Elliott Brown of OnPay Payroll: How To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space

Really ask people how they are. Often people won’t volunteer problems they’re having, and it can be a lot harder to read your team when you’re not together. In one-on-one meetings, make a point of asking your team how they’re doing in a direct and earnest way: Are you getting all the help you need? Are things OK outside of work? Are you enjoying the projects you’re working on?

While questions like these might not need to be asked that often when you can read someone’s face or see how they carry themselves, someone’s emotional state can be hard to read virtually. It might feel uncomfortable to do it, but it helps you quickly get to issues that someone might not volunteer otherwise.


We are living in a new world in which offices are becoming obsolete. How can teams effectively communicate if they are never together? Zoom and Slack are excellent tools, but they don’t replicate all the advantages of being together. What strategies, tools and techniques work to be a highly effective communicator, even if you are not in the same space?

In this interview series, we are interviewing business leaders who share the strategies, tools and techniques they use to effectively and efficiently communicate with their team who may be spread out across the world. As a part of this series, I had the pleasure of interviewing Elliott Brown, a veteran startup marketer who currently leads the marketing team at OnPay, an up-and-coming payroll software company.

He joined their Atlanta-based team after honing his marketing chops in stints with Walmart’s digital arm and successful Silicon Valley startups like SurveyMonkey. He still lives in San Francisco, but manages a team of five marketers from the other side of the country, and plans to expand the team to keep up with OnPay’s growth.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Myroad is an especially long and winding one. I started my career as a practicing attorney, but after a few years, I realized how important my underutilized creative side was to me. I was really fortunate to be able to rely on my writing skills to transition into work as a copywriter, which sort of evolved into being an early content marketer. As I grew into a leader on the creative side, I started learning other marketing disciplines by working cross functionally.

I guess I’ve always liked mixing things up, and I love seeing how different businesses work. Once I had enough experience to run a marketing organization, I jumped at the opportunity to consult for early stage startups that didn’t have a dedicated marketing function yet. OnPay was my favorite client because they had an amazing product and a refreshing attitude about how to build a business responsibly. After really getting to know the team, I soon realized I didn’t want to be working with anyone else!

I became their first marketing hire, and I’ve been building out and managing the marketing team from across the country for over two years.

Can you share the most interesting story that happened to you since you began your career?

I’d have to say that starting my job at SurveyMonkey was really fascinating. The company was growing explosively, and the marketing team was really small. Everyone from HR to the product team would just show up at your desk asking for help with things. Creating a process and establishing a well-understood set of priorities was really important.

We accomplished it by focusing on performance. What’s going to have the biggest impact? And how will we quantify it? When you have those answers in hand, it’s pretty easy to lay out a plan of action and get everyone to agree to it.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

This is going to sound cheesy, but I love this saying: “Yesterday is history, tomorrow is a mystery, and today is a gift (that’s why they call it the present).”

It can be really hard to stay in the moment when you look forward or back too much. When it comes to things that have passed, it’s good to learn from mistakes or achievements, but you have to move on from them. If you dwell too much, it means you’re not preparing for what’s next. Similarly, tomorrow is super uncertain. You plan for it, certainly, but if you worry too much about how something is going to turn out, it can take you out of doing what’s right today. When push comes to shove, today is really all the time you have. Whether it’s at work, with family, or chasing some other passion, you’ve got to cherish and make the most of it.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Nobody has been more important to my success than my wife. Not even close. She helped me realize that I needed to change careers 15 years ago — that I wasn’t being fulfilled as a lawyer. She encouraged me to do it and stood behind me every step of the way. She’s also been a role model and a mentor, because she’s a kick-butt marketer in her own right!

Ok wonderful. Let’s now shift to the main focus of our interview. The pandemic has changed so many things about the way we behave. One of them of course, is how we work and how we communicate in our work. Many teams have started working remotely. Working remotely can be very different than working with a team that is in front of you. This provides great opportunity but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits of having a team physically together?

Before the pandemic, I worked from home in San Francisco and the rest of the marketing team worked out of our offices in Atlanta. I would travel out there every three or four weeks, and I can say from that experience that there isn’t a true replacement to being together in person.

When you’re together, a lot of communication happens by osmosis. You overhear bits of conversations, you learn what other teams are up to while filling up your coffee, you feel the mood around the office. And when you do need to talk to someone, you can just turn around and ask them something. There’s no barrier to communication unless someone has headphones on.

Being together also makes planning and brainstorming a lot easier. As a Silicon Valley acolyte, I really like my Post It notes and white boards.

