Formerly NewRetirement
Turned a powerful retirement engine into a usable, trusted product people would pay for.
I joined as the first dedicated design hire and built design into a trusted growth lever.
Role
Founding Designer → Head of Design & Brand
Time
August 2020 – January 2026 (Remote)
Stage
Seed ($2.2M) → Series A ($30M)
Key Stats
10x conversion rate
20% broader audience
1 → 7 designers
500+ research sessions
8x data adoption
as measured by design team Amplitude usage (compared to other departments)
+6pts NPS
10x conversion rate
20% broader audience
1 → 7 designers
500+ research sessions
8x data adoption
as measured by design team Amplitude usage (compared to other departments)
+6pts NPS
What is Boldin?
Boldin is a DIY financial planning platform that pairs comprehensive software with education, coaching, and advice to help individuals become more financially confident so they can be bold in life.
How Boldin makes money
PlannerPlus subscription
Unlocks all product functionality so customers can complete their financial plan
Coaching sessions
Customers can sit with a financial coach to review their plan for errors and opportunities
Financial advising
Customers can get advice on their plan from a Certified Financial Planner
Enterprise licensing
Companies white label and customize our product for their employees/customers
Starting conditions
What I was up against
An 8-year-old fintech product with heavy UX + UI debt and inconsistent patterns
No dedicated design function (design decisions were fragmented and reactive)
Trust + comprehension were the product (retirement planning is anxiety + numbers + skepticism)
Mobile and modern UX expectations were rising, but the experience lagged
Low conversion baseline (large top-of-funnel, limited paid conversion)
Stakeholder risk-aversion: “don’t change flows unless you can prove it won’t hurt metrics”
Scope of my responsibilities
I led product design + brand evolution across core planning flows, onboarding, dashboards, and lifecycle experiences—shipping measurable improvements to activation, engagement, conversion, and brand perception while scaling a small, scrappy team.
Core UX
onboarding, dashboard, planning flows, editing/management experiences
Brand system
identity evolution, visual language, voice, art direction
Design ops
process, quality bar, cross-functional alignment, team growth
Research
qualitative sessions + quantitative validation and testing
Design system
components, patterns, tokens, governance, quality bar
Marketing design
marketing site, emails, decks, brand templates, social design
Key projects & timeline
September 2020
Redesigned Dashboard
Turned a “wall of metrics” into an at-a-glance, action-driven dashboard in a 2-day sprint—and proved design ROI fast: +12% plan completion and 2x PlannerPlus upgrades.
Engagement rate
12%
Upgrade rate
2x
September 2020
Redesigned Dashboard
Turned a “wall of metrics” into an at-a-glance, action-driven dashboard in a 2-day sprint—and proved design ROI fast: +12% plan completion and 2x PlannerPlus upgrades.
Engagement rate
12%
Upgrade rate
2x
September 2020
Redesigned Dashboard
Turned a “wall of metrics” into an at-a-glance, action-driven dashboard in a 2-day sprint—and proved design ROI fast: +12% plan completion and 2x PlannerPlus upgrades.
Engagement rate
12%
Upgrade rate
2x
September 2020
Redesigned Dashboard
Turned a “wall of metrics” into an at-a-glance, action-driven dashboard in a 2-day sprint—and proved design ROI fast: +12% plan completion and 2x PlannerPlus upgrades.
Engagement rate
12%
Upgrade rate
2x
November 2020
Defining a multiyear vision
In the spirit of getting alignment fast (and not shipping a conflicting design roadmap), I created a multi-year design framework that clarified what to build first, what it unlocks for the business, and how we’d scale the team to deliver it.
November 2020
Defining a multiyear vision
In the spirit of getting alignment fast (and not shipping a conflicting design roadmap), I created a multi-year design framework that clarified what to build first, what it unlocks for the business, and how we’d scale the team to deliver it.
November 2020
Defining a multiyear vision
In the spirit of getting alignment fast (and not shipping a conflicting design roadmap), I created a multi-year design framework that clarified what to build first, what it unlocks for the business, and how we’d scale the team to deliver it.
November 2020
Defining a multiyear vision
In the spirit of getting alignment fast (and not shipping a conflicting design roadmap), I created a multi-year design framework that clarified what to build first, what it unlocks for the business, and how we’d scale the team to deliver it.
December 2020
Redesigned Onboarding
Rebuilt onboarding into a path-based flow that kept completion high while improving monetization—ultimately landing at 86.7% onboarding rate and 4.2% upgrade rate, and becoming the default experience.
Onboarding completion rate
22.8%
Upgrade rate
121%
December 2020
Redesigned Onboarding
Rebuilt onboarding into a path-based flow that kept completion high while improving monetization—ultimately landing at 86.7% onboarding rate and 4.2% upgrade rate, and becoming the default experience.
