Working with Marketing Contractors: How to Find the Right Fit, Build Trust, and Keep Work Flowing

Working with Marketing Contractors: How to Find the Right Fit, Build Trust, and Keep Work Flowing

The workforce has changed, with many marketing professionals preferring flexibility, independence, and remote collaboration. That’s why Veracity has built a blended team of full-time staff and trusted contractors to attract top talent and reflect how people want to work today. Whether you’re leading a nonprofit, business, or in-house marketing department, knowing how to find and manage marketing contractors is an essential skill.

This post continues the two-part series that began with Successful Agency Partnerships: How to Know If You’re Ready, Choose Wisely, and Keep Them Working. While that piece focused on managing agency relationships, this one looks at contractors — the individuals who fill specialized roles, expand your team’s capacity, and bring expertise when and where you need it. Both posts are adapted from my book A Practical Guide to Public Relations for Businesses, Nonprofits and PR Leaders.

Knowing When You Need a Contractor

Contractors can be an efficient, strategic way to fill gaps, test new initiatives, or handle overflow work. They bring experience and flexibility without adding long-term overhead.

You might consider bringing in a contractor when:

  • Your in-house team is stretched thin but you’re not ready for a full-time hire.
  • You need specialized skills (like design, writing, or SEO) for a defined project.
  • You want to pilot new marketing initiatives before committing long term.

Working with contractors allows you to scale up or down as needed — a practical solution in an industry where priorities change quickly. Contractors are also an important part of blended teams, balancing long-term internal knowledge with on-demand expertise.

Finding the Right Fit

The best contractors are professionals who treat their independent work as a business, not a side gig. When evaluating potential partners, look for experience, communication skills, and reliability.

A few key criteria:

  • Professional training and track record. Have they been mentored or worked within an established organization before going solo?
  • Consistency. Contractors who’ve been independent for several years tend to be self-managed and reliable.
  • Tools and resources. Established contractors invest in their own equipment and software.
  • Communication. Pay attention to how they write and respond. Clarity, tone, and timeliness matter as much as their portfolio.
  • References or testimonials. A short list of satisfied clients or published examples of their work speaks volumes.

Referrals are the best place to start — ask trusted peers who they rely on. When that doesn’t surface anyone, use job boards like PRSA or AMA, or vetted platforms such as Upwork. Just make sure to maintain transparency by communicating and paying through the platform if that’s where you connect.

Setting Expectations and Deliverables

The most common reason contractor relationships fail is lack of clarity. Both sides should know exactly what’s being delivered, how often, and to what standard.

This can be as simple as outlining specific monthly deliverables — for instance, the number of content pieces, social posts, or design projects due each month — paired with agreed-upon timelines and revision processes. Defining this from the beginning helps prevent confusion and ensures you’re both measuring success the same way.

When starting out, it’s fine to work hourly while testing the partnership. Just set a maximum number of hours and review early progress to make sure the arrangement is productive. As trust builds, move toward a structure that rewards efficiency and accountability for both sides.

Practicing Delegation and Building Trust

Delegation takes practice — especially for leaders used to doing everything themselves. Early in my career, I over-edited every piece of work my contractors submitted. I thought I was helping; I was really creating delays.

That changed when I worked with a contractor who quickly learned my style and started producing work that exceeded expectations. By gradually handing over more responsibility, I built trust — and gained time to focus on strategy and leadership.

If delegation feels uncomfortable, start small. Assign one clear deliverable, review the results, and expand from there. Over time, you’ll learn how to communicate expectations without hovering.

Managing Long-Term Relationships

Once you’ve found great contractors, keeping them engaged is key. One of the best analogies I’ve heard came from a Fortune 500 marketing leader who described his contractor network as his “bench.” His strategy was simple — keep the bench warm.