On the flip side, can you articulate for our readers a few of the main challenges that arise when a team is not in the same space?

I think the key challenge of working in different places is that communication becomes formalized when you’re not together. You have to make a deliberate effort to do it, so it can’t be reflexive or indirect. I think that means you need to communicate more, for sure, and that you also have to be very specific about what you say. If people leave things ambiguously, it can be hard to be certain everyone’s on the same page.

Fantastic. Here is the main question of our interview. Based on your experience, what can one do to address or redress each of those challenges? What are your “5 Things You Need To Know To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space ? (Please share a story or example for each.)

OK… five things you have to do to be effective:

  1. Get standing meetings in place. In addition to our team meeting, I have standing weekly meetings with each person on my team — two with direct reports — as well as other team leads and cross-functional working groups. We don’t always use all the time we lay out, but making time to put together an agenda and talk keeps us all thinking about each other. For example, I love my weekly meetings with our sales lead. I don’t think we absolutely need them, but I learn a lot more about our clients and he learns a lot more about what’s coming down the pipeline by putting 30 minutes on the calendar each week.
  2. Pick up the phone. When more than three or four Slacks go back and forth on a topic, it means that something needs to be explained more. Don’t hesitate to call people to get to the heard of the matter. Chances are you can figure out more in a five minute conversation than you will in an hour of going back and forth in a Slack channel, a Google Doc comment, or whatever indirect medium you might be using.
  3. Plan cross functionally. To get buy-in across teams, it’s a good idea to include them in your planning. When you’re working remotely, being presented with a quarterly plan just isn’t the same as helping make it. The rationale and details can get lost in a Powerpoint, but if you include others in your planning process, they’ll understand where you’re coming from. Your plans will also benefit from their perspective, and any potential objections can be identified and worked through before you’ve gone too far with an idea.
  4. Keep happy hour alive. When your entire relationship with someone takes place on a laptop, things can start to become transactional. Find fun things to do together once in a while so you can get to know each other better as people. My team gets together for a virtual beer every now and then, and we also get together for loose hackathons to tease out concepts for campaigns.
  5. Really ask people how they are. Often people won’t volunteer problems they’re having, and it can be a lot harder to read your team when you’re not together. In one-on-one meetings, make a point of asking your team how they’re doing in a direct and earnest way: Are you getting all the help you need? Are things OK outside of work? Are you enjoying the projects you’re working on?

While questions like these might not need to be asked that often when you can read someone’s face or see how they carry themselves, someone’s emotional state can be hard to read virtually. It might feel uncomfortable to do it, but it helps you quickly get to issues that someone might not volunteer otherwise.

Has your company experienced communication challenges with your workforce working from home during the pandemic? For example, does your company allow employees to use their own cell phones or do they use the company’s phone lines for work? Can you share any other issues that came up?

Because I worked remotely before the pandemic, my team already had some good practices in place. Company wide, the stay at home order did cause some fire drills as we worked to get all our employees (many of whom had desktop computers) the tools they needed to work from home. It was definitely an adjustment and a logistical challenge, but now that we’re set up, a number of employees are likely to have the option to work remotely at least some of the time going forward.

Let’s zoom in a bit. Many tools have been developed to help teams coordinate and communicate with each other. In your personal experiences which tools have been most effective in helping to replicate the benefits of being together in the same space?

Most of the tools we use probably don’t come as much of a surprise. Slack, Google Docs, and video conferencing do 90% of what we need to work well together.

Brainstorming has probably been the biggest challenge. We’ve used Google Jamboards for our virtual whiteboard sessions. They’re not perfect, but they let us get everything out there and move our virtual sticky notes around with ease. Companywide, we’re also using My Virtual Mission to do a group fitness challenge. It’s been a fun way to stay active and get people together.

If you could design the perfect communication feature or system to help your business, what would it be?

The perfect communication system would let people really collaborate in real time — by letting us share a desktop or workspace. Having a single person driving what’s on the screen really limits what the team can do as a group.

My particular expertise and interest is in Unified Communications. Has the pandemic changed the need or appeal for unified communications technology requirements? Can you explain?

I don’t think the pandemic has changed the necessity or appeal of Unified Communications. It’s always been necessary. What the pandemic has done is make ineffective and inefficient communication more of a pain point. It’s also really elevated the products that do more to get things right. For example, Zoom is far from perfect, but it became clear that it does more than any other service when it comes to video conferencing.