Onboarding completion rate
22.8%
Upgrade rate
121%
December 2020
Redesigned Onboarding
Rebuilt onboarding into a path-based flow that kept completion high while improving monetization—ultimately landing at 86.7% onboarding rate and 4.2% upgrade rate, and becoming the default experience.
Onboarding completion rate
22.8%
Upgrade rate
121%
December 2020
Redesigned Onboarding
Rebuilt onboarding into a path-based flow that kept completion high while improving monetization—ultimately landing at 86.7% onboarding rate and 4.2% upgrade rate, and becoming the default experience.
Onboarding completion rate
22.8%
Upgrade rate
121%
June 2021
Redesigning data entry & updated navigation
Modernized the “My Plan” guts (navigation + inputs) so people could actually find and finish what mattered—users were 30% faster, hit 100% task success, and subscription rate grew 114%.
All -time Subscription rate
114%
One day subscription rate
67%
June 2021
Redesigning data entry & updated navigation
Modernized the “My Plan” guts (navigation + inputs) so people could actually find and finish what mattered—users were 30% faster, hit 100% task success, and subscription rate grew 114%.
All -time Subscription rate
114%
One day subscription rate
67%
June 2021
Redesigning data entry & updated navigation
Modernized the “My Plan” guts (navigation + inputs) so people could actually find and finish what mattered—users were 30% faster, hit 100% task success, and subscription rate grew 114%.
All -time Subscription rate
114%
One day subscription rate
67%
June 2021
Redesigning data entry & updated navigation
Modernized the “My Plan” guts (navigation + inputs) so people could actually find and finish what mattered—users were 30% faster, hit 100% task success, and subscription rate grew 114%.
All -time Subscription rate
114%
One day subscription rate
67%
September 2022
Brand Phase 1
Led a full brand strategy + identity refresh that made trust tangible—driving 3.5x higher homepage signups and a 4x subscription lift on pricing, plus supporting a $20M Series A pitch deck.
Signup Rate
3X
Subscription Rate
62.5%
NPS
7 pts
September 2022
Brand Phase 1
Led a full brand strategy + identity refresh that made trust tangible—driving 3.5x higher homepage signups and a 4x subscription lift on pricing, plus supporting a $20M Series A pitch deck.
Signup Rate
3X
Subscription Rate
62.5%
NPS
7 pts
September 2022
Brand Phase 1
Led a full brand strategy + identity refresh that made trust tangible—driving 3.5x higher homepage signups and a 4x subscription lift on pricing, plus supporting a $20M Series A pitch deck.
Signup Rate
3X
Subscription Rate
62.5%
NPS
7 pts
September 2022
Brand Phase 1
Led a full brand strategy + identity refresh that made trust tangible—driving 3.5x higher homepage signups and a 4x subscription lift on pricing, plus supporting a $20M Series A pitch deck.
Signup Rate
3X
Subscription Rate
62.5%
NPS
7 pts
December 2022
Scenario Management Redesign
Rebuilt the company’s main retention feature, scenarios, so it felt modern (and monetized): 2x more scenarios created, 10x more upgrades driven from the feature, and 42% of scenario users actively comparing outcomes.
No. Scenarios Created
2X
December 2022
Scenario Management Redesign
Rebuilt the company’s main retention feature, scenarios, so it felt modern (and monetized): 2x more scenarios created, 10x more upgrades driven from the feature, and 42% of scenario users actively comparing outcomes.
No. Scenarios Created
2X
December 2022
Scenario Management Redesign
Rebuilt the company’s main retention feature, scenarios, so it felt modern (and monetized): 2x more scenarios created, 10x more upgrades driven from the feature, and 42% of scenario users actively comparing outcomes.
No. Scenarios Created
2X
December 2022
Scenario Management Redesign
Rebuilt the company’s main retention feature, scenarios, so it felt modern (and monetized): 2x more scenarios created, 10x more upgrades driven from the feature, and 42% of scenario users actively comparing outcomes.
No. Scenarios Created
2X
September 2024
Brand Phase 2
Orchestrated the rename + refresh to broaden the audience—delivering a 20% increase in users under 50, and a 30% conversion lift, while reigniting enterprise interest.
Conversion Rate
30%
Users under age 50
20%
September 2024
Brand Phase 2
Orchestrated the rename + refresh to broaden the audience—delivering a 20% increase in users under 50, and a 30% conversion lift, while reigniting enterprise interest.
Conversion Rate
30%
Users under age 50
20%
September 2024
Brand Phase 2
Orchestrated the rename + refresh to broaden the audience—delivering a 20% increase in users under 50, and a 30% conversion lift, while reigniting enterprise interest.
