reluctant to stay on the phone or complete tedious email templates to register their venue. It was easy to be empathetic — owners were already spread thin as they were managing an ever-changing calendar of events from multiple sources.

Since it wasn’t feasible to create a venue acquisition team to meet with owners and take on the burden of onboarding — we had to resort to a computational approach. The aim was to create a fast and convenient listing form wizard that could be initialised, paused or completed whenever the Host wanted to do so.

The onboarding flow was based on Entr’s new venue acquisition strategy and so we did not have much say on the data that should be taken from venues. After completing a first draft of the wizard, I got a sense of just how big the form was going to be — this stressed me to make every step as simple as possible and give timely tips to our users in order to reduce cognitive effort through the flow.
Better venue acquisition means a better catalogue
With the form still looking like a taunting task, I built a click-through prototype to highlight the form’s weaknesses. After testing the wizard with 3 participants, we found that:


1. Users did not have a sense of progression

2. Users struggled with context switch (e.g. from adding venue images to pricing)

3. Users felt like they could loose their work when leaving the form


To respond to the issues found, I worked on microcopy solutions to address user anxiety:


1. Breadcrumb component grouping similar sub-tasks under 3 steps: basic venue information, listing specific information (e.g. images, title, description) and pricing related information.

2. Dedicated screen showed at the beginning and between every group of questions to inform the users of the incoming groups of questions.

3. Even though progress is saved through out the form, we added an indicator to reassure Hosts that their hard work was not going to waste.

Organiser: Scrolling through a Listing

Organiser: Start of the contact wizard

Organiser: Finding a Listing
Host: Chatting with Organiser
Host: Quote wizard start
Host: Quote sent

Host: Completing the Quote wizard

Credit to lecourrierdusud.ca
Credit to Omar Elgabry
Retrospective
Less than a year later, Entr pivoted to an event-based flow instead of a venue-based approach that was mandated for the rebuild. This could be a case of we told you so but I believe it stems from the general perception of design.
Hierarchies are real
It seems like we have a natural tendency to value design when solving a problem but much less when defining it. We had a hunch, a bit of data but did not fight strongly enough for the pivot. All is well now but I still believe an earlier shift would of been a better move for the product.

With clever founders, I reckon this realisation will induce a strong shift into user centric practices everywhere in the firm. Cheers to seeing the team become a unicorn!
Halfway through the build, the founders managed to score a spot on TV to pitch and promote their product — which would be aired in a few weeks.

We managed to put out a decent beta in time for the show. Under the hood though, code review and commenting had lacked and we knew refactoring tickets were creeping on us.

Although the impact from the appearance is hard to measure, it definitely had a great impact in terms of marketing, exposure and credibility. From a product perspective though, the rush had created a few surprises for the rest of our build.

Not crashing during the expected surge in traffic was a must — making sure iconography was implemented wasn’t. Instead of asking the product team what was possible, we worked from a monolith set of features. I was reminded that as we are all sprinting towards the same goal, departments need to work together to cover each other’s blind spots.
Our relationship with marketing
Epilogue
During the build, it was exciting to see the team grow like a true startup. To sustain the expansion, our product team had to be adaptable as Entr was landing bigger accounts and pitching the product on stages like Y Combinator.

In April 2018, we launched an early beta for Entr’s TV appearance on Dragon’s Den. The full product launched later in August.
The launch
The rebuild helped Entr capitalise on their growth as they were advancing to new markets and growing their user base. Following launch, the app saw significant growth in terms of sales, conversion and user retention.
The results
  Entr raised a seed round of $1.13M from world class investors and VCs
✓  Internal team at Entr grew by 4x
✓  Signed major accounts like l’Oreal, Michael Kors & Bank of Montreal
Our Process
Some of our raw information was needed during almost every listing page scan. Size, venue type or capacity were all basic criteria that Organisers looked for when going through a listing, so we made sure they were loud and clear.
Highlights section
As observed in our early study, venue owner frustration revealed that we should do more to limit the chat exchanges between both parties. Looking at the redundant questions asked in our chat rooms, we worked on a message Host form to help Hosts have access to basic event information from the start.

