Marcus White
Bold Penguin
First Time Wizard Agent Onboarding v2
Context
Bold Penguin's core quoting platform (Terminal) enables commercial insurance agents to quickly quote and bind policies from multiple carriers through a single, streamlined digital platform. Bold Penguin is now introducing a new in-house agency—Bold Penguin Placement Desk—that allows agents to get quotes without requiring carrier appointments. This creates an opportunity to reimagine the onboarding experience for new agents, enabling them to take advantage of this new feature immediately upon signing up.
Problem
The current onboarding experience is too lengthy and confusing for new users. This puts additional burden on our customer success teams, who must manually explain the Terminal's capabilities to new agents.
Goal
To streamline agent onboarding and reduce time-to-value in the Bold Penguin Terminal by efficiently guiding new users through account creation, quoting processes, compliance requirements, and commission setup;
- Initial sign-ups should take 60 seconds or less.
- From sign-up to first quote should take 5 minutes or less.
- Compliance approval should take 1 hour or less.
Role
Design Manager
Team:
2 Product Designers
1 Product Owner
1 Director of Product
1 Engineering Team
Timeline:
Q2 2025
Final result preview
View Live Prototype
Discovery
What we started with
- We started with an initial meeting to understand the Bold Penguin Placement Desk and align it with our specific milestone goals for our revamped onboarding efforts.
- The Bold Penguin Placement Desk is a new in-house agency initiative that allows agents to quote and bind policies without requiring carrier appointments. This feature helps agents serve their clients faster, increase agency revenue, streamline policy placement, and enhance operational efficiency.
- The fastest recorded completion time for the current onboarding experience is approximately 2 minutes and 12 seconds.
- Our new goal is to reduce initial sign-up to less than 60 seconds, meaning the agent has created an account and verified their email.
- From sign-up to first quote, we aim to keep the process under five minutes, meaning the agent has successfully submitted their first application form quote.
- We want compliance approval to take less than an hour, meaning the agent has completed all compliance tasks required for commission eligibility.
What was created and the thought process behind it
- We created personas for the types of agents who would enter this new onboarding flow and identified their various starting points.
- We mapped out the different user journeys needed from our current flow:
- A standard flow where the new user signs up first, pays second, and quotes third
- An expedited flow where the new user signs up first, quotes second, and pays third
- A biBERK x Placement Desk flow where agents enter the Terminal for the first time as referrals from biBERK phone agents
What we delivered
- A clear outline for what we needed to design in user flow and low fidelity wireframes for the standard flow and expedited flow.
Initial Design Review
What we started with
- User flows for both the standard flow and the expedited flow, outlining all steps in the onboarding process.
- Lack of clarity about how Bold Penguin Placement Desk would integrate into either of the outlined flows.
What was created and the thought process behind it
- After numerous discussions and feedback sessions, we evaluated the logical sequence for steps within the expedited flow and determined which elements could be eliminated.
- I made the decision to keep only essential steps within the signup portion and move all other steps into the terminal as a checklist for agents to complete at their own pace. The essential steps we decided on were:
- Create your account
- Verify your account
- Create your password
- Tell us about your agency
- Review your subscription
- Enter your payment details
- I advocated for this approach by highlighting best practices from other successful onboarding experiences. I demonstrated how it's standard practice to minimize signup steps—collecting only name, email, and password, followed by plan selection and payment. All remaining setup tasks can then be completed after account creation when users have full access to the platform. This approach significantly streamlines the initial onboarding experience.
What we delivered
- A high-fidelity mockup of the standard flow, outlining all stages of the onboarding experience divided into six key sections:
- Onboarding
- Intercom tour
- Application
- Wholesale submission
- Terminal Checklist tasks
- Bind process
- Through additional discussions, we gained clearer understanding of the Bold Penguin Placement Desk capabilities and how they integrate with the onboarding process. We incorporated this functionality into the mockups, specifically within the wholesale submission and binding process sections.
Feedback Design Review
What we started with
- Through several feedback sessions, I provided critique to our associate product designer on polishing the mockups for presentation to our director of product. Since these were high-fidelity mockups, they needed to be impeccable to effectively highlight our previous discussions. The refined designs clearly helped stakeholders understand the visual elements and copywriting, showing exactly what users would do at each step while setting appropriate expectations.