He made sure contractors always had small but steady projects so they stayed familiar with his brand, team, and systems. That way, when a major initiative came up or someone left the team, those contractors could step in immediately without a long ramp-up. It’s a smart approach that creates loyalty, continuity, and a reliable safety net — the same kind of stability that makes blended teams so resilient.

Paying and Classifying Contractors

There’s no single right way to pay contractors, but retainers tend to work best for me. They make budgeting easier, provide consistency, and reinforce accountability. When we agree on a set scope each month, both sides know what to expect — the contractor has stable income, and I can forecast expenses without surprises.

At Veracity, this model works across all kinds of contractor roles — writers, designers, digital specialists. Everyone has a clearly defined set of deliverables tied to a retainer, which keeps the focus on outcomes rather than clocking hours. It’s a system that values results over time spent.

Paying hourly can make sense in the beginning, especially when testing a new contractor or defining a role. But it has its drawbacks. Some tasks take minutes, others take hours, and the hourly system can underpay efficiency. A retainer rewards skill, speed, and consistency — things that benefit everyone.

Whatever structure you choose, be clear about expectations and communicate regularly about scope or timing changes.

Proper classification matters, too. Laws like the “ABC Test,” adopted in several states, outline who can legally be considered an independent contractor. In general, they must:

  • Be free from your direct control
  • Operate outside your core business functions
  • Maintain an independent trade or profession

These rules protect both sides. Respecting contractors’ independence while staying compliant isn’t just a legal necessity — it’s good business.

Tracking Performance

Even if you’re not paying hourly, it’s still smart to track time. Tools like Toggl help teams understand where effort is going, whether deliverables align with investment, and if workloads are balanced.

For contractors, time tracking isn’t about micromanagement — it’s about transparency. It helps identify where efficiencies can be improved and ensures both sides feel the workload and value are fair.

Building the Modern Team

Managing contractors effectively is as much about mindset as process. Flexibility isn’t a trend; it’s how the best work gets done today. Contractors bring specialized skills, independence, and fresh perspective — qualities that strengthen teams when managed with trust and structure.

By combining full-time employees with reliable contractors, you create blended teams that are efficient, scalable, and modern. It’s how Veracity works — and how many successful organizations are operating now.

For more detail on managing PR and marketing teams of all types, including additional processes, examples, and checklists, you’ll find expanded guidance in my book A Practical Guide to Public Relations for Businesses, Nonprofits and PR Leaders.

Staying Ahead of the Digital Curve: The Point of PR is Not PR [Podcast]

Staying Ahead of the Digital Curve: The Point of PR is Not PR [Podcast]

A Frustrated CEO Podcast interview with Leb Tannenbaum, Patrick Lyons and Patsy Feeman

Amy had the opportunity to be a guest on The Frustrated CEO Podcast with hosts Leb Tannenbaum, Patrick Lyons and Patsy Feeman. She shared how to leverage current news and employee passions to position a company’s core values and culture, connect with internal and external audiences, elevate visibility, and position industry thought leaders.

After listening to Amy share her advice and tips, The Frustrated CEO gathered actionable steps for staying ahead of the digital curve. See our favorites below:

