About This Episode
In this episode of Reimagining Company Culture, we’re chatting with Jessica Swank, Chief People Officer at Box. Jessica is passionate about creating compelling cultures that enable employees and organizations to thrive, and where employees feel welcomed and celebrated for who they are. Jessica is an advocate of sustainable growth that gives back; for making the communities we live and work in better together. Tune in to learn Jessica’s thoughts on philosophy around training and providing resources to new managers, company community commitments, redesigning internal systems, and more!
About The Guest
Jessica (she/her/hers) has a proven track record helping companies define and amplify their people and culture strategy (including diversity, talent development, employee experience, workforce planning, people analytics, and internal communications). She has been with Box since December 2018, and currently leads all People (HR), Belonging, Community (including Box.org), Places (workplace services and real estate), and Internal Communications. Prior to Box she led the People team at Blue Bottle Coffee, a high-growth third-wave global coffee company. Previously, Jessica led HR for Aruba, a fast-growing subsidiary of HPE, and spent ten years at HP/HPE in a variety of global HR roles. Her early career included executive search and recruiting for CEO's, CFO's and other key leadership positions. Jessica is passionate about creating compelling cultures that enable employees and organizations to thrive, and where employees feel welcomed and celebrated for who they are. Jessica is an advocate of sustainable growth that gives back; for making the communities we live and work in better together.
Episode Breakdown

On this episode of Reimagining Company Culture, we sat down with Jessica Swank, Chief People Officer at Box. Jessica leads people, belonging, community, and workplace services at the company, and she has spent her career helping organizations turn culture from a marketing line into a working operating system. Her phrase for the work is bring your blank self to work, and the blank is intentional. Each employee fills it in differently.

The conversation traced what belonging actually requires from a People team, why manager training is the cheapest lever in the entire culture stack, and how Box has redesigned internal systems to keep belonging from breaking under scale. Jessica's point was clear: belonging is not a poster, it is the result of dozens of operational choices that show up in onboarding, manager rituals, and how feedback gets handled when the news is hard.

Why Belonging Has to Be Designed, Not Declared

Belonging is one of the most over-claimed and under-built ideas in modern HR. The slogan is everywhere. The systems behind it are usually thin. Jessica's team approaches belonging as a design problem with measurable inputs: who gets a real onboarding, whose voice is amplified in meetings, whose ideas are credited, who gets the stretch project, who hears tough feedback in time to grow.

The connection to engagement is direct. According to Gallup's reporting on the decline in U.S. engagement, the gap between top and bottom-quartile teams is largely a manager gap. Belonging is the human-experience term for what those top-quartile managers are doing every week. The companies that crack belonging crack engagement, and the companies that fail at one fail at the other.

Building this kind of engagement-first culture requires investment in the manager layer, not just the executive layer. Jessica's view is that the executive declarations only matter if the manager rituals match.

Manager Training as the Belonging Lever

Why is manager training the highest-impact culture investment?

Because the manager is where culture is experienced. An employee can love the company values and still leave because their manager runs a one-on-one badly for six straight months. Investing in management training is how People teams turn declarations into reality.

What does Box do differently with new managers?

The training is structured, scenario-based, and recurrent. New managers do not get a one-time orientation. They get a year-long curriculum with peer coaching, scripts for hard conversations, and a feedback loop with their own managers. That structure is what carries the company's belonging language into actual team behavior.

What Actually Works for Belonging at Scale

Build belonging into onboarding, not just events

The first thirty days set patterns that take years to undo. New hires need to see how feedback is given, how disagreement is handled, and what good looks like. Without that, the offsite belonging events feel like decoration on a foundation that does not exist.

Use community commitments as accountability

Box's community commitments give employees a frame for what the company will do and what they can hold the company to. That accountability is what keeps belonging from being a press cycle.

Redesign internal systems to remove friction

If reporting concerns is hard, employees stop. If giving feedback to a manager is risky, employees stop. Belonging at scale requires employee survey tools and anonymous channels that lower the cost of speaking up.

Where Employee Relations Fits in Belonging-First Cultures

Belonging promises break in the moment a hard case lands. Harassment, discrimination, retaliation, and manager misconduct are all moments where the company's belonging story is tested. The EEOC's enforcement guidance on workplace harassment emphasizes that an effective complaint process is the foundation of legal compliance and culture credibility at the same time.

That is where HR case management belongs in the conversation. A real case management system protects the company legally and protects the belonging story operationally. Without it, the belonging slogan turns into a credibility loss the moment a case is mishandled.

How do ER teams reinforce belonging?

By treating every case with the rigor and respect the slogan promises. Pattern data from a centralized system also tells leaders which teams need targeted coaching to keep the slogan honest.

Frequently Asked Questions About Belonging at Work

What is the difference between belonging and inclusion?

