Exclusive Interview with Rich Robert II: Expert Insights on Innovative Marketing Strategies

Rich Robert II, Former Marketing Manager at Justworks, led go-to-market and field marketing initiatives, shaping innovative Marketing Strategies for a company that streamlines HR, payroll, benefits, and compliance solutions. These solutions cater to small and medium-sized businesses. Justworks empowers entrepreneurs by offering big-company benefits through a simple, integrated platform. Consequently, this platform lets business owners focus on growth. Meanwhile, people management runs seamlessly. In this exclusive interview, he shares insights on strategic marketing, integrated campaigns, and customer-centric messaging. These strategies drive measurable success.

Tailoring Justworks Marketing Strategies for SMBs

Mr. Robert, given your extensive experience in account-based marketing, how has Justworks tailored its ABM strategies to engage small and medium-sized businesses effectively?

Rich Robert II: “We had to determine which marketing channels suit small to medium-sized businesses. For example, at enterprise companies, you might use a channel strategy like hosting a luncheon, offering learning sessions, or planning an in-person interactive event. However, with small businesses, you must shift your mindset and adapt your strategy based on their behaviors and influences. Direct mail, for instance, remains a relevant channel for small businesses.

So, we started with email. If email got no response, we then tried direct mail as a secondary option. Why? Because we assume mom-and-pop shops and small businesses still open and review mail. Next, we sent two versions—A/B testing with different copy and creative—to see if they’d scan a QR code. This led them to a unique landing page. There, they could decide to engage further by submitting additional information or requesting an in-person activation.

Ultimately, I devise Marketing Strategies at Justworks that fit small to medium-sized business owners where they are. Certain channels speak to them when others don’t.”

Can you share insights into a recent marketing campaign you spearheaded?

“When I joined, they hired me to build the marketing and go-to-market strategy, plus branding awareness campaigns across Miami and South Florida. The reason? An acquisition enabled us to help small and medium-sized businesses hire globally—a real catapult. So, I took that ethos as a priority. While I can’t highlight one campaign above others, I’ve led multiple efforts, and I’m proud of them.

For instance, I’m thrilled with the team’s work. We started with zero brand awareness. Now, I mention Justworks, and people recognize us—a huge feat. Additionally, we’ve secured partnerships with major league sports teams and mass transit authorities. As a result, our billboards dot the city, and wrapped metro cars with our logos roll through Miami.”

Industry Experience and Audience Engagement

Having held senior marketing roles at Rapyd, Northbeam, and Shopify, what unique perspectives you brought to Justworks?

“I’ve worked in marketing across industries like fashion, entertainment, sports, prop tech, and media buying technology—you name it. Since Justworks targets small to medium-sized businesses, which span many verticals, my varied experience helps. We’re not tied to one industry.

Thus, I offer a fresh outlook on what works across different sectors. Because I’ve tackled so many industries, I bring diverse strategies and perspectives to tailor marketing for Justworks’ broad audience.”

What are the key challenges in marketing HR solutions?

“Marketing for traditional organizations—like HR—that aren’t inherently fun or revenue-focused is tough. For example, take accounting firms or law firms. What’s the common thread? You only seek them when you need them. Founders don’t actively think about law firms or accountants when starting a business. Instead, they focus on revenue-generating tasks.

HR is similar. Imagine you’re a startup founder with a co-founder and a contractor abroad. You don’t initially prioritize payroll or compliance. Yet, these matter when seeking VC funding or building revenue records. You need orderly books, compliant handbooks, and protection from lawsuits—like labor or harassment issues—that could sink a company.

So, marketing HR is hard because people don’t find these topics exciting. They’ve already started their business, using basic payroll or a friend’s accounting referral. As long as costs stay low, they don’t care. Convincing them otherwise is the challenge.”

What metrics do you prioritize when evaluating marketing success?

“In any campaign, metrics depend on the organization’s goals. Right now, as a high-growth company, we emphasize ROI. Marketing, sales, and customer success all tie into revenue. Ideally, these teams align under the revenue organization of any startup.

Thus, we track ARR, ROI, and marketing spend versus returns from marketing-attributed engagement. We can’t fully control sales outcomes, but marketing must give sales the best shot at booking demos. A year ago, though, when I started at Justworks, it was all about brand. Back then, I focused on impressions and unique landing pages to build awareness in Miami.”

Market Trends and the Future of Justworks Marketing

How do you stay ahead of trends in the HR and payroll services industry from a marketing standpoint?

“From a marketing view, it’s all about brand. The challenge? Presenting HR tech in a way that emotionally connects with decision-makers. We must show how it improves payroll, benefits, and culture. Businesses face risks and opportunities, so we use our brand to highlight why HR matters to founders and leaders. Consistently doing this through marketing benefits the HR space.”

Can you glimpse into upcoming Justworks marketing projects or strategies?

“I won’t name a specific campaign, but we’re shifting focus. It’s less about brand now and more about returns. Currently, we’re targeting vertical industries where we’ve historically succeeded. Instead of broad campaigns, we’re doubling down on these core sectors.

Also, we’re leaning heavily into partnership and affiliate marketing. Why? Referrals drive HR product adoption. Small business owners rarely Google ‘HR software.’ Instead, they ask two or three trusted contacts for recommendations. Strengthening our referral network is key.”

Justworks emphasizes supporting minority and women-owned businesses. How have you tailored marketing to engage these enterprises in Miami’s diverse community?

Rich Robert II: “With minority groups, inclusion and appreciation are vital. Today, tech founders and C-suite leaders are incredibly diverse. So, we adopt an inclusive mindset in our Marketing Strategies. Miami’s diversity reflects this, and the world grows more interconnected daily.

Entrepreneurs come in many forms, with varied interests. Thus, for Justworks—especially in our growth phase—it’s crucial to engage these communities. For me, supporting minority subgroups as they pursue their dreams is always a positive move.”