Fields included basic information like dates, times and number of attendees. The “What should the owner expect?” section focused on the 3 event features (based on Entr’s insight) that Hosts need to know for logistical and legal reasons.
The initial point of contact
The team at Entr had data to support that the chat page was where users were dropping off in order to conclude deals outside of the platform. Although this was a stress for the team, we still did not want to resort to aggressive tactics like blocking phone numbers or emails during chat exchanges — we knew that users would always find a way to beat the code.

Instead of working against our users, we focused on the aspects that made it logical for Hosts to stay on the platform — robust negotiation tool and secure online payments. The idea was for Hosts to willingly stay on the platform for a product they loved and not because they were forced to.
No need for dark UX
To have a starting point, I explored how Hosts currently negotiated on Entr. I partnered with the founders to guide my research as they kept close contact with some of their Hosts.

We found that after exchanging with Organisers, most hosts generated their quotes through their external tools (e.g. QuickBooks) to be then sent electronically. Because the quote was sent via email, the rest of the back and forth usually took place in that same environment until the need for payment, which was then handled manually by the Host or Entr. The study uncovered a few design challenges:


1. Without integrating into our Hosts’ accounting softwares, vendors are still going to produce their own invoices for their records.

2. Hosts have complex quote and contract structures that would be costly to mimic and be mindful of all.

3. Some big clients will simply not go digital and will continue to demand manual payments.

With our findings and roadmap in mind, we realised that venturing into a full quoting system was going to be a future ongoing project to improve. In this spirit, I sought to facilitate payment instead of designing for a complete quoting process.
Closing a lead
In order to help conversations stay on track, we worked on a quote summary component displaying basic event information and the breakdown of the cost. This aimed to reduce the observed user frustration when having to search for data in a conversation or having to repeat information from room to room.
Quote summary
After surveying our Hosts’ current payment option, we decided to offer 3 payment options that covered all the bases, including a manual payment option. Since payment had a high potential for dissatisfaction, we opted for the safer option.
Payment options
With facilitating payment in mind, I aimed to build simple but versatile controls to let Hosts manage the bottom line of any quote.

Although our app was going to generate quotes based on Organiser input (e.g. length of the event) and a listing’s settings (e.g. daily rate), it was important to let Hosts be in control of quote breakdowns at all times. To do so, the flow involves going through the quote settings steps from the listing wizard form — with inputs being prefilled to speed up the process.
Basic quote flow
Early on, data revealed how Hosts were reluctant to stay on the phone or complete tedious email templates to register their venue. It was easy to be empathetic — owners were already spread thin as they were managing an ever-changing calendar of events from multiple sources.

Since it wasn’t feasible to create a venue acquisition team to meet with owners and take on the burden of onboarding — we had to resort to a computational approach. The aim was to create a fast and convenient listing form wizard that could be initialised, paused or completed whenever the Host wanted to do so.

The onboarding flow was based on Entr’s new venue acquisition strategy and so we did not have much say on the data that should be taken from venues. After completing a first draft of the wizard, I got a sense of just how big the form was going to be — this stressed me to make every step as simple as possible and give timely tips to our users in order to reduce cognitive effort through the flow.
Better venue acquisition means a better catalogue
With the form still looking like a taunting task, I created a click-through prototype to highlight the form’s weaknesses. After testing the wizard with 3 participants, we found that:

1. Users did not have a sense of progression

2. Users struggled with context switch (e.g. from adding venue images to pricing)

3. Users felt like they could loose their work when leaving the form


To respond to the issues found, I worked on microcopy solutions to address user anxiety:


1. Breadcrumb component grouping similar sub-tasks under 3 steps: basic venue information, listing specific information (e.g. images, title, description) and pricing related information.

2. Dedicated screen showed at the beginning and between every group of questions to inform the users of the incoming groups of questions.

3. Even though progress is saved through out the form, we added a saved indicator to reassure Hosts that their hard work was not going to waste.
An interrogation that kept coming up was related to finding the venue that had the right fit for the event. Even though this could already be deduced from the listing information, Organisers wanted reassurance that their event was not going to create a fuss for the Host.

