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.

Your Small Business Boom with Steve Strauss [Podcast]

Your Small Business Boom with Steve Strauss [Podcast]

In this week’s episode of the PR Talk Podcast, Amy is joined by Steve Strauss as they chat about contents in his new book, “Your Small Business Boom.” Topics discussed include: pivoting your business, positioning yourself as a thought leader, advertising, pitching, and whether you should be on all social media channels.

Steve is a Small Business Columnist for USA Today and the Founder and President of MrAllBiz.com. Steve is a thought leader, global speaker, spokesperson, content creator, and author of 18 books, including the best-selling Small Business Bible.

Crushing It Online

Amy begins the podcast by asking Steve if he could elaborate on the section in his book titled “Crushing It Online.” The events of this past year and a half have caused many small businesses to struggle, but some excelled. How did those small businesses do it?

Steve explains, “They took either their regular online business and created some extra profit centers to supplement what they’ve been doing. Or they took their analog business and turned it into a digital business and figured out how to do it online.” 

Steve then gives insight into an interview with a small business owner who succeeded in pivoting her business. She had eight infrared light spas in New York that she had to close during COVID. After thinking about what she could do, she shifted her attention to a small part of her spa business, selling infrared blankets. She realized that more people wanted to be comforted as they spent more time at home. That anecdote gave him the idea for this section of his book to encourage people to think about what they can do differently for their business.

 

Positioning Yourself As A Thought Leader

Amy asks Steve if he could provide listeners with some tips on positioning themselves as thought leaders. Steve says that there are two ways to do that: organically and paid. Many small businesses take the organic route. That typically means they’re creating the content, posting it all over their media outlets, and then it’s getting ranked on Google “five years later,” as Steve puts it.

Steve himself has gone that route for many years and encourages people to keep doing that, but if they want to take it to the next level, they must try something else. He believes that the next step would be to put some money behind your content and advertise it. Once you have created a great piece of content, you find an outlet like Google or Facebook to advertise it on and micro-target your audience. According to Steve, there is nothing wrong with advertising your content because it works.

 

Don’t Pitch A Press Release

Amy then goes on to ask Steve, “how do we get attention in your inbox?” Being a USA TODAY columnist, Steve says he receives about 30-50 pitches a day. One thing Steve doesn’t want you to do is to send him a five-paragraph press release. He just simply doesn’t have time for that.

“You want a pithy little email with a snappy subject line that captures my attention, that’s something I haven’t seen before. It’s unique, different, special in some way and it is one or two paragraphs: ‘Hey Steve, I read your column about why college kids should not start a business in a dorm room. Well, I’ve got a kid who goes to UCLA, and he’s making a million dollars a year.’ Oh, that’s kind of interesting! They know my stuff, they know what I write about, they know what I’ve written about, and it’s a different take than I had.”

Steve then shares another way to pitch people, which is to go “old school” by sending them something physical**. It can be something as simple as sending a hand-addressed envelope enclosed with your pitch and some swag. If Steve receives a hand-addressed envelope or package, he is more inclined to open it.

**interestingly this is something that radio personalities Mike & Amy mentioned in one of our first  PR Talk episodes**

Amy and Steve discuss much more in this episode, including millionaire solopreneurs, freelance fortunes, the hub and spoke system, and startups. Listen now to get tips from Steve about how to market your small business and more.

Don’t Miss an Episode

You can access more great episodes by subscribing to the PR Talk podcast on iTunes, Stitcher, Google Podcasts, iHeart Radio and Spotify.

About the guest: Steve Strauss

Steve Strauss is often called “the country’s leading small business expert.” A best-selling author and USA TODAY‘s small business columnist. Steve is an experienced pro who has done hundreds of TV and radio interviews, live appearances, many radio media tours, and much more. Whether you need a keynote, breakout, webinar, tweetchat, or spokesperson, Steve is sure to please.

Connect and follow Steve on social media:

Steve Strauss on PR Talk

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.

Steve Strauss, USA Today: Small Business & PR [Podcast]

Steve Strauss, USA Today: Small Business & PR [Podcast]

Are you ready for Small Business Saturday? 

With Small Business Saturday on the horizon, we think it is a perfect time to rerun our interview with small business expert Steve Strauss.

Pardon the poor audio, it was only episode 30 and be sure to stay tuned (which means subscribe) as we are planning to interview Steve again soon (which will sound much better of course). This episode and blog post originally ran on April 19, 2018 and has been republished on November 20, 2019.

