Mental Well-Being as an Engagement Strategy

What does it cost a business when its people are quietly running on empty? In this episode of CultureClub X, powered by CultureMonkey, host Diana Blass sits down with Jennifer Paxton, co-founder of Jamyr and former VP of People at Smile.io, to unpack how mental wellbeing shapes engagement, productivity and culture, and what HR teams, leaders and managers can actually do about it.

Jennifer brings a decade of experience building and scaling high growth tech startups, including Privy (acquired by Attentive), TrueMotion and Logentries (acquired by Rapid7). She has been part of three successful acquisitions, and almost all of her companies have won best place to work awards at least once while she was there.

Her heart, she says, sits with smaller startups that do not have structure yet and are primed for someone to come in, shape the culture, and build a place employees want to work at and thrive at.

Across the conversation, she and Diana cover the risks of neglecting emotional health, why HR professionals themselves are burning out, the signals managers should watch for, the link between belonging and mental health, and how survey data can surface what employees will not say out loud.

What do organizations risk when they ignore employee mental health?

Jennifer's answer is that everything is connected. Mental health and wellbeing affect every aspect of the business, from an employee's level of productivity to their engagement and collaboration, and even their capacity to think about innovation for the future of the product or the organization.

Culture takes the hit too. When people feel stressed out and unable to take a break, that starts to shape how they communicate with each other and, over time, the overall culture of the organization. In her view, the success of the business ties directly to employees feeling comfortable from a mental health and wellbeing perspective.

The retention stakes are stark. Diana cites World Health Organization research showing that 68% of millennials and 81% of Gen Zers have left roles for mental health reasons. Jennifer adds a data point of her own: she has recently spoken with many HR professionals who are leaving the field, or taking extended breaks, because of their own mental health.

Why are HR professionals burning out, and what do organizations owe them?

Through the pandemic, everyone looked to HR for all of the answers. Jennifer admits she put enormous pressure on herself to have those answers and be perfect all the time, and found it very stressful. Her first fix is structural: organizations should buffer in grace, accept that HR does not have every answer, and develop policies collaboratively so the weight is carried by the entire leadership team.

Her second fix is budget. Asking for resources and being told no again and again leaves HR professionals dissatisfied and almost disincentivized. Real investment means putting money in, and it means the mental health conversation coming from many leaders across the organization, not just from HR.

Where should that budget go? Jennifer points to mental health coverage in the benefits plan, which was an afterthought for years but has risen to the top of what employees ask for. She also flags employee resource groups, going deeper than a one-off yoga session or meditation class, and apps like Spill, which integrates with Slack so employees can connect directly with a therapist.

Her most underrated line item is wellness days, kept separate from PTO rather than lumped in. Tracked on their own, they generate data you can share with teams about how many people take them and what the average is, which normalizes the practice and helps de-stigmatize it.

Leaders who never switch off teach their teams to do the same

Diana raises a theme from earlier episodes this season: employees do not take their PTO, even when it is unlimited. Jennifer's response puts the responsibility on leaders. If you are on vacation but checking email, Slacking people and taking calls, your team sees that behavior and concludes they have to do it too.

The same discipline applies to boundaries on global, asynchronous teams. Sending emails at 10 PM, when a colleague is just waking up, sets expectations nobody agreed to. Delayed send tools can protect the team, though your own wellbeing still needs attention.

Jennifer recalls her own 10 hour days that left her with nothing for her two kids by the evening, a disservice, she says, to the company, to herself and to her wellbeing. Occasional crunches happen, but when they become the norm it is time to model better behavior.

Beyond modeling, she urges leaders to run genuine check-ins from afar: grab 15 minutes on a Slack huddle or Zoom just to see how someone is doing, and have an actual conversation rather than a drive-by greeting. It means a lot, and it carries a lot of weight, when leadership does that.

What signs show a team member is struggling?

Jennifer's first responders are managers who pay attention. On video or in person, watch whether body language has changed from one check-in to the next. When someone answers 'I'm good, it's fine' and shrugs it off, treat it as an opening to ask again: no, really, how are you doing?

Digital signals matter too, because happiness and engagement correlate directly with productivity. Slipping output, going quiet in public channels, or an employee who used to react with emojis on every single post suddenly stopping: these subtle shifts are worth noticing early.

That openness only happens on a deliberate foundation of psychological safety at work, and it comes with accountability: checking in more frequently on someone who is struggling, pointing them to resource groups, apps and benefits, and advocating upward for team-level fixes such as a company-wide mental health day.

At her own company, a manager group and organically formed peer buddies give managers a place to compare notes on what they are seeing and feeling. And Jennifer's famous loose leaf tea ritual sets the stage for one-on-ones: pouring tea keeps her listening instead of talking, and makes her a trusted advisor who controls nobody's salary or progression.

Belonging and mental health are two sides of the same coin

Asked whether a lack of belonging is linked to poor mental health, Jennifer definitely thinks so. When employees feel they have to be performative and cannot bring their whole selves to work, inclusion and belonging suffer. Stigmas persist, access to care is not equal, and cultural norms vary widely: some cultures talk openly about feelings while others are walled off and buttoned up.

Silence shows up at both ends of a career. Newer employees stay quiet because they want to be seen as leaders; senior people feel trapped in a stoic, cookie cutter image and fear being seen differently if they show vulnerability. Providing mental health resources, championing flexibility and modeling vulnerability all help build an inclusive space that is built for all.

The data backs the urgency. Diana points to the same World Health Organization research showing that respondents who say DEI is a mental health issue rose from 41% in 2019 to 54% just a couple of years later.

Can technology really tell you how your people are feeling?

Jennifer distinguishes between two kinds of workplace technology. Resource tools like Spill widen access to therapists. Listening tools factor in how employees are actually feeling and how that changes over time.

A well-designed pulse survey tool shows whether sentiment is up or down through the year and breaks results into segments like relationship with manager, overall happiness and recognition, so you can see which area needs more resources, time and attention.

Her favorite lesson from her own data is the lagging indicator. When something big happened at the company, the survey did not spike that week; it took people about a week to digest it and write in how they really felt. So when you see a spike or a dip, look back a week or two for the cause.

She draws a firm line at employee monitoring tools: not a fan. People crave flexibility and choice, and binary tracking software cannot honor that. Used with good intentions, though, listening tools inform budget allocation and resourcing decisions, even if a tool is never going to solve everything on its own.

Mental wellbeing starts with genuinely listening to employees

Strip away the specifics and one thread runs through this episode: listening. The leader who books 15 minutes just to ask how someone is doing, the manager who notices the missing emojis, the HR team reading pulse survey trends with lagging indicators in mind. Each is a form of paying attention before a struggle becomes a resignation.

Jennifer's parting challenge turns the lens inward: HR people should plot their own survey answers across the year and reflect on how they were feeling, because the profession that listens to everyone else routinely forgets itself.

For organizations, the mandate is the same at scale. Continuous employee listening is what turns mental wellbeing from a poster on the wall into a strategy, and it is the reason platforms like CultureMonkey exist: so people leaders can hear what their employees need and act on it before burnout does the talking.