- We decided to remove the expedited flow to limit the complexity and focus primarily on the standard flow.
What was created and the thought process behind it
- The standard flow has now been revised into five final steps that the agent will be guided through in their first experience diving in the terminal:
- Onboarding: A streamlined process that guides new users through account creation, email verification, agency information collection, plan selection, and payment submission to quickly establish their Bold Penguin Terminal access.
- Intercom Tour: Guides the agent through a concise six-step product tour, highlighting essential navigation elements and key features they'll need on the home dashboard.
- Start First Application & Wholesale Submission: This enables agents to start their first application regardless of carrier appointment status. Upon initial use of the terminal, the Bold Penguin Placement Desk is automatically activated, giving agents immediate access to specific carriers through wholesale channels.
- Terminal Setup Tasks: My task panel on the home dashboard, which guides to a task page outlining all of the outstanding things that the agent needs to do, the properly set up their terminal for the principal as well as producer agents.
- Terminal Setup Complete: We want to define success when the agent has completed all of their terminal set of tasks and received their first application quote, bound the policy and received the commission as a best case scenario
- By creating the terminal setup task page, we developed a solution to address what made the previous onboarding experience so lengthy. This page served as a practical workaround that eliminated the need to build an entirely new notifications menu—a feature we internally recognized as necessary but beyond the scope of this project.
What we delivered
- A design prototype to gather stakeholder feedback for fine-tuning before developer handoff. We prioritized the task sequence on the terminal setup page and refined the copywriting for carrier appointments. Our focus was on clearly communicating to agents what actions needed to be taken and their relative urgency.
- The development team identified an issue with our implementation of new settings pages in the main menu. These pages were separated between tabs anchored by two different settings pages. This created a permissions challenge, as permissions would need to be applied at the tab level rather than the standard page level. After collaboration between design and engineering, we simplified the solution by removing the tabs entirely and making settings pages directly accessible through the menu.
- After meeting with the development team, we presented two options for implementing terminal tasks. Option A involved creating a dedicated terminal task page that would outline all setup requirements. Option B proposed integrating these tasks within a new notifications menu available to all terminal users, which would passively display pending tasks and allow users to navigate directly to the relevant page by clicking on each item. Our developers confirmed that both options would require equal implementation effort. Since Option B offered superior user experience, we decided to proceed with the notifications menu approach.
Final Outcome & Results
View Live Prototype
What was shipped
- A new onboarding experience with drastically less steps to take for the user to submit their payment and get access to the term of the payment.
- A notifications menu within terminal loaded with all the tasks the new user needs to complete to properly set up their terminal.
- A new Placement Desk feature enabled upon the start of a new terminal.
The business value
- Conversion Rate:
- Funnel Analysis: Percentage of users that sign up in 60 seconds or less = 0.9% of users YTD
- Funnel Analysis: Percentage of users that got their first quote in 5 minutes or less = 11% of users YTD
- Funnel Analysis: Percentage of Placement Desk completed quotes vs all other quotes = 1.17% of user for pilot 30 days
The user value
- Time to First Quote:
- Show percentage of users who got their first quote within 24 hours = 22.7%
The data supporting the value delivered
Reflection
What worked well
- As a design and product team, we created an excellent solution to our onboarding challenges by removing numerous steps from the first-time wizard and relocating them to individual tasks accessible after terminal launch. The primary goal of effective onboarding is twofold: get users started quickly and implement mechanisms to re-engage those who abandon the process midway.
- A key insight from this project was recognizing our urgent need for a notifications menu. The success of our onboarding redesign ultimately depends on our ability to re-engage users through notifications, push alerts, and email sequences that prompt them to complete important setup actions. This notification system will be essential for properly measuring and quantifying the success of our new approach.
What could be improved
- This was one of my first projects as a design manager, guiding our junior designer who wanted to lead the end-to-end design process. Despite initial hesitation, I mentored them throughout this substantial effort, focusing on reviewing their user flows, wireframes, and mockups at various fidelity levels while providing specific improvement feedback. Another challenge was working with our junior product owner who became overwhelmed managing multiple stakeholders and priorities. I often needed to step in and help make critical decisions to keep the project on schedule. Overall, this proved to be a valuable learning experience.
