Q&A: What your small business should know about Juneteenth with Issac Vaughn

Danny Speros, Director of People Ops, Zenefits
Jun 15, 2021

Juneteenth is Saturday, June 19th. Should small business leaders plan to acknowledge and celebrate the holiday, even if they haven’t in the past?

On this episode of POPS!, Zenefits Chief Operating Officer Issac Vaughn joins VP of People Ops Danny Speros for a conversation about what Juneteenth is, how it’s celebrated, and the importance of acknowledging it—even if it makes you feel uncomfortable. You’ll hear how talking about Juneteenth plays into broader DEI efforts and why everyone benefits when small businesses foster inclusive workplaces.

After you listen:

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On this episode, you’ll hear:

  • [01:07-02:42] Meet Issac Vaughn, Zenefits’ Chief Operating Officer
  • [03:00-03:54] What Juneteenth is
  • [04:02-06:05] How people celebrate Juneteenth today
  • [06:06-08:03] The importance of supporting Black-owned businesses in celebration of Juneteenth
  • [08:08-10:49] Why acknowledging Juneteenth is good for business
  • [10:49-12:36] Why inclusion is the glue that holds diversity efforts together
  • [13:07-15:10] The key to acknowledging Juneteenth for the first time: authenticity
  • [15:11-17:29] How HR leaders can get employees involved in Juneteenth
  • [17:30-19:42] The impact of DEI efforts and how it can drive engagement

POPS Star Bio

Issac: Currently the Chief Operating Officer at Zenefits, Issac has more than 20 years of experience representing and working both for and with high-growth technology companies. He is passionate about the mission at Zenefits to level the playing field for the other 99.7% – the small and mid-sized businesses that power our economy, and proud to be part of a turnaround leadership team that makes integrity part of everything they do. Before joining Zenefits, Issac served in various roles at Ooyala, including as general counsel, head of corporate development, and CEO.

Danny: Danny comes from a family of entrepreneurs and spent 8 years running the family construction business including HR, Sales, Operations and Accounting. He understands the joys and challenges of building a business and learned a lot about how to avoid some common pitfalls. This context fuels his passion for working with other small businesses at Zenefits. Today, Danny taps more than 20 years of People Ops and small business leadership in his role as VP of People Ops at Zenefits. This makes him a great guest expert for the podcast, so you’ll hear from him often.  And you might just catch an occasional cameo from his young daughter in the background.


Didi: Welcome to POPS the show that shows you how to shift from human resources, paperwork to people, operation for the new world of work handle by answering one question at a time. To help us answer your question. Here’s Issac Vaughn, Chief Operating Officer, and Danny Speros, VP of People Operations at Zenefits.

Danny: Hello, thanks for joining us, Issac. It’s great to be speaking with you here about Juneteenth and about how small businesses and HR leaders can talk about diversity in their workplaces.

I’d like to have you give a brief introduction about yourself. I’ll do the same here in just a second, and then we can begin our conversation. 

Issac: Danny is great to have this opportunity to speak with you about June teeth and its importance and relevance in the workplace. Today. As far as my background is concerned, I’m the chief operating officer of.

Zenefits. And prior to Zenefits, in my previous operating role, I spent over 15 years in the private practice of law as a partner representing companies like Zenefits. And in interesting in thinking back across my time as a. Lawyer. And even recently as an operator, the, the importance of the diversity, equity and inclusion, and one of the things I will say, just at the top of Juneteenth in all my time, practicing law was something that was never specifically discussed or acknowledged, and DEI was more.

Along the lines of just goals of just hiring people to get them in the door. I say all that, because I think acknowledgement recognition and appreciation is really what is the essence of all of this. And from where I sit today, it’s just great to see companies. Starting to have the conversation, even if they’re uncomfortable, because it does accomplish the most important thing at the outset.

And that is acknowledged either events or people or in the case of June teeth holidays, which I would venture to say, most people in the workplace have little to no appreciation or understanding of which is okay, now that we’re talking about it, but the whole key is going to be, how do we build on it?

Moving forward?

Danny: I think a lot of people became, uh, uh, aware of Juneteenth. And last year I think we saw a pretty dramatic shift, but for people that are just nominally aware of it, or, or maybe are, are just started coming, coming to hear about it. Now, what is Juneteenth? 

Issac: It is a holiday now celebrated on the 19th of June to commemorate the emancipation of enslaved.