Inclusion is about access. Belonging is about whether that access leads to feeling valued. The two are connected, but a company can be technically inclusive and still leave employees feeling out of place.

How do you measure belonging?

Track sentiment alongside operational metrics like promotion velocity, internal mobility, and case volume by team. Pair the numbers with open-ended employee feedback to see how the data connects to lived experience.

Can belonging scale beyond a small team?

Yes, but only with manager training, intentional onboarding, and feedback systems that catch drift early. Without those, scale dilutes belonging quickly.

What is the role of executive sponsorship in belonging work?

It matters at the start and at moments of crisis. The everyday work belongs to managers. Executive sponsorship provides resources and air cover, not weekly delivery.

What is the biggest mistake CPOs make on belonging?

Treating it as a campaign. Belonging is an operating system, not a launch. Companies that confuse the two run a lot of events without changing how the company actually works.

The Bottom Line for HR Leaders

Jessica Swank's framing of bring your blank self to work works because it is intentionally incomplete. Each employee fills in the blank, which means the People team has to design systems that work across hundreds of different fill-ins. That is harder than a poster, and it is the actual work.

For HR leaders trying to build belonging-first cultures, the practical path is investment in manager training, intentional onboarding, and feedback systems that surface the truth. Pair that with an ER infrastructure that handles hard cases with rigor. Repeat for ten quarters and the slogan starts to match the reality.

SHRM's Global Workplace Culture Report backs the same playbook with data: culture maturity correlates with operational habits, not slogans. Box is one of the cleaner case studies of that pattern in practice.

One detail Jessica returned to was the role of philanthropy and community work in carrying belonging from internal practice to external credibility. Box.org gives employees a clean way to put their values into action, and that connection between work and community closes a loop that pure HR programs struggle to close on their own.

For mid-market and enterprise teams trying to design something similar, the practical move is to build small belonging rituals that compound over time. A weekly check-in habit. A monthly pattern review with managers. A quarterly look at the case data to spot teams under stress. None of that is unusual, and all of it works when it is repeated honestly across enough quarters.

That patient version of the work is what separates companies whose belonging language ages well from companies whose belonging language ages into a punchline. Jessica is building the former, on purpose.

The bottom line is that belonging at scale is built one habit at a time. The companies that make those habits visible end up with employees who can describe the culture in their own words, which is the strongest signal a People team can hope for.

See how AllVoices supports the operational backbone of belonging-first cultures.

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Chief People Officer at Box, Jessica Swank - Bring Your Blank Self to Work
Episode 190
About This Episode
In this episode of Reimagining Company Culture, we’re chatting with Jessica Swank, Chief People Officer at Box. Jessica is passionate about creating compelling cultures that enable employees and organizations to thrive, and where employees feel welcomed and celebrated for who they are. Jessica is an advocate of sustainable growth that gives back; for making the communities we live and work in better together. Tune in to learn Jessica’s thoughts on philosophy around training and providing resources to new managers, company community commitments, redesigning internal systems, and more!
About The Guest
Jessica (she/her/hers) has a proven track record helping companies define and amplify their people and culture strategy (including diversity, talent development, employee experience, workforce planning, people analytics, and internal communications). She has been with Box since December 2018, and currently leads all People (HR), Belonging, Community (including Box.org), Places (workplace services and real estate), and Internal Communications. Prior to Box she led the People team at Blue Bottle Coffee, a high-growth third-wave global coffee company. Previously, Jessica led HR for Aruba, a fast-growing subsidiary of HPE, and spent ten years at HP/HPE in a variety of global HR roles. Her early career included executive search and recruiting for CEO's, CFO's and other key leadership positions. Jessica is passionate about creating compelling cultures that enable employees and organizations to thrive, and where employees feel welcomed and celebrated for who they are. Jessica is an advocate of sustainable growth that gives back; for making the communities we live and work in better together.
Episode Transcription

On this episode of Reimagining Company Culture, we sat down with Jessica Swank, Chief People Officer at Box. Jessica leads people, belonging, community, and workplace services at the company, and she has spent her career helping organizations turn culture from a marketing line into a working operating system. Her phrase for the work is bring your blank self to work, and the blank is intentional. Each employee fills it in differently.

The conversation traced what belonging actually requires from a People team, why manager training is the cheapest lever in the entire culture stack, and how Box has redesigned internal systems to keep belonging from breaking under scale. Jessica's point was clear: belonging is not a poster, it is the result of dozens of operational choices that show up in onboarding, manager rituals, and how feedback gets handled when the news is hard.

Why Belonging Has to Be Designed, Not Declared

Belonging is one of the most over-claimed and under-built ideas in modern HR. The slogan is everywhere. The systems behind it are usually thin. Jessica's team approaches belonging as a design problem with measurable inputs: who gets a real onboarding, whose voice is amplified in meetings, whose ideas are credited, who gets the stretch project, who hears tough feedback in time to grow.

