Designing Employee Experience That Boosts Retention

What actually keeps people at a company? Pay explains part of it, but the daily experience of being trusted, heard, and welcomed explains far more. In this episode of CultureClub X, powered by CultureMonkey, host Diana Blass sits down with Vanesa Cotlar, VP of People and Culture at PolicyMe, to uncover the link between an intentionally crafted employee experience and retention.

Vanesa brings a wide lens to the topic. Before PolicyMe she was Director of People Operations at iQmetrix, a management consultant at Monitor Deloitte Canada, and co-founder and CEO of Octagon Careers, a German-based HR tech startup. She has worked in over 15 countries, holds an MBA from Queen's University, and made the shortlist for Business Leader of the Year at the Women in IT Awards Berlin 2019.

Her current company makes a useful test case. PolicyMe, a digital first life insurance company, has more than tripled its headcount since 2020 to 48 people, with more hiring ahead. Vanesa oversees everything from talent attraction to onboarding, engagement, and career pathing, and her message across the episode is simple: retention is built through intentional choices at every stage of the employee journey.

How can leaders build trust with their direct reports

Vanesa's starting point is ownership. Leaders build trust by giving direct reports real work to run with, not a list of tightly specified tasks to hit. That kind of micromanagement is demotivating, she argues, because it never lets someone take a piece of work from beginning to end and truly make it theirs.

The second ingredient is a climate where experimenting feels safe. Innovation needs comfort with failure, a space where people can ask questions and be wrong without fear, which is the essence of psychological safety at work. When employees feel it is okay to try, and okay if it does not work, trust grows.

The third ingredient reaches beyond work. Vanesa urges leaders to look at the entire person: what they care about, their interests outside the job, and what they want from their careers. Investing in those conversations builds the relationship from both sides, the work and the person.

Career pathing makes growth transparent and equitable

Diana picks up on transparency, and Vanesa describes how PolicyMe turned it into structure. The team built out journeys showing how someone moves from junior designer to head of design, and how the requirements of the role, the autonomy in the work, and the leadership expectations change at every stage.

The payoff comes at self-reflection time. Employees look at their goals to see how far they have come, then look at the career path and objectively assess what they are hitting and what they are still working on. It gives everyone a more equitable framework, even in a startup where only the next 12 to 24 months are truly clear.

What employee experience gaps are quietly driving attrition

Vanesa names three gaps. Lack of trust means every task comes wrapped in second guessing. Lack of flexibility clashes with what research consistently says employees want most. And lack of continuous feedback or recognition strips the fulfillment out of work that occupies such a large share of our lives.

She adds an honest caveat: compensation is still usually the biggest single reason people leave, tied closely to performance reviews and the sense of progression. Experience matters enormously, but pay cannot be waved away.

The remedy starts with diagnosis, because themes are generic and your organization's problems are specific. PolicyMe runs quarterly engagement surveys, holds town halls where anyone can ask questions anonymously or by name, gathers feedback through one-on-ones, and Vanesa herself meets with almost everyone in the company periodically.

Picking one focus makes change memorable and visible. People can see that something has actually been done about the issue the company promised to address.

Is the Gen Z candidate journey really that different

Some things have clearly shifted at the top of the funnel. Younger candidates research employers on TikTok and listen to influencers on what makes a good first job, so the way companies used to market roles is not the way to start those conversations now.

But Vanesa resists the generational stereotype. It is not really a generation thing, she says, it is a listening thing: understanding where the differences are, what candidates are looking for, and how to communicate in a way that makes sense to them and still feels authentic.

For offer drop-off, the moment after signing matters most. Send short videos, mail something to the candidate's home, and take the extra step so they feel welcomed, especially for Gen Zs starting remote first careers without the office relationships earlier generations relied on.

Diana adds a wider point: New York now requires employers to post pay ranges, and salaries are discussed openly on social platforms. Whether the driver is generational or cultural, transparency has become the default expectation.

Where does technology help the employee experience and where does it hurt

Having tried to co-found an HR tech startup herself, Vanesa is blunt about the market: there is so much HR tech out there. Organizations need to be intentional about the where and the why of technology, because five disconnected systems for recognition, reviews, surveys, chat, and video calls make the day to day worse, not better.

Small, well-chosen tools can punch above their weight. PolicyMe has used Donut, a Slack integration that randomly pairs people for coffee chats, and Hypercontext, which builds dynamic meeting agendas in Google Calendar and sends out the notes automatically afterwards.

The line she draws is the human element. An automated Slack prompt asking you to rate your week from one to four is not the same as your manager genuinely asking how your week is going.

Technology also has limits that PolicyMe answers in person. The remote first company gathers everyone three times a year for a lunch, an experiential afternoon like an amazing race through downtown Toronto or treetop trekking, and an optional evening, deliberately modular so nobody with home commitments feels pressure to stay late.

What should happen between the offer and the first day

Companies invest heavily in interviews, then go quiet the moment a candidate signs. That radio silence between signing and starting is where drop-off happens, so PolicyMe treats those weeks as a designed experience, with a checklist called Offer to First Day that assigns clear roles and responsibilities internally.

The touchpoints are simple. Vanesa sends a congratulations email as VP of People, the manager shares excitement and optional reading, and every new hire gets a PM Pal, a buddy from outside their team who is available for a virtual coffee and questions before day one.

Onboarding then keeps the momentum. New hires answer three fun questions from a list and are introduced at town hall, where everyone cheers, a simple and slightly quirky way to spark first conversations and shared experiences.

Culture creates brand advocates when the experience comes first

Vanesa agrees that employees are a company's biggest advocates, but warns against forcing it. The goal is a culture that is authentic and ideally codified, which is why PolicyMe recently recodified its values with clear examples, so incoming hires can quickly understand how the company operates and what it values.

Transparency extends into hiring itself. Near the end of the process, Vanesa runs a back and forth Q&A with candidates to sense check that they truly understand what working at PolicyMe will be like, because not everyone thrives in the same environment.

Her favorite proof point was unplanned. Holiday swag boxes sent to employees' homes, each with identical contents, sparked a weekend of spontaneous thank you photos on Slack. Build experiences people genuinely love, she concludes, and advocacy follows on its own; chase advocacy directly and it rings hollow.

Why continuous listening ties the whole experience together

Strip the episode back and one discipline underpins everything: listening. Career paths answer what employees keep asking about growth. The three attrition gaps only surface if surveys, town halls, and one-on-ones give people a way to name them. Even the Gen Z discussion lands on listening rather than generational labels.

That is the practical takeaway for people leaders. Build a continuous employee feedback loop, act visibly on one thing at a time, and let employees see that speaking up changes something. As Vanesa's work at PolicyMe shows, retention follows the experience, and the experience starts with hearing your people.