People in the us. And it was first celebrated in Texas on this date in 1865. This was the last group of slaves to be made aware of the emancipation proclamation, which actually was in 1862. So in Texas, these slaves were finally made aware. That they were, um, free. And so that was June 19th, 1865. Yep. 

Danny: And I guess after the end of the civil war, that was the last place to hear that the civil war was over.

People were free now. So fast forward a hundred or so years. And tell me a little bit about how, how people celebrate that holiday. 

Issac: Yeah, I think the ethos behind the holiday is it really is designed to highlight and celebrate the dignity. Freedom and contributions made by black Americans in the U S. And so for me, growing up and probably in my late teens, early twenties, where I became increasingly not only aware of, but acknowledging the holiday, oftentimes they’re local events.

I grew up in San Francisco. And so there’s sections of the city. Where you had larger populations of, uh, blacks. And they use the, took on the feel of a street festival, where there would be food and there’d be music. And there would be a local black businesses showing their wares. So for me, it’s always signified, but opportunity to get out into the community.

To some of these local events in some cities and some parts of the city put on bigger celebrations than others, where you may be seeing hundreds of folks and then others it’s much smaller, but yeah, it’s a day of celebration and a dare reflection again on. The many contributions that the black Americans have made to all aspects of American society, including business 

Danny: corporation of a party, but also the recognition and the celebration of the accomplishments.

And then I don’t recall learning about Jean team. In school, don’t recall learning about it early on in my professional career, actually, when my wife and I adopted our child. So our daughter’s black and that was a moment for us to really learn more. So I’m obviously white and my wife’s white, and this was something that if we were going to raise a black child and in America and a white parents, then this is something we needed to get more involved in.

And Juneteenth was one of the first things that, that we got involved in. And yeah, it was great to see. Like the party, but be a celebration of the businesses that are owned and operated by black people here in the community. 

Issac: If you think about it in the context of small businesses, many black. Owned businesses are small businesses.

There are very few that are scaled if you will. And so we know from our own experience at Zenefits, how many small businesses there are in the United States. And we talk about leveling the playing field for the 99.7%. Those are the 6 million businesses in the U S alone with less than 500 employees. So you take those demographics.

Combine it with, I think, increased institutional recognition. Cause you said something which is important, which is two teeth is not at least for a long time. It was not discussed in school. It certainly wasn’t when I was coming up and you’ve said the same thing. And so I think there’s a great opportunity now to raise the collective understanding and appreciation for the holiday, but obviously more importantly, the contributions of black Americans.

And then it also for companies in particular, including ours, gives us an opportunity to. Really know, even more so who our customers are, what’s behind the name and just mathematically, we know a good number of small businesses are going to have owners who are African Americans. And so that gives us a chance to celebrate and acknowledge those contributions real time and current experience by supporting those businesses in ways that companies can.

Supporting one another to advance the efforts. 

Danny: Your points are, you’re talking like for us at Zenefits, our customers, certainly a number of them fall into black owned businesses. And many of our, their employees may also be black employees as well. And. For other companies too, thinking about how we interact with our customers in our communities, this kind of awareness actually helps us do a better job serving their needs.

What are some of the reasons why, why businesses would want to talk 

Issac: about this it’ll sound trite, but it’s also bored out on the data. It’s actually good for their business. When you look at the data and it’s more, uh, Sort of a, a DEI sort of metric, but the bottom line is companies that are advanced on the DEI spectrum.

It’s proven they’re there. They’re more profitable. They grow faster, they attract and retain a broader base, talented base of employees. And some would say, well, what relevance is that in a small business, it’s all relative right at the end of the day. And we also know from our experience at Zenefit today’s employees, whether they work for a big company or small company, they have an expectation about the employer, employee compact and.

This younger generation of employees are much more socially conscious. So I would tell a small business. Leader. I would tell an HR professional of companies of all sizes. It is in your near-term and long-term best interests of your company. If you want to attract talent, if you want to connect further with many of your customers who are women and minority owned businesses.

Having this gene, if you will, or this part of your organization become more and more core to who it is and its values, you’re going to need to do that and ignore it. And you run the risk of potentially without knowing it or admitting to. Alienating large segments of customers who otherwise don’t want to do business with you, employees who won’t give you the time of the day, because they see no commitment whatsoever.