The connection to engagement is direct. According to Gallup's reporting on the decline in U.S. engagement, the gap between top and bottom-quartile teams is largely a manager gap. Belonging is the human-experience term for what those top-quartile managers are doing every week. The companies that crack belonging crack engagement, and the companies that fail at one fail at the other.

Building this kind of engagement-first culture requires investment in the manager layer, not just the executive layer. Jessica's view is that the executive declarations only matter if the manager rituals match.

Manager Training as the Belonging Lever

Why is manager training the highest-impact culture investment?

Because the manager is where culture is experienced. An employee can love the company values and still leave because their manager runs a one-on-one badly for six straight months. Investing in management training is how People teams turn declarations into reality.

What does Box do differently with new managers?

The training is structured, scenario-based, and recurrent. New managers do not get a one-time orientation. They get a year-long curriculum with peer coaching, scripts for hard conversations, and a feedback loop with their own managers. That structure is what carries the company's belonging language into actual team behavior.

What Actually Works for Belonging at Scale

Build belonging into onboarding, not just events

The first thirty days set patterns that take years to undo. New hires need to see how feedback is given, how disagreement is handled, and what good looks like. Without that, the offsite belonging events feel like decoration on a foundation that does not exist.

Use community commitments as accountability

Box's community commitments give employees a frame for what the company will do and what they can hold the company to. That accountability is what keeps belonging from being a press cycle.

Redesign internal systems to remove friction

If reporting concerns is hard, employees stop. If giving feedback to a manager is risky, employees stop. Belonging at scale requires employee survey tools and anonymous channels that lower the cost of speaking up.

Where Employee Relations Fits in Belonging-First Cultures

Belonging promises break in the moment a hard case lands. Harassment, discrimination, retaliation, and manager misconduct are all moments where the company's belonging story is tested. The EEOC's enforcement guidance on workplace harassment emphasizes that an effective complaint process is the foundation of legal compliance and culture credibility at the same time.

That is where HR case management belongs in the conversation. A real case management system protects the company legally and protects the belonging story operationally. Without it, the belonging slogan turns into a credibility loss the moment a case is mishandled.

How do ER teams reinforce belonging?

By treating every case with the rigor and respect the slogan promises. Pattern data from a centralized system also tells leaders which teams need targeted coaching to keep the slogan honest.

Frequently Asked Questions About Belonging at Work

What is the difference between belonging and inclusion?

Inclusion is about access. Belonging is about whether that access leads to feeling valued. The two are connected, but a company can be technically inclusive and still leave employees feeling out of place.

How do you measure belonging?

Track sentiment alongside operational metrics like promotion velocity, internal mobility, and case volume by team. Pair the numbers with open-ended employee feedback to see how the data connects to lived experience.

Can belonging scale beyond a small team?

Yes, but only with manager training, intentional onboarding, and feedback systems that catch drift early. Without those, scale dilutes belonging quickly.

What is the role of executive sponsorship in belonging work?

It matters at the start and at moments of crisis. The everyday work belongs to managers. Executive sponsorship provides resources and air cover, not weekly delivery.

What is the biggest mistake CPOs make on belonging?

Treating it as a campaign. Belonging is an operating system, not a launch. Companies that confuse the two run a lot of events without changing how the company actually works.

The Bottom Line for HR Leaders

Jessica Swank's framing of bring your blank self to work works because it is intentionally incomplete. Each employee fills in the blank, which means the People team has to design systems that work across hundreds of different fill-ins. That is harder than a poster, and it is the actual work.

For HR leaders trying to build belonging-first cultures, the practical path is investment in manager training, intentional onboarding, and feedback systems that surface the truth. Pair that with an ER infrastructure that handles hard cases with rigor. Repeat for ten quarters and the slogan starts to match the reality.

SHRM's Global Workplace Culture Report backs the same playbook with data: culture maturity correlates with operational habits, not slogans. Box is one of the cleaner case studies of that pattern in practice.

One detail Jessica returned to was the role of philanthropy and community work in carrying belonging from internal practice to external credibility. Box.org gives employees a clean way to put their values into action, and that connection between work and community closes a loop that pure HR programs struggle to close on their own.

For mid-market and enterprise teams trying to design something similar, the practical move is to build small belonging rituals that compound over time. A weekly check-in habit. A monthly pattern review with managers. A quarterly look at the case data to spot teams under stress. None of that is unusual, and all of it works when it is repeated honestly across enough quarters.

That patient version of the work is what separates companies whose belonging language ages well from companies whose belonging language ages into a punchline. Jessica is building the former, on purpose.

The bottom line is that belonging at scale is built one habit at a time. The companies that make those habits visible end up with employees who can describe the culture in their own words, which is the strongest signal a People team can hope for.

See how AllVoices supports the operational backbone of belonging-first cultures.

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