Conversion Rate
30%
Users under age 50
20%
September 2024
Brand Phase 2
Orchestrated the rename + refresh to broaden the audience—delivering a 20% increase in users under 50, and a 30% conversion lift, while reigniting enterprise interest.
Conversion Rate
30%
Users under age 50
20%
January 2025
Resetting relationships
Replaced “random Slack chaos” with an actual system—rituals, transparency, and a Coda request-to-delivery hub—resulting in 5x design output and dramatically better cross-team collaboration.
Design output
5X
January 2025
Resetting relationships
Replaced “random Slack chaos” with an actual system—rituals, transparency, and a Coda request-to-delivery hub—resulting in 5x design output and dramatically better cross-team collaboration.
Design output
5X
January 2025
Resetting relationships
Replaced “random Slack chaos” with an actual system—rituals, transparency, and a Coda request-to-delivery hub—resulting in 5x design output and dramatically better cross-team collaboration.
Design output
5X
January 2025
Resetting relationships
Replaced “random Slack chaos” with an actual system—rituals, transparency, and a Coda request-to-delivery hub—resulting in 5x design output and dramatically better cross-team collaboration.
Design output
5X
March 2025
Simplifying for the mainstream
After a rough RIF, I helped the team reset with a “Simplification” North Star—19 high-impact initiatives plus a decision framework that got everyone aligned and shipped our first team-owned Q2 roadmap from a 2-day onsite.
March 2025
Simplifying for the mainstream
After a rough RIF, I helped the team reset with a “Simplification” North Star—19 high-impact initiatives plus a decision framework that got everyone aligned and shipped our first team-owned Q2 roadmap from a 2-day onsite.
March 2025
Simplifying for the mainstream
After a rough RIF, I helped the team reset with a “Simplification” North Star—19 high-impact initiatives plus a decision framework that got everyone aligned and shipped our first team-owned Q2 roadmap from a 2-day onsite.
March 2025
Simplifying for the mainstream
After a rough RIF, I helped the team reset with a “Simplification” North Star—19 high-impact initiatives plus a decision framework that got everyone aligned and shipped our first team-owned Q2 roadmap from a 2-day onsite.
April 2025
AI Illustration
Built a branded AI illustration engine that 2x’d social impressions and unlocked faster storytelling—good enough to support partnership pitching (and earn follow-up meetings) with a major bank.
Impressions
2X
April 2025
AI Illustration
Built a branded AI illustration engine that 2x’d social impressions and unlocked faster storytelling—good enough to support partnership pitching (and earn follow-up meetings) with a major bank.
Impressions
2X
April 2025
AI Illustration
Built a branded AI illustration engine that 2x’d social impressions and unlocked faster storytelling—good enough to support partnership pitching (and earn follow-up meetings) with a major bank.
Impressions
2X
April 2025
AI Illustration
Built a branded AI illustration engine that 2x’d social impressions and unlocked faster storytelling—good enough to support partnership pitching (and earn follow-up meetings) with a major bank.
Impressions
2X
May 2025
Welcome Emails
Broke the “don’t touch lifecycle” stalemate with A/B-tested design iteration—lifting welcome click rate 18% (peaking 23% better than the old sequence) and setting a new baseline for lifecycle email.
click rate
18%
May 2025
Welcome Emails
Broke the “don’t touch lifecycle” stalemate with A/B-tested design iteration—lifting welcome click rate 18% (peaking 23% better than the old sequence) and setting a new baseline for lifecycle email.
click rate
18%
May 2025
Welcome Emails
Broke the “don’t touch lifecycle” stalemate with A/B-tested design iteration—lifting welcome click rate 18% (peaking 23% better than the old sequence) and setting a new baseline for lifecycle email.
click rate
18%
May 2025
Welcome Emails
Broke the “don’t touch lifecycle” stalemate with A/B-tested design iteration—lifting welcome click rate 18% (peaking 23% better than the old sequence) and setting a new baseline for lifecycle email.
click rate
18%
September 2025
Integrating AI into our product
Using AI to turn a complex planning experience into clear guidance and driving 41% beta engagement.
September 2025
Integrating AI into our product
Using AI to turn a complex planning experience into clear guidance and driving 41% beta engagement.
September 2025
Integrating AI into our product
Using AI to turn a complex planning experience into clear guidance and driving 41% beta engagement.
September 2025
Integrating AI into our product
Using AI to turn a complex planning experience into clear guidance and driving 41% beta engagement.
Testimonials
Shared with permission
"There isn’t enough time or space to truly document how crucial Rachel is to the success of this business… she is the Boldin glue."
