Key Results
Financial wellness is positioned as a core pillar of Roofstock’s benefits strategy
Strong employee engagement, especially around equity education webinars
Reduced the time People Operations spent fielding complex finance and equity questions by referring employees to Addition Wealth
Employees see the benefit as approachable and easy to use, supporting them across a wide range of financial decisions
Roofstock is a real estate and technology company on a mission to reinvent the rental housing ecosystem. With approximately 600 employees, the company operates across more than 25 states, with large concentrations in markets like Dallas, Birmingham, Atlanta, the Carolinas, and the Midwest. Corporate roles are anchored at the Oakland, California headquarters, but the majority of employees work remotely or in the field.
Summary
As Roofstock scaled and expanded its business through acquisitions, the company recognized that financial wellness needed to be a core pillar of its total rewards strategy. Employees had questions around equity compensation, taxes, retirement planning, and major life decisions – all topics that are deeply personal and often difficult for HR teams to address directly.
To support employees more holistically, while reducing the burden of complex financial questions for the People Operations team, Roofstock partnered with Addition Wealth. Through approachable financial education, equity-focused webinars, tax filing support, and one-on-one access to financial professionals, Addition Wealth helps Roofstock employees make more confident financial decisions and better understand the full value of their compensation and benefits.
The partnership reinforces Roofstock’s people-first philosophy, providing employees with trusted, human guidance at critical moments while enabling the People team to scale support across a distributed workforce.
Roofstock’s People Team Philosophy: Supporting the Whole Person
Roofstock’s benefits strategy is designed around the employee experience, and goes beyond traditional coverage categories. With a distributed, hybrid workforce spanning corporate, remote, and field-based roles, the People Operations team focuses on benefits that support employees both inside and outside of work.
“We really want to look at the whole person,” said Joshua Blackwell, Senior Manager of People Operations at Roofstock. “What makes someone happy, healthy, and wealthy, and how we can support that across all facets of their life.”
That holistic philosophy guides how Roofstock evaluates benefits partners, prioritizing programs that are approachable, relevant across life stages, and scalable for a geographically diverse workforce.
Going Beyond Traditional Benefits
Because Roofstock operates at the intersection of real estate, investing, and technology, the company is able to design benefits that reflect its business and culture.
For example, they offer a travel benefit tied to Roofstock’s short-term rental portfolio, which allows employees to stay at company properties in exchange for feedback on their experience.
“At the end of the day, it’s saying, ‘Go take a vacation on us,’” Blackwell said. “It’s about giving people space to recalibrate.”
The benefit supports employee well-being while also strengthening connection to Roofstock’s evolving product portfolio, reinforcing a people-first culture that aligns benefits with the company’s mission.
Making Financial Wellness a Core Pillar
For Roofstock, financial wellness is not an add-on. It is foundational to overall employee well-being.
“Financial health is inseparable from overall well-being,” said Blackwell. “You can’t have one without the other.”
Roofstock’s workforce spans a wide range of roles, income levels, and life stages. Employees may be navigating equity compensation for the first time, planning for retirement, buying a home, or trying to better understand their benefits and pay.
“We have people from all walks of life,” Blackwell explained. “There are a lot of different, very real financial needs across the company.”
Why Roofstock Chose Addition Wealth
When Blackwell joined Roofstock through an acquisition, Addition Wealth was already part of the benefits package - and the experience left a strong impression.
“The Addition Wealth team was incredibly proactive,” Blackwell said. “They made sure benefit continuity stayed in place and that employees understood what the benefit actually was.”
Addition Wealth stood out for its hands-on onboarding, consistent education, and human approach. “With Addition, I don’t feel like I’m talking to corporate heads,” Blackwell added. “I feel like I’m talking to people who genuinely care about employee wellness.”
That partnership mindset has been key for the People Operations team supporting a large, distributed population.
Employee Engagement: Equity Education and Tax Support
One of the strongest signals of success has been engagement with equity education. While equity is a meaningful part of compensation, it is often complex and difficult for employees to fully understand.
Roofstock partnered closely with Addition Wealth to host multiple equity-focused webinars, which consistently saw strong attendance and positive feedback. By creating a low-pressure environment for employees to ask questions, the sessions helped make complex topics more approachable and actionable.