Marcus White
Home
Bold Penguin
First Time Wizard Agent Onboarding v2
Context
Bold Penguin's core quoting platform (Terminal) enables commercial insurance agents to quickly quote and bind policies from multiple carriers through a single, streamlined digital platform. Bold Penguin is now introducing a new in-house agency—Bold Penguin Placement Desk—that allows agents to get quotes without requiring carrier appointments. This creates an opportunity to reimagine the onboarding experience for new agents, enabling them to take advantage of this new feature immediately upon signing up.
Problem
The current onboarding experience is too lengthy and confusing for new users. This puts additional burden on our customer success teams, who must manually explain the Terminal's capabilities to new agents.
Goal
To streamline agent onboarding and reduce time-to-value in the Bold Penguin Terminal by efficiently guiding new users through account creation, quoting processes, compliance requirements, and commission setup;
- Initial sign-ups should take 60 seconds or less.
- From sign-up to first quote should take 5 minutes or less.
- Compliance approval should take 1 hour or less.
Role
Design Manager
Team:
2 Product Designers
1 Product Owner
1 Director of Product
1 Engineering Team
Timeline:
Q2 2025
Final result preview
View Live Prototype
Discovery
What we started with
- We started with an initial meeting to understand the Bold Penguin Placement Desk and align it with our specific milestone goals for our revamped onboarding efforts.
- The Bold Penguin Placement Desk is a new in-house agency initiative that allows agents to quote and bind policies without requiring carrier appointments. This feature helps agents serve their clients faster, increase agency revenue, streamline policy placement, and enhance operational efficiency.
- The fastest recorded completion time for the current onboarding experience is approximately 2 minutes and 12 seconds.
- Our new goal is to reduce initial sign-up to less than 60 seconds, meaning the agent has created an account and verified their email.
- From sign-up to first quote, we aim to keep the process under five minutes, meaning the agent has successfully submitted their first application form quote.
- We want compliance approval to take less than an hour, meaning the agent has completed all compliance tasks required for commission eligibility.
What was created and the thought process behind it
- We created personas for the types of agents who would enter this new onboarding flow and identified their various starting points.
- We mapped out the different user journeys needed from our current flow:
- A standard flow where the new user signs up first, pays second, and quotes third
- An expedited flow where the new user signs up first, quotes second, and pays third
- A biBERK x Placement Desk flow where agents enter the Terminal for the first time as referrals from biBERK phone agents
What we delivered
- A clear outline for what we needed to design in user flow and low fidelity wireframes for the standard flow and expedited flow.
Initial Design Review
What we started with
- User flows for both the standard flow and the expedited flow, outlining all steps in the onboarding process.
- Lack of clarity about how Bold Penguin Placement Desk would integrate into either of the outlined flows.
What was created and the thought process behind it
- After numerous discussions and feedback sessions, we evaluated the logical sequence for steps within the expedited flow and determined which elements could be eliminated.
- I made the decision to keep only essential steps within the signup portion and move all other steps into the terminal as a checklist for agents to complete at their own pace. The essential steps we decided on were:
- Create your account
- Verify your account
- Create your password
- Tell us about your agency
- Review your subscription
- Enter your payment details
- I advocated for this approach by highlighting best practices from other successful onboarding experiences. I demonstrated how it's standard practice to minimize signup steps—collecting only name, email, and password, followed by plan selection and payment. All remaining setup tasks can then be completed after account creation when users have full access to the platform. This approach significantly streamlines the initial onboarding experience.
What we delivered
- A high-fidelity mockup of the standard flow, outlining all stages of the onboarding experience divided into six key sections:
- Onboarding
- Intercom tour
- Application
- Wholesale submission
- Terminal Checklist tasks
- Bind process
- Through additional discussions, we gained clearer understanding of the Bold Penguin Placement Desk capabilities and how they integrate with the onboarding process. We incorporated this functionality into the mockups, specifically within the wholesale submission and binding process sections.
Feedback Design Review
What we started with
- Through several feedback sessions, I provided critique to our associate product designer on polishing the mockups for presentation to our director of product. Since these were high-fidelity mockups, they needed to be impeccable to effectively highlight our previous discussions. The refined designs clearly helped stakeholders understand the visual elements and copywriting, showing exactly what users would do at each step while setting appropriate expectations.