And so while it may sound like a relatively simple exercise, Acknowledging Juneteenth in the workplace, celebrating it, encouraging your employees to first understand why the holiday exists and then look for ways to celebrate or join. The celebration will go a long ways because there are going to be some employees in your company who are going to expect that would be the case.

And when it doesn’t, it’s going to send a message to them and then others are going to shout. In a positive way, proudly that their company acknowledges it, celebrates it, that it’s not something they even had to raise in the first instance. So there’s just so many good reasons. It’s good for business.

It’s good for culture. It’s good. I think for attracting and retaining employees, and I think it also translates depending upon your business and who your customers are, but odds are, it’s going to give you a deeper connection to many of the customers that you’re already serving. 

Danny: Yeah, I think on the people operations side, where I sit at, I’ve watched diversity be such an important thing in the workplace in the last year or so from where I sit, it’s been important to me and to a lot of the professionals that I work with for a long time, but to see the emphasis put on it in the last year or so, but you touched on what I see as the glue.

It’s one thing to attract people to accompany, but if they don’t feel included, if everybody doesn’t feel included in the workspace and you don’t have the glue that essentially holds that diversity together. And so Jean teams can be an incredible opportunity to demonstrate to employees that. This is something we’re open to talking about.

This is something that’s important to us as a company. And we value the people in the contributions from all of the different walks of life that 

Issac: come in here. That’s exactly right. Especially Danny and small companies in particular, where they just have not of a size and scale where they can have a diversified leadership.

They may not even have the leadership team, but they have team is the owner. Exactly. And this is a way, I think you said it well too, to convey to those folks. That you are aware, or as Chris would like, say that you’re woke and you are going to acknowledge this holiday because it celebrates the contributions of black Americans in this country.

And that’s an important thing, irrespective of whether you’re white or Asian or black or Hispanic, it’s just, these are important things. One of our values in it together, that’s in it together. It’s acknowledging and recognizing. Everyone’s contributions and how that plays into our own life experiences and our own personal and business success.

Danny: Black history is American history, the contributions of people across all of the different backgrounds in America, our American history. And to the extent we. May or may not have had the opportunity to learn those things appropriately in school. Like life is one big learning opportunity. And to the extent employers can share in that with their employees.

I think that creates, I don’t know, some stickiness to the employee experience and is attractive to people of all backgrounds 

Issac: agreed. And one maybe final thing. The elephant always in the room is that people are not comfortable talking about it. And that oftentimes. Means it doesn’t get talked about because people are not comfortable.

And my advice on that point in particular is it’s okay. Especially in the beginning that you’re not comfortable and you feel uncomfortable, it still doesn’t mean that people won’t see value in your acknowledging the holiday. Even if you admit it, the one you didn’t know about it growing up, or you weren’t aware of it until recently.

It really comes down to your intentions for it. And if you are intentional and authentic and authentic, doesn’t mean you have known it and have lived it all your life authentic means your natural voice. So your natural voice in the beginning may be, Hey, I wasn’t even aware of it. I should have, but I didn’t.

But now I do. And now that I understand it, I’ll tell you on the other side of that, if I hear that there’s a black person, I’m not hung up on the fact that they’re just now acknowledging it, what I’m really listening to is are they doing it because they feel they have to because that’s, you know what the current thing is, are they doing it because they understand.

What the holiday represents and why that’s important and then are able to translate for themselves what that means to them personally, what it means for their business. So let the awkwardness subside and just embrace the opportunity to bring people together. 

Danny: Yeah, I think that’s great with some topics like this.

Some people do either stay away from it or come at it, knowing everything. And the reality is you don’t have to do that. And if anything is coming at it with the level of vulnerability and authenticity helps everybody else. Come to the table as well, so that nobody feels intimidated by the conversation and the level of the conversation.

It’s important to us when we have, when we have conversations like this within our company and within our teams, that essentially we meet our people where they’re at, and it creates an environment where people are okay, being a little uncomfortable, but not so uncomfortable that they don’t participate.

But what are some ways that leaders, HR leaders can get employees involved? 

Issac: Yeah. So I think that something that every company can do of any size or scale is make it a holiday and in advance of the holiday, remind people that the holidays are approaching and we’re taking this time out for these reasons to celebrate this particular holiday and encourage your employees, then.