As part of Addition Wealth’s business practice, the Customer Success team provides clients with communications materials to drive awareness and education to the financial wellness platform. The toolkits include things like flyers, emails, and Slack messages to share with the team.
Tax filing support, for example, has also generated strong interest, after Roofstock amplified the rollout using communication resources provided by Addition Wealth.
“I’ve had a lot of people reach out excited to learn they could take advantage of this support,” Blackwell said. “They’re genuinely eager to use it.”
For the People Operations team, that level of engagement reflects both thoughtful internal promotion and the strength of the partnership.
Supporting HR by Reducing Financial Complexity
Many employee questions that land with HR have financial implications, even when they are not framed that way. Questions about equity, tax implications of role changes, retirement planning, or compensation structure often require time-consuming follow up from People teams who are not financial advisors.
Blackwell encourages HR leaders to look closely at their ticketing systems and identify how many requests ultimately tie back to money, equity, or long term planning. Redirecting even a portion of those inquiries to financial experts can free up significant time for HR teams to focus on strategic initiatives rather than complex, high-touch financial explanations.
Addition Wealth fills that gap by giving employees direct access to credentialed financial professionals, reducing the volume of nuanced, time intensive questions that would otherwise land with the People team.
“It’s a great resource for me as a leader,” said Blackwell. “It helps me support employees more effectively.”
An Approachable, Human Experience
Beyond content and expertise, approachability has been critical to adoption. Financial topics can feel intimidating, and Roofstock wanted a benefit employees would actually use.
“It’s not intimidating,” Blackwell said. “It’s warm, human, and easy to navigate.”
That ease of use, combined with personalized education and one-on-one support, has helped make financial wellness feel accessible across Roofstock’s diverse workforce.
Financial wellness at Roofstock is not a one-time initiative. It is part of a broader, long-term commitment to supporting employees through everyday decisions and complex life moments.
“I really believe this work is impacting people’s lives,” said Blackwell. “And that matters.”
"I attend all of your webinars, they are so helpful."
"You can book time the next day. I think having that reassurance is very calming and good - especially if I have a burning question. I can book someone the next day and they can help me answer the question.”
Key Results
Financial wellness is positioned as a core pillar of Roofstock’s benefits strategy
Strong employee engagement, especially around equity education webinars
Reduced the time People Operations spent fielding complex finance and equity questions by referring employees to Addition Wealth
Employees see the benefit as approachable and easy to use, supporting them across a wide range of financial decisions
Roofstock is a real estate and technology company on a mission to reinvent the rental housing ecosystem. With approximately 600 employees, the company operates across more than 25 states, with large concentrations in markets like Dallas, Birmingham, Atlanta, the Carolinas, and the Midwest. Corporate roles are anchored at the Oakland, California headquarters, but the majority of employees work remotely or in the field.
Summary
As Roofstock scaled and expanded its business through acquisitions, the company recognized that financial wellness needed to be a core pillar of its total rewards strategy. Employees had questions around equity compensation, taxes, retirement planning, and major life decisions – all topics that are deeply personal and often difficult for HR teams to address directly.
To support employees more holistically, while reducing the burden of complex financial questions for the People Operations team, Roofstock partnered with Addition Wealth. Through approachable financial education, equity-focused webinars, tax filing support, and one-on-one access to financial professionals, Addition Wealth helps Roofstock employees make more confident financial decisions and better understand the full value of their compensation and benefits.
The partnership reinforces Roofstock’s people-first philosophy, providing employees with trusted, human guidance at critical moments while enabling the People team to scale support across a distributed workforce.
Roofstock’s People Team Philosophy: Supporting the Whole Person
Roofstock’s benefits strategy is designed around the employee experience, and goes beyond traditional coverage categories. With a distributed, hybrid workforce spanning corporate, remote, and field-based roles, the People Operations team focuses on benefits that support employees both inside and outside of work.
“We really want to look at the whole person,” said Joshua Blackwell, Senior Manager of People Operations at Roofstock. “What makes someone happy, healthy, and wealthy, and how we can support that across all facets of their life.”
That holistic philosophy guides how Roofstock evaluates benefits partners, prioritizing programs that are approachable, relevant across life stages, and scalable for a geographically diverse workforce.