- We decided to remove the expedited flow to limit the complexity and focus primarily on the standard flow.
What was created and the thought process behind it
- The standard flow has now been revised into five final steps that the agent will be guided through in their first experience diving in the terminal:
- Onboarding: A streamlined process that guides new users through account creation, email verification, agency information collection, plan selection, and payment submission to quickly establish their Bold Penguin Terminal access.
- Intercom Tour: Guides the agent through a concise six-step product tour, highlighting essential navigation elements and key features they'll need on the home dashboard.
- Start First Application & Wholesale Submission: This enables agents to start their first application regardless of carrier appointment status. Upon initial use of the terminal, the Bold Penguin Placement Desk is automatically activated, giving agents immediate access to specific carriers through wholesale channels.
- Terminal Setup Tasks: My task panel on the home dashboard, which guides to a task page outlining all of the outstanding things that the agent needs to do, the properly set up their terminal for the principal as well as producer agents.
- Terminal Setup Complete: We want to define success when the agent has completed all of their terminal set of tasks and received their first application quote, bound the policy and received the commission as a best case scenario
- By creating the terminal setup task page, we developed a solution to address what made the previous onboarding experience so lengthy. This page served as a practical workaround that eliminated the need to build an entirely new notifications menu—a feature we internally recognized as necessary but beyond the scope of this project.
What we delivered
- A design prototype to gather stakeholder feedback for fine-tuning before developer handoff. We prioritized the task sequence on the terminal setup page and refined the copywriting for carrier appointments. Our focus was on clearly communicating to agents what actions needed to be taken and their relative urgency.
- The development team identified an issue with our implementation of new settings pages in the main menu. These pages were separated between tabs anchored by two different settings pages. This created a permissions challenge, as permissions would need to be applied at the tab level rather than the standard page level. After collaboration between design and engineering, we simplified the solution by removing the tabs entirely and making settings pages directly accessible through the menu.
- After meeting with the development team, we presented two options for implementing terminal tasks. Option A involved creating a dedicated terminal task page that would outline all setup requirements. Option B proposed integrating these tasks within a new notifications menu available to all terminal users, which would passively display pending tasks and allow users to navigate directly to the relevant page by clicking on each item. Our developers confirmed that both options would require equal implementation effort. Since Option B offered superior user experience, we decided to proceed with the notifications menu approach.
Final Outcome & Results
View Live Prototype
What was shipped
- A new onboarding experience with drastically less steps to take for the user to submit their payment and get access to the term of the payment.
- A notifications menu within terminal loaded with all the tasks the new user needs to complete to properly set up their terminal.
- A new Placement Desk feature enabled upon the start of a new terminal.
The business value
- Conversion Rate:
- Funnel Analysis: Percentage of users that sign up in 60 seconds or less = 0.9% of users YTD
- Funnel Analysis: Percentage of users that got their first quote in 5 minutes or less = 11% of users YTD
- Funnel Analysis: Percentage of Placement Desk completed quotes vs all other quotes = 1.17% of user for pilot 30 days
The user value
- Time to First Quote:
- Show percentage of users who got their first quote within 24 hours = 22.7%
The data supporting the value delivered
Reflection
What worked well
- As a design and product team, we created an excellent solution to our onboarding challenges by removing numerous steps from the first-time wizard and relocating them to individual tasks accessible after terminal launch. The primary goal of effective onboarding is twofold: get users started quickly and implement mechanisms to re-engage those who abandon the process midway.
- A key insight from this project was recognizing our urgent need for a notifications menu. The success of our onboarding redesign ultimately depends on our ability to re-engage users through notifications, push alerts, and email sequences that prompt them to complete important setup actions. This notification system will be essential for properly measuring and quantifying the success of our new approach.
What could be improved
- This was one of my first projects as a design manager, guiding our junior designer who wanted to lead the end-to-end design process. Despite initial hesitation, I mentored them throughout this substantial effort, focusing on reviewing their user flows, wireframes, and mockups at various fidelity levels while providing specific improvement feedback. Another challenge was working with our junior product owner who became overwhelmed managing multiple stakeholders and priorities. I often needed to step in and help make critical decisions to keep the project on schedule. Overall, this proved to be a valuable learning experience.