To respond to this, I worked on an event tagging system to let Organisers know what kinds of events were usually hosted at the venue. My intention was to give confidence early on without having to sift through every section of the listing page.
“Perfect for” section
Another recurring theme was the anxiety related to contacting a venue’s Host, “Will they answer me today?” or “I really hope this goes smoothly…” were fears to address as they were common. To mitigate this, we worked on a venue verification system based on Entr’s observed Host signals, added a response time field to foster prompt replies and a profile picture for Hosts to induce trust with the Organiser.
Over-designing for fears
Entr previously showed the exact location of venues but ultimately reverted to an approach cautious of safety for their Hosts and strictly showed the neighbourhood. This was fine for many corporate planners that had flexible requirements, but not for Organisers (e.g. wedding planners) that needed to account for the venue’s surroundings.

Heavily inspired by Airbnb’s location section, we sought to give out a small (less than 1 km) location radius to be mindful of both parties.
A sense of location
As observed by the team at Entr, images greatly inspired and motivated Organisers when looking for a listing. In order to reflect this insight, we steered away from a single image component to a multiple images component focusing on the venue’s best features.
We had clues from our studies on what the listing page lacked but it was still fuzzy. To have a grasp of the organiser thought process, I ran a small think-aloud exercise with 5 participants that focused solely on the listing page. My aim was to use these findings to redesign the listing page and its parent — the search page.

The study revealed that our participants were mostly struggling to find information that was already there. Questions like “Is the space capacity large enough for my event?” and “Is there a minimum of hours for a rental?” could all technically be answered but required more thinking than it should.

Going forward, I explored ways to rearrange existing information to reduce the time needed by Organisers when going through a listing.
Give the right information and only the right information
When looking at Entr’s current value proposition, it was currently skewed in favour of Organisers. The core product was not doing much for venue owners and it had been felt through out our early studies. I was confident that being mindful of both sides of the marketplace was going to trickle-down positively in the overall product experience.
Turning data into new features
The chat was integrated into the product, but did not have much perceived added value for Hosts. It was a must-have feature, but not one that delighted our users. In order to save time, minimise mistakes and induce more sales, I worked on a quote flow tackling the most time consuming activity for Hosts — closing a sale.
Less focus on the chat, more on the event
Going forward with design, two questions informed my strategy:

1. How do we induce better, faster and easier venue bookings?
2. How can we improve the value proposition for everyone?

Early on, it was important to leverage our latest discoveries. The first area I set out to rethink was the first steps for every event planner — choosing the right venue.
Better event creation for everyone
Our Solution
Entr makes sure that you always know what you are paying for, regardless of the amount of changes when negotiating. Review and pay online when ready, having the peace of mind that what you see is what you get.
No surprises when taking out your wallet
Entr saves you time by telling you early on what you can do and what to expect. After choosing a space, give us your schedule and attendees and we’ll instantly get you an initial quote.

At Entr, you can message venue owners with confidence knowing that you are both on the same page from the start.
We are your booking assistant
Entr is more than an app, it’s a group of event experts that know the complexity of creating great events. We are here to inspire and give you confidence that Entr is the right tool for the job. We cannot wait to see what you’ll do with our spaces.
New product, new identity
Entr is here to help your next event be a success. Explore exclusive event spaces and get to know the important details before any commitment.

Entr helps you secure the best deal and ensures peace of mind so you can focus on delivering the best event.
Rebuild of the core Entr app
Stepping Back
A significant portion of our Hosts did not see Entr as more than a lead generator. Because Hosts felt like the app was basically a matching system, they were inclined to work outside of the platform and expressed behaviour that could corrupt some of Entr’s most active Organisers.

