Episode 367: A Head for Business and a Heart for People With Cindy Strong, VP of People for Outdoorsy

HR in beta has such a ring of truth. When I think about pre-COVID, there was such confidence in HR resources. You could, you can almost close your eyes and imagine, like you’re reading a headline, you know, all the, the podcast and research and reference materials almost said, here’s the next big move for HR. Get all your answers here. And then the global pandemic challenged all of us. We were asked questions, what does employee well-being mean in a setting of social unrest, force, distributed workforce, school closings and concerns of just our physical health? And what is the role of culture and engagement in this environment and how do we recover?

Episode 367: A Head for Business and a Heart for People With Cindy Strong, VP of People for Outdoorsy


Welcome to the Workology Podcast, a podcast for the disruptive workplace leader. Join host Jessica Miller-Merrell, founder of Workology.com as she sits down and gets to the bottom of trends, tools, and case studies for the business leader, HR, and recruiting professional who is tired of the status quo. Now, here’s Jessica with this episode of Workology.

Jessica Miller-Merrell: [00:01:15.43] Welcome to the Workology Podcast, powered by Ace The HR Exam and Upskill HR. These are two of the courses I offer for certification prep and recertification and personal development for HR leaders. This podcast is part of a series on Workology Podcast that’s focused on the roles and responsibilities of the Chief Human Resources Officer or CHRO. The CHRO is sometimes called the SVP of HR or the Chief People Officer, and this role is an executive or C-level role that deals with managing human resources, as well as with organizational development and implementing policies of change to improve the overall efficiency of the company. The CHRO Podcast series on Workology is sponsored by HR Benchmark Survey. Share your insights at HRBenchmarkSurvey.com. Now, one of the reasons I have wanted to do this series and we continue to do this series is because there’s a lot of mystery around that Chief HR Officer level role. I want aspiring heads of HR to know the type of skills and experiences they need to promote into this role, as well as hearing from other HR leaders about things that are working on, points of view, and how they’re partnering and collaborating with their executive peers.

Jessica Miller-Merrell: [00:02:32.56] Before I introduce our podcast guests, I want to hear from you. I would ask, I would love, if you would text “PODCAST” to 512-548-3005. That’s 512-548-3005. You can ask me questions, leave comments, and make suggestions for future guests. This is my community text number. It’s really me and I want to hear from you.

Jessica Miller-Merrell: [00:02:58.30] Today, I’m joined by Cindy Strong. She’s the Vice President of People for Outdoorsy. Cindy is a human resource leader with nearly 20 years of experience in HR, specializing in leadership development, talent management solutions, and training experiences focused on high-performing teams. Outdoorsy is a global online RV rental and outdoor travel marketplace that has been named one of America’s Best Startup Employers in 2022 by Forbes, making the third straight year Outdoorsy has been recognized by Forbes on this exclusive list of the 500 best startup companies to work for in the US. Very cool. I’m so excited to have Cindy on the podcast. Cindy, welcome to the Workology Podcast.

Cindy Strong: [00:03:42.49] Thank you. Thank you for having me.

Jessica Miller-Merrell: [00:03:45.07] Well, let’s start with your background. I wanted to ask how you got your start in HR and how has your work evolved over time into your current role?

Cindy Strong: [00:03:53.41] Yeah, thank you for the question. There is unprecedented interest in HR roles right now, and the journey to it as a career focus is as multidimensional as those that serve the industry in orgs across the globe. Jessica, I’m sure you find it too. It brings together such a unique skill set, experiences, perspectives, education levels that you don’t see in all disciplines. For me, I personally had two primary influencers. First, my mom was an HR professional and a total boss. At an early age, I was able to identify with a successful woman in the workplace, which I believe has served me well throughout my career. Second, I’ve just had this curiosity about lessons and inspiration that come from a group of people. I never saw it as accomplishment of a brand or an org, but rather people coming together to accomplish hard things. The dynamic of synergy and healthy workplaces has always held my attention to answer the second half of your question. My work has evolved through a progressive career like most. What has remained consistent is an application of an operations mindset. I connect dots linking people programs to business imperatives in times of starting any new role or even my season as a consultant. My first question is to leaders and to the org, what’s giving you heartburn? Like what are the gaps in, in our strategic imperatives in accomplishing our strategic imperatives or employee well-being? And then from there, we work to design a roadmap for people operations. There is basic foundational best practices. A lot you share with your audience through Workology that guide us, but it’s not a plug-and-play endeavor there. This strategy must link to the people and to the business.