Marcus White
Home
Bold Penguin
First Time Wizard Agent Onboarding v2
Context
Bold Penguin's core quoting platform (Terminal) enables commercial insurance agents to quickly quote and bind policies from multiple carriers through a single, streamlined digital platform. Bold Penguin is now introducing a new in-house agency—Bold Penguin Placement Desk—that allows agents to get quotes without requiring carrier appointments. This creates an opportunity to reimagine the onboarding experience for new agents, enabling them to take advantage of this new feature immediately upon signing up.
Problem
The current onboarding experience is too lengthy and confusing for new users. This puts additional burden on our customer success teams, who must manually explain the Terminal's capabilities to new agents.
Goal
To streamline agent onboarding and reduce time-to-value in the Bold Penguin Terminal by efficiently guiding new users through account creation, quoting processes, compliance requirements, and commission setup;
- Initial sign-ups should take 60 seconds or less.
- From sign-up to first quote should take 5 minutes or less.
- Compliance approval should take 1 hour or less.
Role
Design Manager
Team:
2 Product Designers
1 Product Owner
1 Director of Product
1 Engineering Team
Timeline:
Q2 2025
Final result preview
View Live Prototype
Discovery
What we started with
- We started with an initial meeting to understand the Bold Penguin Placement Desk and align it with our specific milestone goals for our revamped onboarding efforts.
- The Bold Penguin Placement Desk is a new in-house agency initiative that allows agents to quote and bind policies without requiring carrier appointments. This feature helps agents serve their clients faster, increase agency revenue, streamline policy placement, and enhance operational efficiency.
- The fastest recorded completion time for the current onboarding experience is approximately 2 minutes and 12 seconds.
- Our new goal is to reduce initial sign-up to less than 60 seconds, meaning the agent has created an account and verified their email.
- From sign-up to first quote, we aim to keep the process under five minutes, meaning the agent has successfully submitted their first application form quote.
- We want compliance approval to take less than an hour, meaning the agent has completed all compliance tasks required for commission eligibility.
What was created and the thought process behind it
- We created personas for the types of agents who would enter this new onboarding flow and identified their various starting points.
- We mapped out the different user journeys needed from our current flow:
- A standard flow where the new user signs up first, pays second, and quotes third
- An expedited flow where the new user signs up first, quotes second, and pays third
- A biBERK x Placement Desk flow where agents enter the Terminal for the first time as referrals from biBERK phone agents
What we delivered
- A clear outline for what we needed to design in user flow and low fidelity wireframes for the standard flow and expedited flow.
Initial Design Review
What we started with
- User flows for both the standard flow and the expedited flow, outlining all steps in the onboarding process.
- Lack of clarity about how Bold Penguin Placement Desk would integrate into either of the outlined flows.
What was created and the thought process behind it
- After numerous discussions and feedback sessions, we evaluated the logical sequence for steps within the expedited flow and determined which elements could be eliminated.
- I made the decision to keep only essential steps within the signup portion and move all other steps into the terminal as a checklist for agents to complete at their own pace. The essential steps we decided on were:
- Create your account
- Verify your account
- Create your password
- Tell us about your agency
- Review your subscription
- Enter your payment details
- I advocated for this approach by highlighting best practices from other successful onboarding experiences. I demonstrated how it's standard practice to minimize signup steps—collecting only name, email, and password, followed by plan selection and payment. All remaining setup tasks can then be completed after account creation when users have full access to the platform. This approach significantly streamlines the initial onboarding experience.
What we delivered
- A high-fidelity mockup of the standard flow, outlining all stages of the onboarding experience divided into six key sections:
- Onboarding
- Intercom tour
- Application
- Wholesale submission
- Terminal Checklist tasks
- Bind process
- Through additional discussions, we gained clearer understanding of the Bold Penguin Placement Desk capabilities and how they integrate with the onboarding process. We incorporated this functionality into the mockups, specifically within the wholesale submission and binding process sections.
Feedback Design Review
What we started with
- Through several feedback sessions, I provided critique to our associate product designer on polishing the mockups for presentation to our director of product. Since these were high-fidelity mockups, they needed to be impeccable to effectively highlight our previous discussions. The refined designs clearly helped stakeholders understand the visual elements and copywriting, showing exactly what users would do at each step while setting appropriate expectations.