We asked ourselves the simplest question, how could we help users organise and host events in a better way? Our proposal was the complete redesign of their core product.
Unclear value proposition caused app-wide issues
More Findings
Entr observed that venue browsing had a special role for Organisers. A coveted location, beautiful mezzanine or magical entrance were all features that sparked ideas and made events real for Organisers.
Venues are truly important
Organisers are the ones initialising conversations with Hosts and currently had the most incentives to complete their booking. Data revealed that Hosts were often slow in their replies and forced Organisers to look outside of their top venue options or the platform altogether.
Hosts are missing out on sales
The chat page was the leading drop-off point for our conversion flow. Hosts who did not feel like they were receiving enough value would encourage the other party to leave the platform and bypass Entr’s fee structure.
Loss of clients
Acquiring new venues is a driving KPI for Entr as a complete catalogue played an important role in their marketing strategy. Entr did not currently have the resources to go to venues themselves for registration and had to call or email venues — which seemed to annoy most vendors as it was a time investment with no guaranteed return.
Signing up new venues is crucial
Our initial study sparked clues and ideas but I now set out to understand the specific event planning reality shared by all of our users and prospects.

Since I was working with a team that had a real passion to help create great events and grow their vendors’ businesses, the founders were keeping close relationships with many of their Hosts and Organisers.

I partnered with the technical founder to gather the quantitative and qualitative data that the team had collected up to now. My aim was to gain a better understanding of the hopes and struggles of our users that had been documented by the team.
Understanding the event planning space
Our Discovery
From the small study, it seemed like there was an issue beneath the scope of features. Thinking holistically, the heart and soul of the firm was event planning but the app did not follow through — it was a venue booking tool.

As I thought I discovered an opportunity to involve any and all event related vendors — diving into Entr’s non-digital activities showed that the team was far from leaving that money on the table. Entr had been manually upselling Organisers with catering and audiovisual services since inception.

With data to back up my assumption, I was ready to scrap our Airbnb style flow entirely and design based on events being planned from idea to completion and beyond. Although my hypothesis resonated with the founders, it meant drastic changes for the firm and ultimately for them, did not feel like a necessary thing to do at the time.

Instead of focusing on what we could do, we turned to the original plan for the core product rebuild — making an awesome tool that fostered great events.
UX is not aligned with business strategy
Project Kickoff
At the start of the project, we focused on getting a grasp of the health of the current experience for Hosts and Organisers. Since a vast majority of Entr’s users were professionals who used the tool daily and had found their own ways around the product, my aim was to generate insight that was inclusive of current but also new users.

When planning the study, I set out to test the app with 6 participants who had little to no prior knowledge of the platform. Organisers were tasked to book a listing and Hosts to close an incoming lead — both were given user scenarios to guide their experience.
Early investigation
When talking about the app, organisers felt that they were booking a venue rather than planning their event.
Wrong user mindset
Hosts had to repeat much of the same information from conversation to conversation and had to search through chat rooms when preparing a quote (e.g. dates and start/end times).
Inefficient lead process
Since payments were handled manually outside of the platform, it was hard for Hosts and Organisers to feel secure about their booking.
Cheques and phone calls
When Hosts were tasked with closing their lead, all they could do was chat. No negotiation process was in place and extra documentation had to be sent over email.
Unassisted negotiation
The listing feed was frustrating Organisers during their search. Loading images felt too long (especially on mobile) and created confusion as UI elements were blank (i.e. no lazy loading).
Performance issue
Our Problem
I led the product team, design of the user interface and experience of the rebuild.

Through collaboration with founders, I defined the scope and translated business goals into product strategies and features.

Following design, I was the product lead managing the build until launch. I worked closely with the engineering team, founding team, a content strategist and 2 product managers.

In parallel, I led the rebranding effort of the company, working with a brand designer, a graphic designer and the founders.

The app officially launched in August 2018.
My role
The rebuild aspired to support Entr’s newfound success. Our product team was called in to rebuild the core web product to support their scaling efforts and ultimately their entry into the US market.

Our high level goals were to:

1. Build a faster and easier experience for Hosts and Organisers
2. Turn latest business data into features
3. Improve client retention and client acquisition
Gearing up for the startup roller coaster
Prologue
In less than a year, the founding team had cleverly hacked their way to a pre-seed — a testament of their successful Canadian entry. As demand was pulling the team into new heights, not the same could be said about the app.

Entr’s two-sided marketplace was now adding venues every day and event planners were flocking to the platform. Entr would sign venues on their platform and assist organisers looking for a space to host their next event.