Brooke Peterson
Fmr. Director of Program Management
"As a partner on PDE leadership, Rachel helps drive alignment and resource allocation, which ensures design work is meaningful and immediately actionable by either Product or Engineering."
Brett Stoppel
VP, Engineering
"Rachel has done an amazing job cultivating an environment where design is valued. This means that design is treated as partner. And overall, it’s understood that design and functionality go together."
Cez Corpus
FMR. Senior designer
"Rachel has a strong sense for how our team is doing overall culturally and emotionally, and does a good job of helping us communicate thoughtfully and effectively."
Steve Chen
CEO, Boldin
"Rachel's positive impact to Boldin can't be overstated. She brings institutional knowledge, product/design acumen, an open and inviting communication style and a deeply insightful view of human behavior."
Yun Woo
FMR. Head of Product
"She is objective about the project and balances the business needs with design best practices."
Amanda Erickson
Head of marketing
"She has incredible stakeholder management skills, drives key decisions through the organization and knows how to utilize and delegate to her E and P partners."
Yun Woo
FMR. Head of Product
"There isn’t enough time or space to truly document how crucial Rachel is to the success of this business… she is the Boldin glue."
Brooke Peterson
Fmr. Director of Program Management
"She is objective about the project and balances the business needs with design best practices."
Amanda Erickson
Head of marketing
"Rachel's positive impact to Boldin can't be overstated. She brings institutional knowledge, product/design acumen, an open and inviting communication style and a deeply insightful view of human behavior."
Yun Woo
FMR. Head of Product
"Rachel has done an amazing job cultivating an environment where design is valued. This means that design is treated as partner. And overall, it’s understood that design and functionality go together."
Cez Corpus
FMR. Senior designer
"Rachel has a strong sense for how our team is doing overall culturally and emotionally, and does a good job of helping us communicate thoughtfully and effectively."
Steve Chen
CEO, Boldin
"As a partner on PDE leadership, Rachel helps drive alignment and resource allocation, which ensures design work is meaningful and immediately actionable by either Product or Engineering."
Brett Stoppel
VP, Engineering
"She has incredible stakeholder management skills, drives key decisions through the organization and knows how to utilize and delegate to her E and P partners."
Yun Woo
FMR. Head of Product
"There isn’t enough time or space to truly document how crucial Rachel is to the success of this business… she is the Boldin glue."
Brooke Peterson
Fmr. Director of Program Management
"She is objective about the project and balances the business needs with design best practices."
Amanda Erickson
Head of marketing
"Rachel's positive impact to Boldin can't be overstated. She brings institutional knowledge, product/design acumen, an open and inviting communication style and a deeply insightful view of human behavior."
Yun Woo
FMR. Head of Product
"Rachel has done an amazing job cultivating an environment where design is valued. This means that design is treated as partner. And overall, it’s understood that design and functionality go together."
Cez Corpus
FMR. Senior designer
"Rachel has a strong sense for how our team is doing overall culturally and emotionally, and does a good job of helping us communicate thoughtfully and effectively."
Steve Chen
CEO, Boldin
"As a partner on PDE leadership, Rachel helps drive alignment and resource allocation, which ensures design work is meaningful and immediately actionable by either Product or Engineering."
Brett Stoppel
VP, Engineering
"She has incredible stakeholder management skills, drives key decisions through the organization and knows how to utilize and delegate to her E and P partners."
Yun Woo
FMR. Head of Product
"There isn’t enough time or space to truly document how crucial Rachel is to the success of this business… she is the Boldin glue."
Brooke Peterson
Fmr. Director of Program Management
"Rachel has a strong sense for how our team is doing overall culturally and emotionally, and does a good job of helping us communicate thoughtfully and effectively."
Steve Chen
CEO, Boldin
"She is objective about the project and balances the business needs with design best practices."
Amanda Erickson
Head of marketing
"As a partner on PDE leadership, Rachel helps drive alignment and resource allocation, which ensures design work is meaningful and immediately actionable by either Product or Engineering."
Brett Stoppel
VP, Engineering
"Rachel's positive impact to Boldin can't be overstated. She brings institutional knowledge, product/design acumen, an open and inviting communication style and a deeply insightful view of human behavior."
Yun Woo
FMR. Head of Product
"She has incredible stakeholder management skills, drives key decisions through the organization and knows how to utilize and delegate to her E and P partners."
Yun Woo
FMR. Head of Product
"Rachel has done an amazing job cultivating an environment where design is valued. This means that design is treated as partner. And overall, it’s understood that design and functionality go together."
Cez Corpus
FMR. Senior designer
© 2026 Rachel Diesel
© 2026 Rachel Diesel
© 2026 Rachel Diesel
© 2026 Rachel Diesel