  • The 4th Quarter is when to create your marketing plan for next year. Like each of the other critical functions in your business, it’s important to plan for how you’ll market and brand your business in the coming year, and the 4th quarter is the time to do it. As Amy Rosenberg said in the episode, don’t overthink or overcomplicate it. Focus on what’s going on for you and your audience, then how and when you want to communicate about those things. If you need help, check out Amy’s blog post here, which gives more context and offers a simple grid to complete. 
  • After you’ve built your marketing plan, schedule a year’s worth of monthly meetings to keep you on track and help you execute it. If you’re not meeting rhythmically – at least once a month – to check in with your team on the marketing plan, your chances of fully executing it greatly diminish. And some would argue if you’re not going to execute the plan, why bother wasting valuable time and money creating it in the first place? If you want to realize any ROI on your marketing plan, you need to come together to review your strategy, adjust it as needed, review drafts of future communications, and identify potential PR emergencies that you should begin to prepare for now.
    • PRO TIP: If your organization doesn’t have its PR or marketing team, you can still accomplish this by engaging others close to you, either inside or outside the business, to help you strategize and create a plan. Look for someone detail-oriented to assist in creating the plan, while someone more creative might be better suited to help shape and craft the messages you publish. 
  • Do this to take your marketing to the next level. Identify the top 3 audiences that align with your top 3 goals, then be specific in your marketing plan about how you’ll communicate with and engage those audiences. You likely already know who those audiences are. Be intentional about who you tailor your messages and content to. Just don’t overthink it. Go with your first instincts.
  • You can attain thought-leadership status. According to Amy, all it takes to become a recognized thought leader in your space is taking everything out of your head and creating content with it. It’s that simple. Start by creating content from what you already know. You don’t have to know the most; just be willing to share what you know. It’s not only good for your company, but in time it will position you as a thought leader in your space, all for just talking about what you know.
  • Let your Core Values guide your marketing and PR. You have core values for a reason, and this is a great opportunity to show everyone they’re not just words on the wall or in the handbook. Let them be the filter through which you create and review your messages, craft your responses, position your brand, and engage with your customers. Be sure to lean on your values when responding to hot-button issues or landmine topics that are difficult. If your core values are considered in all these scenarios, your marketing and PR will be authentic and consistent. 
  • Toot your own horn once in a while. Congratulations! You or your company have won an award or been recognized for something positive and good! Now it’s time to share the good news with the world. Don’t be afraid to share news of the awards you’ve won, testimonials you’ve received, community involvement you’re engaged in, or any other way you give back or have been recognized. You likely don’t realize how often the good things you do go unannounced to your employees, customers, and the community at large, and each of those is a missed opportunity to highlight the good things you do.
  • Your culture and purpose are interesting to the outside world. If you’re looking for more topics to use when creating content, don’t forget to post about your company’s purpose and vision for creating value in your industry, community, and world. Your culture and core values are also great topics that tell the world about you and can serve as your differentiator or competitive advantage when attracting new talent. Consider highlighting your employees who exemplify the culture, core values, and company purpose. Let them tell your story in their own words. These are popular business topics today, so don’t be afraid to create content around them. 
  • Your clients and customers can also make for great content. You’ve got great customers, people and businesses doing cool things. Use your marketing efforts to highlight them and tell their stories. Making others look good always reflects well on you, so include your customers in your marketing plan. 
  • Be strategic and intentional about being in the press. Some have said that any publicity is good publicity, but anyone who has navigated through a crisis knows some publicity can be painful and damaging. Therefore, be thoughtful and planful about when you want to be in the public eye and when you don’t. You don’t need to weigh in on everything or be always visible. Let your Core Values guide your thinking, and know when to say yes and when to say no to being in the press. The more intentional your strategy and aligned your team is around it, the more likely you are to control the messaging out there about you.
    • PRO TIP: Use this same approach when deciding which social media platforms you’ll engage with. You can’t do everything, so be strategic and thoughtful about where your customers are and what you can handle. Rather than do everything with moderate success, know when to say yes and when to say no to certain platforms, and then give it your all to be a strong presence on whichever you’ve chosen. 

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About The Frustrated CEO


The Frustrated CEO guides its listeners through the journey of leading in the most powerful and influential way. With episodes twice a month, the hosts interview CEOs from diverse backgrounds to offer systems for greater influence, action and success while increasing a sense of satisfaction and well-being. Listen to their latest episode here

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This episode of PR Talk is brought to you by PRSA Oregon

Throughout Oregon and Southwest Washington, PRSA provides members with networking, mentorship, skill building and professional development opportunities – whether you are a new professional fresh out of college or a skilled expert with 20 years in the industry. Check out PRSAoregon.org for more information on how membership can help you grow and connect.