Their core product, designed and built from the ground up by one of the founders, had now served its purpose. The app was running on Wordpress, hackish plugins, code snippets and creative workarounds… quite far from the traditional blog.

The app had become a Frankenstein.
Agile mindset without the ability

Organiser: Scrolling through a Listing

Organiser: Finding a Listing

Organiser: Start of the contact wizard

Host: Chatting with Organiser
Host: Quote wizard start

Host: Completing the Quote wizard

Host: Quote sent
Credit to lecourrierdusud.ca
Credit to Omar Elgabry
Entr (rebranded as Planned) is a fresh Montreal-based startup making noise in a $500B industry. Founded by two gifted entrepreneurs, the team is disrupting the event planning space with a free turnkey solution for event planners.

I was part of the product rebuild that supported Entr’s most explosive growth to date.
More growth, more problems
Retrospective
Epilogue
Our Process
Some of our raw information was needed during almost every listing page scan. Size, venue type or capacity were all basic criteria that Organisers looked for when going through a listing, so we made sure they were loud and clear.
Highlights section
An interrogation that kept coming up was related to finding the venue that had the right fit for the event. Even though this could already be deduced from the listing information, Organisers wanted reassurance that their event was not going to create a fuss for the Host.

To respond to this, I worked on an event tagging system to let Organisers know what kinds of events were usually hosted at the venue. My intention was to give confidence early on without having to sift through every section of the listing page.
“Perfect for” section
Another recurring theme was the anxiety related to contacting a venue’s Host, “Will they answer me today?” or “I really hope this goes smoothly…” were fears to address as they were common. To mitigate this, we worked on a venue verification system based on Entr’s observed Host signals, added a response time field to foster prompt replies and a profile picture for Hosts to induce trust with the Organiser.
Over-designing for fears
Entr previously showed the exact location of venues but ultimately reverted to an approach cautious of safety for their Hosts and strictly showed the neighbourhood. This was fine for many corporate planners that had flexible requirements, but not for Organisers (e.g. wedding planners) that needed to account for the venue’s surroundings.

Heavily inspired by Airbnb’s location section, we sought to give out a small (less than 1 km) location radius to be mindful of both parties.
A sense of location
As observed by the team at Entr, images greatly inspired and motivated Organisers when looking for a listing. In order to reflect this insight, we steered away from a single image component to a multiple images component focusing on the venue’s best features.
As observed in our early study, venue owner frustration revealed that we should do more to limit the chat exchanges between both parties. Looking at the redundant questions asked in our chat rooms, we worked on a message Host form to help Hosts have access to basic event information from the start.

Fields included basic information like dates, times and number of attendees. The “What should the owner expect?” section focused on the 3 event features (based on Entr’s insight) that Hosts need to know for logistical and legal reasons.
The initial point of contact
The team at Entr had data to support that the chat page was where users were dropping off in order to conclude deals outside of the platform. Although this was a stress for the team, we still did not want to resort to aggressive tactics like blocking phone numbers or emails during chat exchanges — we knew that users would always find a way to beat the code.

Instead of working against our users, we focused on the aspects that made it logical for Hosts to stay on the platform — robust negotiation tool and secure online payments. The idea was for Hosts to willingly stay on the platform for a product they loved and not because they were forced to.
No need for dark UX
To have a starting point, I explored how Hosts currently negotiated on Entr. I partnered with the founders to guide my research as they kept close contact with some of their Hosts.

We found that after exchanging with Organisers, most hosts generated their quotes through their external tools (e.g. QuickBooks) to be then sent electronically. Because the quote was sent via email, the rest of the back and forth usually took place in that same environment until the need for payment, which was then handled manually by the Host or Entr. The study uncovered a few design challenges:


1. Without integrating into our Hosts’ accounting softwares, vendors are still going to produce their own invoices for their records.

