How Organizational Health and Culture Drive Unlimited PTO Success

Anna Madill
6 min readJun 23, 2022


As our team at Avenue prepares to head off for our second annual Summer Holiday Week (twice a year we close our virtual office for a Summer Holiday Week and a Winter Holiday Week), it’s a reminder for me to reflect on why I choose to focus relentlessly on creating an environment where everyone is empowered to take a break. Here’s my why: I believe everyone needs downtime to function at a high level during their “on” time. Not just at work, but in their personal lives, too. I’ve also gotten it wrong so many times before, wearing late nights, early mornings and weekends as a badge of honor to “prove my worth,” while burning out without realizing it until other areas of my life were suffering.

Over the years, I’ve come to realize that our clients love working with us because our team members are inspired by the work, passionate about client success and overall committed to long-term growth with, and at, Avenue. When our clients stay with us and grow, Avenue grows and team members grow. And in order for all of those things to happen, team members need to have the safety and cultural permission to take true vacations, unplug and recharge.

Or, as my two-year old puts it, when it’s “out of batteries” it “needs more electrons.” Simple toddler logic. And it applies to humans, too.

Bottom line, Avenue is a more sustainable and profitable company when team members are well-rested. It has a cascading effect on downstream outcomes. When team members are respected for their contributions and empowered by cultural norms that promote their well-being, the healthier they will be. And the better they will be at taking care of our clients, each other and the business, by helping the team and clients realize meaningful business outcomes.

So, now that you’ve heard why we do it, let’s talk about how we tackle Unlimited PTO. I believe its success comes down to two things: (one) organizational health and (two) culture.

Unpopular Opinion: Unlimited PTO works! (it’s all about organizational health and culture)

Unlimited PTO is a controversial topic to raise at happy hour gatherings, business meet-ups and family dinners. Is it good or is it bad? Most folks have an opinion based on their own experience or stories that they’ve heard. The concerns usually start with the red flags and hidden pitfalls of Unlimited PTO. The general gist is, “It looks shiny on the outside, but it’s really not that great.” Those things can be true. Unlimited PTO won’t be set up for success in a culture that doesn’t truly support time off. It can only be as successful as the organizational culture that supports it, which means: (one) a high-trust, healthy organization is essential and, (two) a culture that promotes, measures and rewards taking time off is imperative.

An organizational culture that leads to a successful Unlimited PTO policy starts with leadership. I believe in this so strongly that I created Avenue’s bi-annual Holiday Weeks and Unlimited PTO policy, which I share in my post on The Power of PTO and No Meeting Fridays. When cultural norms create a toxic environment where no one can truly take PTO, it’s probably not going to work. However, a healthy organization that has a culture that helps team members protect their vacation time will promote team retention and all the bells and whistles that come with it. If done correctly, rather than Unlimited PTO being a red flag (for things like no accrued PTO payout, implied that the less PTO you take the more valuable you are as an employee, etc.), it can signal a high-trust, engaged culture.

Here’s what Unlimited PTO looks like at Avenue

Unlimited PTO policies can often feel like an honor system that actually discourages the use of PTO. I believe that by flipping that cultural norm on its head and celebrating and measuring team members’ PTO, Avenue can double down on creating a healthy organization and a culture that supports taking time off. At Avenue, ‘Days of PTO Taken’ is a Key Performance Indicator (KPI) we measure on a monthly basis. The metric is front and center in our scorecard, and hitting our PTO target helps team members earn their collective bonus at the end of the year, too!

To help nurture organizational health and a culture that supports taking time off, here are a few of the things Avenue is doing:

  • Setting clear expectations and boundaries for team members and clients that the team is not available 24/7, which alleviates the sense of urgency to react or respond.
  • Presenting every new client with an onboarding presentation during the partnership kick-off that sets expectations and walks through our philosophy on time off, rest, recharging, no-meeting Fridays, holidays weeks and how those things all benefit their business outcomes and our partnership.
  • Ensuring and reminding team members that working after hours (unless they prefer being a night owl and they flex their hours accordingly) is strongly discouraged.
  • Having leadership and managers modeling early sign-offs at the end of the day and not sending emails or Slack messages before or after hours.
  • And when someone is on PTO, scheduling emails and Slack messages to send to them after their PTO ends, so that even if someone “accidentally” logs on to check messages, they won’t have any!
  • Having leadership and managers transparently debunk the stigma around “butts in seats” as a productivity metric. If a team member’s status goes offline on Slack (because they are running errands, taking a nap, watching TV, meditating, walking around the block, etc.) team members don’t need to explain themselves. You do you. As long as work is getting done and deadlines are being met, schedule breaks and downtime as needed.
  • Team members set an emoji/OOO message on Slack so team members know they’re offline and when to expect them back. No questions asked.
  • Creating a cultural norm around setting and communicating ‘heads down’ time for deep work during the day where all email and Slack notifications are turned off and team members are unavailable.
  • Using 15Five Pulse check-ins on a weekly basis to understand how team members are doing, if they are struggling with work/life balance, etc. and using it as a conversation starter to alleviate or reprioritize work, time off and mental space.
  • Celebrating and asking about team member’s PTO. What did you do? How did it go? I’m envious of that trip. Can I live vicariously through you? Would you recommend that location? Help me plan my next trip!
  • Promoting, measuring and rewarding taking time off by keeping the metric highly visible and revisited on a monthly basis. I know that if our PTO utilization metric is not being hit (or is way below target), something will start failing downstream soon.
  • Making space for feedback on the process and team members’ level of comfort and understanding of current policies, to make sure this priority is recognized by all.
  • Avenue suggests that team members take approximately one week of PTO per quarter, in addition to the two Summer and Winter Holiday weeks mentioned above. In total, Avenue team members should be taking around 30 days+/- of PTO in the course of a year. We also have a minimum threshold for PTO. If team members are not taking at least three weeks of PTO (in addition to the Summer and Winter Holiday Weeks) in a year, we believe we’re falling down on our commitment to supporting our team members’ health and wellness. In total, our team should be taking a minimum of 25 days of PTO each year.

While Avenue’s Unlimited PTO policy has been in place since our inception, it has certainly seen less successful and more successful years. It’s become an art and a science, and a continual work in progress. With our internal data behind us and the tools for continuing to co-create a culture that supports PTO, our clients are happier and our business has become more sustainable and scalable. All this is made possible by a team that is healthy, happy and thriving. Thank you, Unlimited PTO.

Originally published at



Anna Madill

CEO of Avenue, a B Corp digital marketing agency that amplifies the impact growth-minded and purpose-driven companies have in the world.