Jessica Miller-Merrell: [00:05:59.93] I love this and I love that you are like a second-generation HR professional. Especially in an industry that is relatively new. When we look at the history of human resources. Very cool. What skills and experiences do you believe are absolute requirements for that Chief People Officer role? And I want you to think about this maybe in terms of someone who’s just starting out in our industry.

Cindy Strong: [00:06:27.17] Yes, I would encourage them that I don’t think it’s much different than any other senior leader. I believe two primary requirements are a head for business and a heart for people. I’ll give you an example of maybe a head for business and start in my current role. I scheduled 101 meetings until I felt like I had all the answers with the CFO. Asked him to explain the financial reporting. What are our key metrics? What are the market? The threats to the marketplace? What are our opportunities and strengths? This, I could continue to, and then I continue to lean into perspective of functional leaders to round out the people team. And then second, a heart for people to come into focus, a true care and empathy on the well-being for your team. That research is a little different and can take multiple forms. Currently, we are using Lattice for our people’s success platform and we’re midway through that implementation. But so far I’m really excited about the possibilities for us to lean into our teams and where, what their needs might be or where their sentiments are.

Jessica Miller-Merrell: [00:07:37.43] And no lie. Cindy and I were talking before we started recording and we talked about empathy as a leader, and then we also talked about EBITDA. So I feel like your answer covered all the bases for HR professionals. We can’t just be HR experts. We really need to understand the business, but also think about everything we do from that people perspective as well. Another question I wanted to ask. We talked about Outdoorsy being a startup, and so I wanted to have you talk to us about the size of Outdoorsy. What’s the employee size? How big is your team and what does the organizational structure look like in terms of who HR reports to?

Cindy Strong: [00:08:18.02] Sure. We currently have 190 employees. Most are domestic in the US, but we do have team members in Bulgaria, Australia, France, Canada and the UK. So it is a global workforce that we have the opportunity to serve. The current HR team is four and we have an Organizational Development Business Partner, a People Operations Business Partner and a Recruiting Coordinator and Employee that focuses a lot on employee experience. And then my role. In the organization for the way Outdoorsy is structured. We have Outdoorsy Holdings. You mentioned, Jessica, in the beginning of the podcast about the travel brand and that, that’s true to our structure. We have the RV rental workplace, marketplace, and then our insurer tech, Romley. And then future endeavors are also in this structure. Here people, legal, finance, and business unit leaders, we sit at the holdings level and we report to the CEO.

Jessica Miller-Merrell: [00:09:22.57] Interesting. Well, I’m such a nerd. Like, I love to hear and understand where HR sits and how big the team is. And I think it’s really helpful because also there’s not a lot of information out there on employee to HR ratios and what we can expect in the different sectors. So all very helpful information. You joined Outdoorsy in 2021, in the second year of the global pandemic. I can’t believe I’m saying the second year, but here we are. I wanted to ask, what have been your biggest challenges in your first few months on the job?

Cindy Strong: [00:10:01.27] Yeah, first, definitely getting up to speed. And then one of the primary challenges was trying to help co-define with the org the new way of working. Immediately, the leaders, the entire org was asking us to answer big questions. Will we be remote first? Are we going to have a corporate home office? And then have we’ve been successful in adapting to a distributed workforce model? Is this, is this where we’re going to go? The second part, Jessica, was a little healing of the org. I listen to a lot and the effects of abrupt changes, uncertainty, personal stretching could be heard in the feedback from our team members. One of the first responses from the People team in that feedback was offering unlimited mental health support to our team members. In summary and looking at the big, you know, the transactional questions about, about where, where are we going to work and how are we going to work, we just we were very intentional and we remain very intentional about solutions and change management in a group that was pretty fatigued from change, just like every organization across the globe.