The missing link is something that can bring together the quick comms of something like Slack, the visual element of Zoom, and the intuitive collaboration and project management you get from a tool like Notion. And on top of all that, I think we all need to be conscious to use the technology well by remembering that the people on the other end of the line are also humans who need politeness and empathy.

The technology is rapidly evolving and new tools like VR, AR, and Mixed Reality are being developed to help bring remote teams together in a shared virtual space. Is there any technology coming down the pipeline that excites you?

Augmented reality can probably do more to help people interact in a more human way, for sure, but I think there’s still a basic link missing between systems. When push comes to shove, AR is ultimately an enhanced form of user experience. It could do more to help people who aren’t in the same physical location have human interactions, but the underlying interoperability of different systems still needs to be addressed to make work more effective.

Is there a part of this future vision that concerns you? Can you explain?

I hope we can all keep in mind that improved communication tools are a merely substitute for being together — not a replacement. Before the pandemic, my team had a really fantastic cadence where we’d meet in person for a few days and work through everything we needed to do. We’d also spend time bonding and getting inspired by doing things like going to Atlanta’s awesome modern art museum.

Then we’d go heads down and get stuff done for a few weeks. It was a really nice cycle, and I don’t think we needed to be together all the time to be effective. In fact, that time apart was a key to our productivity. If we were all together in a virtual office all the time, I don’t think that would necessarily make us more effective than if we spend some time on our own.

There needs to be balance between being together and being apart.

So far we have discussed communication within a team. How has the pandemic changed the way you interact and engage your customers? How much of your interactions have moved to digital such as chatbots, messaging apps, phone, or video calls?

OnPay’s payroll and HR software is cloud-based, so 99% of our clients’ interactions were already virtual. However, we did start to realize that there’s a lot more we can do to train our clients on how to make the most of our product.

It started because we had to explain the Payroll Protection Program to the small businesses and accountants we work with. As we started to develop our client training muscle, we realized we could be doing a lot more to help our clients use OnPay more effectively. We ultimately rolled out regular training webinars to bring clients up to speed on the finer points of payroll and HR. It’s been vey well received.

In my experience, one of the trickiest parts of working with a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote team member?

Feedback needs to be prompt and specific, but you should also be very clear about how significant the feedback is.

In terms of promptness, it’s really important to call out any issues you see immediately because it will seem like a bigger deal if you bring it up out of the blue later. It will also keep things from festering.

When you deliver feedback, including specific examples is critical — that way it’s much more actionable and it will be harder for someone to misunderstand or disagree. And if they do disagree, you’ve got something specific to discuss. Finally, I think it’s a good idea to categorize the severity of the feedback. If it’s not a huge deal, say it. If it’s really critical, emphasize how important it. And if it’s something that’s part of a larger pattern, call it out. By giving context around your feedback, it will take the sting off of any little things, and it will make sure that big issues are taken seriously.

Can you give any specific ideas about how to create a sense of camaraderie and team cohesion when you are not physically together?

To keep camaraderie strong, I try to make sure we do things together that are outside of everyone’s traditional roles. That could mean doing something purely social (like the happy hours my team has), or it could mean collaborating on something fun. For example, we had a nice group brainstorm on possible titles for a blog we’re rolling out. In addition to involving everyone in a key strategic initiative, it also gave us a chance to be silly together in a safe way where there was no right or wrong outcome.

Ok wonderful. We are nearly done. Here is our last “meaty” question. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I think we all work better when we’re able to completely turn off our work brains every now and then. For me, I’d love to be the creator of a movement that encourages people to pursue their secondary passions when they’re outside of the office. For example, I still love purely creative pursuits, but I don’t have much time to fit them into my schedule. Others thrive on working out, volunteering, cooking, serving community organizations, and an array of other activities.

If we could all have the support and encouragement to really chase secondary pursuits, I think we’d all be healthier and happier. We’d also contribute a lot more to the world.

How can our readers further follow your work online?

My team at OnPay spends a lot of time and effort thinking about how small businesses can avoid common pitfalls and operate more effectively. Follow us on LinkedIn or Twitter to see some of the guidance what we’re producing — or check out OnPay if you could use online payroll, HR and benefits that are served up with a steady stream expert support.

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success.


About The Interviewer: David Liu is the founder and CEO of Deltapath, an award-winning unified communications company that liberates organizations from the barriers of effective communication. Liu is known for his visionary leadership, organic growth strategies, and future-forward technology. Liu is highly committed to achieving a greater purpose with technology. Liu’s business insights are regularly featured in Forbes, Entrepreneur Magazine, Tech Crunch, and more.

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