2. Hosts have complex quote and contract structures that would be costly to mimic and be mindful of all.

3. Some big clients will simply not go digital and will continue to demand manual payments.

With our findings and roadmap in mind, we realised that venturing into a full quoting system was going to be a future ongoing project to improve. In this spirit, I sought to facilitate payment instead of designing for a complete quoting process.
Closing a lead
In order to help conversations stay on track, we worked on a quote summary component displaying basic event information and the breakdown of the cost. This aimed to reduce the observed user frustration when having to search for data in a conversation or having to repeat information from room to room.
Quote summary
After surveying our Hosts’ current payment option, we decided to offer 3 payment options that covered all the bases, including a manual payment option. Since payment had a high potential for dissatisfaction, we opted for the safer option.
Payment options
With facilitating payment in mind, I aimed to build simple but versatile controls to let Hosts manage the bottom line of any quote.

Although our app was going to generate quotes based on Organiser input (e.g. length of the event) and a listing’s settings (e.g. daily rate), it was important to let Hosts be in control of quote breakdowns at all times. To do so, the flow involves going through the quote settings steps from the listing wizard form — with inputs being prefilled to speed up the process.
Basic quote flow
Early on, data revealed how Hosts were reluctant to stay on the phone or complete tedious email templates to register their venue. It was easy to be empathetic — owners were already spread thin as they were managing an ever-changing calendar of events from multiple sources.

Since it wasn’t feasible to create a venue acquisition team to meet with owners and take on the burden of onboarding — we had to resort to a computational approach. The aim was to create a fast and convenient listing form wizard that could be initialised, paused or completed whenever the Host wanted to do so.

The onboarding flow was based on Entr’s new venue acquisition strategy and so we did not have much say on the data that should be taken from venues. After completing a first draft of the wizard, I got a sense of just how big the form was going to be — this stressed me to make every step as simple as possible and give timely tips to our users in order to reduce cognitive effort through the flow.
Better venue acquisition means a better catalogue
With the form still looking like a taunting task, I created a click-through prototype to highlight the form’s weaknesses. After testing the wizard with 3 participants, we found that:


1. Users did not have a sense of progression

2. Users struggled with context switch (e.g. from adding venue images to pricing)

3. Users felt like they could loose their work when leaving the form

To respond to the issues found, I worked on microcopy solutions to address user anxiety:


1. Breadcrumb component grouping similar sub-tasks under 3 steps: basic venue information, listing specific information (e.g. images, title, description) and pricing related information.

2. Dedicated screen showed at the beginning and between every group of questions to inform the users of the incoming groups of questions.

3. Even though progress is saved through out the form, we added an indicator to reassure Hosts that their hard work was not going to waste.
Our Solution
Stepping Back
More Findings
Our Discovery
Project Kickoff
Our Problem
Prologue
Less than a year later, Entr pivoted to an event-based flow instead of a venue-based approach that was mandated for the rebuild. This could be a case of we told you so but I believe it stems from the general perception of design.
Hierarchies are a real thing
It seems like we have a natural tendency to value design when solving a problem but much less when defining it. We had a hunch, a bit of data but did not fight strongly enough for the pivot. All is well now but I still believe an earlier shift would of been a better move for the product.

With clever founders, I reckon this realisation will induce a strong shift into user centric practices everywhere in the firm. Cheers to seeing the team become a unicorn, good luck guys!
Halfway through the build, the founders managed to score a spot on TV to pitch and promote their product — which would be aired in a few weeks.

We managed to put out a decent beta in time for the show. Under the hood though, code review and commenting had lacked and we knew refactoring tickets were creeping on us.

Although the impact from the appearance is hard to measure, it definitely had a great impact in terms of marketing, exposure and credibility. From a product perspective though, the rush had created a few surprises for the rest of our build.

Not crashing during the expected surge in traffic was a must — making sure iconography was implemented wasn’t. Instead of asking the product team what was possible, we worked from a monolith set of features. I was reminded that as we are all sprinting towards the same goal, departments need to work together to cover each other’s blind spots.
Our relationship with marketing
During the build, it was exciting to see the team grow like a true startup. To sustain the expansion, our product team had to be adaptable as Entr was landing bigger accounts and pitching the product on stages like Y Combinator.