Break: [00:11:19.02] Let’s take a reset. My name is Jess Miller-Merrell, and you are listening to the Workology Podcast. It is powered by Ace The HR Exam and Upskill HR. We’re talking about the roles and responsibilities of the Chief Human Resources Officer with my friend Cindy Strong. She’s the VP of People at Outdoorsy. The CHRO podcast series is sponsored by HR Benchmark Survey. Join us. Share your insights. Take our survey at www.HRBenchmarkSurvey.com. Before we go back to the interview, I want to hear from you. Feedback is a gift and I would love for you to text “PODCAST,” the word “PODCAST” to 512-548-3005. That’s 512-548-3005. You can ask questions, leave comments and make suggestions for future podcast guests. This is my community text number and I would love to hear from you.

Break: [00:12:17.57] Benchmarking and data is crucial to HR leaders. Workology’s HR Benchmark Survey is an always-on survey and just by taking the survey at HRBenchmarkSurvey.com, you’re signing up to get comprehensive quarterly results, white papers, and other research from the survey right to your inbox. It takes 10 minutes or less to complete. Visit HRBenchmarkSurvey.com.

HR in Beta: Acting, Testing and Adjusting


Jessica Miller-Merrell: [00:12:44.43] One of the things I love most about working with startups as an HR professional is the ability to kind of start from scratch and be really flexible and nimble. It’s also one of the things I don’t like also, too because you’re always working on something new. But I wanted to ask you about kind of this HR in beta look and ask you how can a test and scale mindset support new HR programs and processes, in your opinion?

Cindy Strong: [00:13:14.49] Wow. HR in beta has such a ring of truth. When I think about pre-COVID, there was such confidence in HR resources. You could, you can almost close your eyes and imagine, like you’re reading a headline, you know, all the, the podcast and research and reference materials almost said, here’s the next big move for HR. Get all your answers here. And then the global pandemic challenged all of us. We were asked questions, what does employee well-being mean in a setting of social unrest, force, distributed workforce, school closings and concerns of just our physical health? And what is the role of culture and engagement in this environment and how do we recover? I don’t think you can find an HR leader that would say that we were they were fully ready for this. But what you can find is thousands that would say, as a profession, we adapted quickly. Information was being shared on every platform. We were learning and educating almost simultaneously as a profession. We all became experts at HR and beta, so to speak. We acted, we tested and we adjusted. We also rose to occasion to lead in places within our organization that had been previously possibly more influenced by other senior leaders like the COO and the CEO. So the muscle of iterating, testing and adjusting that we grew through the pandemic will only serve us as a profession and maybe even more quickly than we anticipated as we now adjust from the great resignation to responding to a recession.

Jessica Miller-Merrell: [00:15:07.19] The R-word. I really hope it’s not, it’s not true.

Cindy Strong: [00:15:10.90] I do.

Jessica Miller-Merrell: [00:15:11.50] I’m in denial. I don’t, I don’t want to believe that it is. Yes, I can get an affordable house, maybe, soon in Austin, but no, not. Not. We’ve been through so much.

Cindy Strong: [00:15:22.46] Yes.

Jessica Miller-Merrell: [00:15:23.57] Can you tell us about change management during a crisis, especially when it comes to communicating with a dispersed workforce?

Cindy Strong: [00:15:32.39] Yes. And I, I now want to geek out on this question because it kind of goes back to that HR and beta, right? As we, I love the trend towards Agile and Scrum certifications in HR that kind of prepared us and are continuing to strengthen us and that HR in beta mode. And in response to your question, so let me answer as a learner and not answer as if the things I’ve learned I got right the first time. And communicating to an intentional or unintentional like happened right after COVID dispersed workforce, I proposed in communication we need a willingness to forge new channels. And then what I, what I’m learning is then you share what they are, and then you share what they are, and including the purpose of them. We lost some of the natural osmosis of information that results out of in-person office settings, and it is different in a dispersed workforce. I heard this definition of communication. I don’t even know how many years and, I reference it so many times. Communication occurs when the receiver understands a message that challenges me, maybe challenges all of us, that we can just throw out data and declare done. So what, how do we build in the communication experience’s feedback that the message was received? And I contend we test success and iterate the way forward.