To spend that time or part of it going to an event in their community or talking about it with people in their broader narrative. So just see acknowledgement, because I think, again, for me, first, it starts with acknowledgement and recognition and we can build on that and then over time it evolves and it may become such that companies are doing more and more things beyond the holiday to drive it home in the workplace.

I think the other thing too, to make it more. Uh, then just the holiday itself, I think use it as a lightning rod. To do what I would call sort of a DEI assessment. And again, small companies, probably not as relevant as companies have some modicum size and skill meaning. Look at your makeup at all levels of the organization.

And is that reflective of the. Broader world we live in. Is it reflective of the broader customer base that you’re serving take inventory of who your customers are at least have it be top of mind and not something that is in the recesses. All of these things, I think are ways in which you can reinforce.

It really is all about which is recognition that contributions are made by many. And that just sets you up up to embrace the increasingly diverse workforce that we have ourselves in. But at least we’re more informed. About many of the people that are coming through the doors, actually her virtually on a daily basis.

And that’s going to be to everyone’s benefit. Cause you said it, which is we’re going to do better. We’re going to feel better when. We’re acknowledged and we’re included when we know that we actually are part of a community that knows you and values you and has a little more understanding and appreciation for myths, not your specific background, general conditions that affect all Americans.

Good and bad. 

Danny: Yeah. When in some of the inclusion efforts that we’ve done at Zenefits, what we found is people from all different backgrounds, appreciate it. It’s not just the specific group that you’re looking to include. Everybody appreciates the fact that we can learn from each other. We can partner with each other and that they see that this is a company that does these kinds of things.

And if they do it for one group, they’ll do it for other groups. And in fact, everybody can. Be more involved in that sense. So yeah, the impact goes well beyond any one specific group and ends up helping. And we’ve seen, there’s a number of statistics out there around employees want to work for companies that take this kind of approach and more and more, and increasingly younger generations are actually demanding it, which is.

Fun and exciting to see. Yeah. So it, it creates some additional opportunities beyond just the goodness and the appropriate response to these 

Issac: kinds of things. Yeah. And we know that not all cultures are the same and if you build a really healthy. You know, culture where everyone for the most part feels included.

There’s always going to be people no matter what that won’t, but that can become a barrier and a switch switching costs. So we also know that in the workplace yeah. How much I get paid and what are my opportunities for advancement or are important, but who you work with and under what conditions, and also plays into it as well.

And so at the margins, it makes a huge difference and sometimes. It can make a material difference, meaning people will stay versus just. Take another opportunity cause it’s significantly more money now. Of course, there’s a whole bunch that goes into that and everyone’s at a different place in their life where they can make those decisions.

And I’m not making the point around retention as much as I am. There’s more good. That’s going to come then downside by investing in the kinds of things that drive inclusivity. Because I think that also helps drive engagement and engagement drives actual. Results that matter in the business context, across every key performance indicator you can think of.

Danny: Yeah. And it’s free. I got to do is talk about it, talk about it. These are easy things we can do. And I know a few 19 falls on a Saturday this year. So I, I expect that as the pandemic restrictions are being lifted in various levels across the U S I assume there’ll be some good parties out there to the extent that any one particular neck of the woods doesn’t necessarily have that there’s all kinds of neat stuff that can be done virtually and some learning opportunities out 

Issac: there.

A hundred percent. I will actually be at a party on June 19th, except this will be a wedding for the daughter of a good friend, but otherwise I will be celebrating. And I know the people in that room, we will have a good time. Right on. 

Danny: And what kind of a neat thing to be able to celebrate their anniversary on June 19th, every year from a hundred percent 

Issac: here on 

Danny: out a hundred percent.

That’s a, that’s a neat thing. Yep. All right. Well, um, thank you Issac, for taking this time to talk with us, and I hope you enjoy that wedding. And I appreciate truly from the bottom of my heart, the work that you do for us here at Zenefits, in your professional capacity and beer outside capacity, and helping us come together and rally around the important things in life.

Issac: I appreciate your thoughts. They humble me and I too enjoy working with you and others at a place where it was just collection of find individuals doing good stuff for all the right reasons, but it’s a lot easier to tackle our problems when I get the shoulder up with people like you.

So thank you very much, really enjoyed having the opportunity to talk about. So thank you.

Didi: Do you have a question for our experts? Click the link in the show notes, or if you’ve got other ideas and feedback about our show, send them to [email protected] .


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