In April 2018, we launched an early beta for Entr’s TV appearance on Dragon’s Den. The full product launched later in August.
The launch
The rebuild helped Entr capitalise on their growth as they were advancing to new markets and growing their user base. Following launch, the app saw significant growth in terms of sales, conversion and user retention.
The results
  Entr raised a seed round of $1.13M from world class investors and VCs
✓  Internal team at Entr grew by 4x
✓  Signed major accounts like l’Oreal, Michael Kors & Bank of Montreal
We had clues from our studies on what the listing page lacked but it was still fuzzy. To have a grasp of the organiser thought process, I ran a small think-aloud exercise with 5 participants that focused solely on the listing page. My aim was to use these findings to redesign the listing page and its parent — the search page.

The study revealed that our participants were mostly struggling to find information that was already there. Questions like “Is the space capacity large enough for my event?” and “Is there a minimum of hours for a rental?” could all technically be answered but required more thinking than it should.

Going forward, I explored ways to rearrange existing information to reduce the time needed by Organisers when going through a listing.
Give the right information and only the right information
When looking at Entr’s current value proposition, it was currently skewed in favour of Organisers. The core product was not doing much for venue owners and it had been felt through out our early studies. I was confident that being mindful of both sides of the marketplace was going to trickle-down positively in the overall product experience.
Turning data into new features
The chat was integrated into the product, but did not have much perceived added value for Hosts. It was a must-have feature, but not one that delighted our users. In order to save time, minimise mistakes and induce more sales, I worked on a quote flow tackling the most time consuming activity for Hosts — closing a sale.
Less focus on the chat, more on the event
Going forward with design, two questions informed my strategy:

1. How do we induce better, faster and easier venue bookings?
2. How can we improve the value proposition for everyone?

Early on, it was important to leverage our latest discoveries. The first area I set out to rethink was the first steps for every event planner — choosing the right venue.  
Better event creation for everyone
Entr makes sure that you always know what you are paying for, regardless of the amount of changes when negotiating. Review and pay online when ready, having the peace of mind that what you see is what you get.
No surprises when taking out your wallet
Entr saves you time by telling you early on what you can do and what to expect. After choosing a space, give us your schedule and attendees and we’ll instantly get you an initial quote.

At Entr, you can message venue owners with confidence knowing that you are both on the same page from the start.
We are your booking assistant
Entr is more than an app, it’s a group of event experts that know the complexity of creating great events. We are here to inspire and give you confidence that Entr is the right tool for the job. We cannot wait to see what you’ll do with our spaces.
New product, new identity
Entr is here to help your next event be a success. Explore exclusive event spaces and get to know the important details before any commitment.

Entr helps you secure the best deal and ensures peace of mind so you can focus on delivering the best event.
Rebuild of the core Entr app
A significant portion of our Hosts did not see Entr as more than a lead generator. Because Hosts felt like the app was basically a matching system, they were inclined to work outside of the platform and expressed behaviour that could corrupt some of Entr’s most active Organisers.

We asked ourselves the simplest question, how could we help users organise and host events in a better way? Our proposal was the complete redesign of their core product.
Unclear value proposition caused app-wide issues
Entr observed that venue browsing had a special role for Organisers. A coveted location, beautiful mezzanine or magical entrance were all features that sparked ideas and made events real for Organisers.
Venues are truly important
Organisers are the ones initialising conversations with Hosts and currently had the most incentives to complete their booking. Data revealed that Hosts were often slow in their replies and forced Organisers to look outside of their top venue options or the platform altogether.
Hosts are missing out on sales
The chat page was the leading drop-off point for our conversion flow. Hosts who did not feel like they were receiving enough value would encourage the other party to leave the platform and bypass Entr’s fee structure.
Loss of clients
Acquiring new venues is a driving KPI for Entr. The team did not have the resources to go to venues themselves for registration and had to call or email venues — which seemed to annoy most vendors as it was a time investment with no guaranteed return.
Signing up new venues is crucial
Our initial study sparked clues and ideas but I now set out to understand the specific event planning reality shared by all of our users and prospects.

Since I was working with a team that had a real passion to help create great events and grow their vendors’ businesses, the founders were keeping close relationships with many of their Hosts and Organisers.