Cindy Strong: [00:17:11.10] Something that we are learning is there, and we, it’s not like new, there’s lots of studies out there right now. There is a real fatigue from another Zoom meeting. Can we be a little bit brave and have a casual 2 to 3-minute video added to a Slack channel that maybe would accomplish the same? It might be a better experience for our team members. And in that framework, change management in a crisis or any time has a similar foundation. I try to lean into the experience should be felt in a way, maybe even an invitation. It’s something that’s happening with the receiver or the organization and not to them or to it. Very different results. This would include some things that we, some elements that we’ve included in change management, in crisis and in current to help, to help with that is effective communication which we’re all working on to get right. Painting done often. Help people remember where we’re going with the change in the why of the change, and it’s okay to admit what’s still in flux or messy in the change and then making room for stakeholder feedback. This model kind of equalizes the human experience with the requirement of getting the project or the change completed.

Jessica Miller-Merrell: [00:18:41.38] I’m reading a book right now. I just started and I think I’m on the first or second chapter, but it’s by Cal Newport and it’s called Deep Work, and it’s all about the science behind productivity and people who are able to really get things done by eliminating distractions. This is what I’ve gotten so far from the book, but eliminating distractions so that you can really dive into a project or a task or an activity and move very quickly, and really create a product or an end product or end result that is truly heads and shoulders above everyone else. So when you say, Being distracted and always on Zoom calls, I feel like there is a continuation of this kind of crisis mentality that we’re perpetuating in the workplace where we’re just moving from one meeting, one email, one instant message to the other. And we’re not really getting under the surface of following through or making meaningful change in our, in our organization. So I think that setting aside time or resources to talk to each other or to really dive into a problem or communicating with employees in a certain way, I think is, is really incredibly important, especially after what we’ve went through over the last couple of years.

Cindy Strong: [00:20:13.40] Yes, I agree. And I will be ordering that book after this podcast.

Jessica Miller-Merrell: [00:20:18.41] It is, it is so good. Like I sent my team, of course, I should know. But the whole thing is about eliminating distraction. And then I sent a Slack message. It’s like, Hey, everybody, get this book right now. But it’s one of the reasons that I am going to be going on a week-long trip by myself. I’m going to go to Jamaica so I can just focus on me and my business, and really think about what I want to do next. And I am leaving, this, we’re recording this in the beginning of August, but I will be leaving in 11 days from today.

Cindy Strong: [00:20:54.89] Wow, that’s exciting.

Jessica Miller-Merrell: [00:20:57.83] I think it will be. I think we’ll be really good. This book is, is just so awesome. One of the other things I wanted to make sure to ask you is about HR’s role in retention. So employee sentiment has evolved from the pay me on time mindset and I’m using air quotes when I say pay me on time to a, air quotes, contribute to my personal well-being mindset. So we’ve seen the shift and, and that is really, I think making retention such a challenge of our employees. How do you see HR’s role playing out in, in this shift and the focus on retention?

Cindy Strong: [00:21:37.60] Yeah, well this really the theme of HR and beta just is ringing true in our conversation. And obviously, retention is a metric that we use. It’s a good one. And it’s also what the organization and really foundational to that is, will be right to retention. And over the years, recent years, populations and our current workforce have shifted from a need for community, outlets of mission-inspired service or like-minded connection to personal values to the workforce that used to be outside the workforce, but now it is included in the workforce. And that has definitely brought a new element to org, to talent management, to contributing to employee wellbeing. And I think HR’s role is to lead the way. There has been in recent years much talk about creating a seat at the table for HR. Well, friends, your name is on the table tent. This is the place where we can lean into this shift with solutions for our leaders and for our organization and for our team members.

Jessica Miller-Merrell: [00:22:54.40] I love that. And as I’m as you’re talking, I’m thinking. Back in the day, you just worked 40 hours and then you went home and you had other activities that you participated in. And now with kind of the current state in the US, we’re working more, we have more demands than ever before at work. And then of course, if you have kids or other hobbies or activities, so you need to be able to get your well-being and paid in your job because you are exerting so much energy and time at a single place.

Cindy Strong: [00:23:33.40] Yes, very much so.

Jessica Miller-Merrell: [00:23:35.20] Last question for you, is career related. Talk to me about the best career advice you’ve ever received.