Going Beyond Traditional Benefits
Because Roofstock operates at the intersection of real estate, investing, and technology, the company is able to design benefits that reflect its business and culture.
For example, they offer a travel benefit tied to Roofstock’s short-term rental portfolio, which allows employees to stay at company properties in exchange for feedback on their experience.
“At the end of the day, it’s saying, ‘Go take a vacation on us,’” Blackwell said. “It’s about giving people space to recalibrate.”
The benefit supports employee well-being while also strengthening connection to Roofstock’s evolving product portfolio, reinforcing a people-first culture that aligns benefits with the company’s mission.
Making Financial Wellness a Core Pillar
For Roofstock, financial wellness is not an add-on. It is foundational to overall employee well-being.
“Financial health is inseparable from overall well-being,” said Blackwell. “You can’t have one without the other.”
Roofstock’s workforce spans a wide range of roles, income levels, and life stages. Employees may be navigating equity compensation for the first time, planning for retirement, buying a home, or trying to better understand their benefits and pay.
“We have people from all walks of life,” Blackwell explained. “There are a lot of different, very real financial needs across the company.”
Why Roofstock Chose Addition Wealth
When Blackwell joined Roofstock through an acquisition, Addition Wealth was already part of the benefits package - and the experience left a strong impression.
“The Addition Wealth team was incredibly proactive,” Blackwell said. “They made sure benefit continuity stayed in place and that employees understood what the benefit actually was.”
Addition Wealth stood out for its hands-on onboarding, consistent education, and human approach. “With Addition, I don’t feel like I’m talking to corporate heads,” Blackwell added. “I feel like I’m talking to people who genuinely care about employee wellness.”
That partnership mindset has been key for the People Operations team supporting a large, distributed population.
Employee Engagement: Equity Education and Tax Support
One of the strongest signals of success has been engagement with equity education. While equity is a meaningful part of compensation, it is often complex and difficult for employees to fully understand.
Roofstock partnered closely with Addition Wealth to host multiple equity-focused webinars, which consistently saw strong attendance and positive feedback. By creating a low-pressure environment for employees to ask questions, the sessions helped make complex topics more approachable and actionable.
As part of Addition Wealth’s business practice, the Customer Success team provides clients with communications materials to drive awareness and education to the financial wellness platform. The toolkits include things like flyers, emails, and Slack messages to share with the team.
Tax filing support, for example, has also generated strong interest, after Roofstock amplified the rollout using communication resources provided by Addition Wealth.
“I’ve had a lot of people reach out excited to learn they could take advantage of this support,” Blackwell said. “They’re genuinely eager to use it.”
For the People Operations team, that level of engagement reflects both thoughtful internal promotion and the strength of the partnership.
Supporting HR by Reducing Financial Complexity
Many employee questions that land with HR have financial implications, even when they are not framed that way. Questions about equity, tax implications of role changes, retirement planning, or compensation structure often require time-consuming follow up from People teams who are not financial advisors.
Blackwell encourages HR leaders to look closely at their ticketing systems and identify how many requests ultimately tie back to money, equity, or long term planning. Redirecting even a portion of those inquiries to financial experts can free up significant time for HR teams to focus on strategic initiatives rather than complex, high-touch financial explanations.
Addition Wealth fills that gap by giving employees direct access to credentialed financial professionals, reducing the volume of nuanced, time intensive questions that would otherwise land with the People team.
“It’s a great resource for me as a leader,” said Blackwell. “It helps me support employees more effectively.”
An Approachable, Human Experience
Beyond content and expertise, approachability has been critical to adoption. Financial topics can feel intimidating, and Roofstock wanted a benefit employees would actually use.
“It’s not intimidating,” Blackwell said. “It’s warm, human, and easy to navigate.”
That ease of use, combined with personalized education and one-on-one support, has helped make financial wellness feel accessible across Roofstock’s diverse workforce.
Financial wellness at Roofstock is not a one-time initiative. It is part of a broader, long-term commitment to supporting employees through everyday decisions and complex life moments.
“I really believe this work is impacting people’s lives,” said Blackwell. “And that matters.”
"I attend all of your webinars, they are so helpful."
"You can book time the next day. I think having that reassurance is very calming and good - especially if I have a burning question. I can book someone the next day and they can help me answer the question.”