I partnered with the technical founder to gather the quantitative and qualitative data that the team had collected up to now. My aim was to gain a better understanding of the hopes and struggles of our users that had been documented by the team.
Understanding the event planning space
From the small study, it seemed like there was an issue beneath the scope of features. Thinking holistically, the heart and soul of the firm was event planning but the app did not follow through — it was a venue booking tool.

As I thought I discovered an opportunity to involve any and all event related vendors — diving into Entr’s non-digital activities showed that the team was far from leaving that money on the table. Entr had been manually upselling Organisers with catering and audiovisual services since inception.

With data to back up my assumption, I was ready to scrap our Airbnb style flow entirely and design based on events being planned from idea to completion and beyond. Although my hypothesis resonated with the founders, it meant drastic changes for the firm and ultimately for them, did not feel like a necessary thing to do at the time.

Instead of focusing on what we could do, we turned to the original plan for the core product rebuild — making an awesome tool that fostered great events.
UX is not aligned with business strategy
At the start of the project, we focused on getting a grasp of the health of the current experience for Hosts and Organisers. Since a vast majority of Entr’s users were professionals who used the tool daily and had found their own ways around the product, my aim was to generate insight that was inclusive of current but also new users.

When planning the study, I set out to test the app with 6 participants who had little to no prior knowledge of the platform. Organisers were tasked to book a listing and Hosts to close an incoming lead — both were given user scenarios to guide their experience.
Early investigation
When talking about the app, organisers felt that they were booking a venue rather than planning their event.
Wrong user mindset
Hosts had to repeat much of the same information from conversation to conversation and had to search through chat rooms when preparing a quote (e.g. dates and start/end times).
Inefficient lead process
Since payments were handled manually outside of the platform, it was hard for Hosts and Organisers to feel secure about their booking.
Cheques and phone calls
When Hosts were tasked with closing their lead, all they could do was chat. No negotiation process was in place and extra documentation had to be sent over email.
Unassisted negotiation
The listing feed was frustrating Organisers during their search. Loading images felt too long (especially on mobile) and created confusion as UI elements were blank (i.e. no lazy loading).
Performance issue
I led the product team, design of the user interface and experience of the rebuild.

Through collaboration with founders, I defined the scope and translated business goals into product strategies and features.

Following design, I was the product lead managing the build until launch. I worked closely with the engineering team, founding team, a content strategist and 2 product managers.

In parallel, I led the rebranding effort of the company, working with a brand designer, a graphic designer and the founders.

The app officially launched in August 2018.
My role
The rebuild aspired to support Entr’s newfound success. Our product team was called in to rebuild the core web product to support their scaling efforts and ultimately their entry into the US market.

Our high level goals were to:

1. Build a faster and easier experience for Hosts and Organisers
2. Turn latest business data into features
3. Improve client retention and client acquisition
Gearing up for the startup roller coaster
In less than a year, the founding team had cleverly hacked their way to a pre-seed — a testament of their successful Canadian entry. As demand was pulling the team into new heights, not the same could be said about the app.

Entr’s two-sided marketplace was now adding venues every day and event planners were flocking to the platform. Entr would sign venues on their platform and assist organisers looking for a space to host their next event.

Their core product, designed and built from the ground up by one of the founders, had now served its purpose. The app was running on Wordpress, hackish plugins, code snippets and creative workarounds… quite far from the traditional blog.

The app had become a Frankenstein.
Agile mindset without the ability
Entr (rebranded as Planned) is a fresh Montreal-based startup making noise in a $500B industry. Founded by two gifted entrepreneurs, the team is disrupting the event planning space with a free turnkey solution for event planners.

I was part of the product rebuild that supported Entr’s most explosive growth to date.
More growth, more problems

Organiser: Scrolling through a Listing

Organiser: Start of the contact wizard

Host: Chatting with Organiser
Host: Quote wizard start

Host: Completing the Quote wizard

Host: Quote sent
Credit to lecourrierdusud.ca
Credit to Omar Elgabry
Organiser: Finding a Listing