Cindy Strong: [00:23:44.34] Yeah. So the best advice actually isn’t something maybe that was spoken to me, but something I observed in HR professionals that I was intentional to mentor me either through what I saw them model or maybe a more formal mentor relationship. And then that is, don’t let previous experiences with HR or sometimes the stigma, stigma of HR define your brand and the success of your people program. Personally, I’ve never experienced an organization to tell me to slow down with smart and effective solutions. It just hasn’t happened, but rather the opposite. Good business leaders want to know the right answers, and they want to do well by people. And I found that to be 99% of the time. And I remember getting my nails done. And you know how people do sometimes in a nail salon and they ask, you know, what do you do? And I said, HR, and she said, you know, nobody likes you. And I said, No, I don’t know that, actually. And that is sometimes what we come with to the table. But don’t let that define you, would be my, the best career advice I’ve received and what I would give.

Jessica Miller-Merrell: [00:25:07.48] So true. I think that people don’t like us because they don’t exactly understand what we do and the full scope or breadth of, of what we’re really involved in, in, in supporting the organization. So it’s a lot of misinformation. I’ve said for a long time that HR has a PR problem.

Cindy Strong: [00:25:25.34] Yeah, I think that’s right. That’s right.

Jessica Miller-Merrell: [00:25:27.82] Well, Cindy, this has been wonderful. Thank you so much for taking time to, to join us. If people wanted to go learn more about Outdoorsy, maybe even apply for any job openings that they, they all might have over there, where would they go to learn more?

Cindy Strong: [00:25:43.72] Yeah. Outdoorsy.com will get you to learn a little bit about our marketplace, our story, the story of our founders, which is amazing and a link to our careers opportunity.

Jessica Miller-Merrell: [00:25:57.88] Awesome. Well, I will also link to the career site on the transcript of the podcast as well as your LinkedIn profile. So if they want to talk shop, they can connect with you there directly too. So thank you again for taking the time. It’s really been a great conversation.

Cindy Strong: [00:26:12.70] Thank you for having me. I really enjoyed this. Thank you, Jessica.

Closing: [00:26:16.43] Thank you so much to Cindy for being a part of the Workology Podcast and our CHRO Podcast series. This series is sponsored by HR Benchmark Survey. Take our survey by going to HRBenchmarkSurvey.com. I love these stories. It’s so interesting. I’m such a nerd in HR. I love hearing about how the role of the Chief Human Resource Officer whose experience connects them to strategy and operations of the overall business. The CHRO doesn’t just lead HR within the company. As Cindy shared, the company depends on this leadership role to set standards and benchmarks for everything from company culture to employee engagement, connection and more. I appreciate Cindy for taking the time to share her experiences with us today.

Closing: [00:27:01.61] I also want to hear from you. Thank you for listening to this podcast and let me know your thoughts, opinions, suggestions. Text the word “PODCAST” to 512-548-3005. That’s 512-548-3005. You can ask me questions, comments and leave suggestions for future guests. It is really me. This is my text number and I want to hear from you.

Closing: [00:27:26.06] I also want to thank you for listening and joining in on the Workology Podcast. It is powered by Upskill HR and Ace The HR Exam. This podcast is a labor of love. It is for you, the disruptive workplace leader who’s tired of the status quo. I’m tired of it. You’re tired of it. Let’s do something to change it. My name is Jessica Miller-Merrell. Until next time, you can visit Workology.com to listen to all our previous Workology Podcast episodes.

Connect with Cindy Strong.



– Cindy Strong on LinkedIn

– Outdoorsy Careers & Employment 

– CHRO Job Description

– Episode 363: Being a Disruptor in HR With Jessica Williams, VP of People at Refine Labs

– Episode 361: CHRO Series – What Skills and Experience Do You Believe Are Absolute Requirements for a CHRO Role?

– Episode 359: Being the Supplement to Communication With John Reeves Whitaker, CHRO at NPH

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Jessica Miller-Merrell

Learn more about Jessica Miller-Merrell, SPHR, SHRM-SCP, the founder of Workology, a workplace HR resource, and the host of the Workology Podcast. More of her blogs can be found here.


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