- We decided to remove the expedited flow to limit the complexity and focus primarily on the standard flow.
What was created and the thought process behind it
- The standard flow has now been revised into five final steps that the agent will be guided through in their first experience diving in the terminal:
- Onboarding: A streamlined process that guides new users through account creation, email verification, agency information collection, plan selection, and payment submission to quickly establish their Bold Penguin Terminal access.
- Intercom Tour: Guides the agent through a concise six-step product tour, highlighting essential navigation elements and key features they'll need on the home dashboard.
- Start First Application & Wholesale Submission: This enables agents to start their first application regardless of carrier appointment status. Upon initial use of the terminal, the Bold Penguin Placement Desk is automatically activated, giving agents immediate access to specific carriers through wholesale channels.
- Terminal Setup Tasks: My task panel on the home dashboard, which guides to a task page outlining all of the outstanding things that the agent needs to do, the properly set up their terminal for the principal as well as producer agents.
- Terminal Setup Complete: We want to define success when the agent has completed all of their terminal set of tasks and received their first application quote, bound the policy and received the commission as a best case scenario
- By creating the terminal setup task page, we developed a solution to address what made the previous onboarding experience so lengthy. This page served as a practical workaround that eliminated the need to build an entirely new notifications menu—a feature we internally recognized as necessary but beyond the scope of this project.
What we delivered
- A design prototype to gather stakeholder feedback for fine-tuning before developer handoff. We prioritized the task sequence on the terminal setup page and refined the copywriting for carrier appointments. Our focus was on clearly communicating to agents what actions needed to be taken and their relative urgency.
- The development team identified an issue with our implementation of new settings pages in the main menu. These pages were separated between tabs anchored by two different settings pages. This created a permissions challenge, as permissions would need to be applied at the tab level rather than the standard page level. After collaboration between design and engineering, we simplified the solution by removing the tabs entirely and making settings pages directly accessible through the menu.
- After meeting with the development team, we presented two options for implementing terminal tasks. Option A involved creating a dedicated terminal task page that would outline all setup requirements. Option B proposed integrating these tasks within a new notifications menu available to all terminal users, which would passively display pending tasks and allow users to navigate directly to the relevant page by clicking on each item. Our developers confirmed that both options would require equal implementation effort. Since Option B offered superior user experience, we decided to proceed with the notifications menu approach.
Final Outcome & Results
View Live Prototype
What was shipped
- A new onboarding experience with drastically less steps to take for the user to submit their payment and get access to the term of the payment.
- A notifications menu within terminal loaded with all the tasks the new user needs to complete to properly set up their terminal.
- A new Placement Desk feature enabled upon the start of a new terminal.
The business value
- Conversion Rate:
- Funnel Analysis: Percentage of users that sign up in 60 seconds or less = 0.9% of users YTD
- Funnel Analysis: Percentage of users that got their first quote in 5 minutes or less = 11% of users YTD
- Funnel Analysis: Percentage of Placement Desk completed quotes vs all other quotes = 1.17% of user for pilot 30 days
The user value
- Time to First Quote:
- Show percentage of users who got their first quote within 24 hours = 22.7%
The data supporting the value delivered
Reflection
What worked well
- As a design and product team, we created an excellent solution to our onboarding challenges by removing numerous steps from the first-time wizard and relocating them to individual tasks accessible after terminal launch. The primary goal of effective onboarding is twofold: get users started quickly and implement mechanisms to re-engage those who abandon the process midway.
- A key insight from this project was recognizing our urgent need for a notifications menu. The success of our onboarding redesign ultimately depends on our ability to re-engage users through notifications, push alerts, and email sequences that prompt them to complete important setup actions. This notification system will be essential for properly measuring and quantifying the success of our new approach.
What could be improved
- This was one of my first projects as a design manager, guiding our junior designer who wanted to lead the end-to-end design process. Despite initial hesitation, I mentored them throughout this substantial effort, focusing on reviewing their user flows, wireframes, and mockups at various fidelity levels while providing specific improvement feedback. Another challenge was working with our junior product owner who became overwhelmed managing multiple stakeholders and priorities. I often needed to step in and help make critical decisions to keep the project on schedule. Overall, this proved to be a valuable learning experience.