Two of My Favorite Things with Steve Strauss, USA TODAY & Inc.

Mr.AllBiz Delves into the Intersection of Small Business and PR

Luckily Steve Strauss had just gotten fired from his cushy job as a lawyer twenty years ago when USA TODAY came calling looking for a small business columnist. Apparently, the budding entrepreneur wasn’t the best employee and lacked writing ability. He’s gone on to write an impressive 17 books, including the best-selling Small Business Bible. But it’s the brand he’s built through penning a weekly small business Ask an Expert column for USA TODAY that he credits for his success.

After getting the corporate boot, Steve started his own law practice, eventually carving out an interesting niche between three disciplines: law, small business and writing. He has since left the law behind to focus on regular columns for USA TODAY, Huff Po. and Inc. — check out this recent piece for Inc.: “Why Most PR Pitches Stand Out (and How to Make Yours Stand Out).”

You’re wrong if you think Steve couldn’t get any busier. More can be found about how he serves as the small business spokesperson for companies like Bank of America and Verizon on Mr.AllBiz. His team creates written and visual content focusing on the small business community underneath The Strauss Group. And to top it off, Steve’s Web portal, The SelfEmployed, pays special attention not just to entrepreneurs seeking world domination, but also to freelancers and the gig economy, aka the “side hustle.”

Steve’s work could serve as a resource for employed marketers looking to dip their toes into the small business pool through freelancing or side hustling. Most interestingly, we both shared personal stories of how we journeyed into the abyss of the self-employed. Steve’s firing could have been viewed as a failure but instead it led to a much broader, but different, type of success than he ever expected. And although I didn’t know it at the time, saying yes to volunteer work was the beginning of Veracity.

 

This episode of PR Talk covers:

  • How to get in Steve’s USA TODAY column, or the other three notable columns he writes on a monthly basis, and other general PR tips and pet peeves.
  • How and why small businesses should embrace PR.
  • How marketers can start their own companies through freelancing and picking up “side hustles” first.
  • The differences between small marketing shops and large firms.

About the guest: Steve Strauss

Steve Strauss is often called “the country’s leading small business expert.” A best-selling author, and USA TODAY small business columnist, Steve is a global speaker, corporate spokesperson, entrepreneur, and author of 17 books including the best-selling Small Business Bible.

Connect and follow Steve on social media:

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.

PR Talk is sponsored by monday

In such a fast-paced, multi-faceted work environment, it can be tough to stay on top of everything. monday is the collaboration tool trusted by businesses of all kinds to help cut down the clutter and streamline productivity. Learn more at monday.com and signup for a free trial. You’ll see in no time why so many teams around the world are choosing monday for their project management needs.

PR Talk listeners can use the coupon code BetterExecute for a 15% discount.

How to Choose the Right Communication Channels for Your Communications Campaign

How to Choose the Right Communication Channels for Your Communications Campaign

With so many communications channels to choose from, it’s easy to see how some businesses might get overwhelmed.

According to a recent survey by The Manifest, 64% of small businesses use two or more channels when relaying messages to consumers.

By choosing a combination of channels, businesses can ensure their messages are being received by the widest possible audience.

Although it might be tempting to use as many communications channels as are available, businesses would benefit from a more deliberate and mindful approach.

 

Know Your Audience

One of the first steps of planning a successful communications campaign is knowing exactly who the campaign is for.

Ask yourself:

  • How old is the target audience?
  • What are their communication habits?
  • What types of messages do they respond best to?

For example, if your target audience is younger, social media might be the best way to reach them.

Businesses should also consider whether the target audience is current customers or people they’re trying to convert into customers.

“Current customers are going to listen to that message quite differently than folks who don’t know who you are or haven’t had any sort of relationship with you,” said Mike Rosenberg, CEO of Veracity, one of the top PR agencies in Portland, Ore.

 

Consider Your Message

 The next step to planning an effective communications campaign is to consider the message you want to share.

Ask yourself:

  • Are you sharing information about a new product or service?
  • Do you want to share company news?
  • Is the purpose of your message to inform or incite a specific action?

Businesses should always consider the nature of their message before determining which communication channel would be the best fit.

 

Think About What Kind of Return You Want to Gain

After you’ve considered your audience and the type of message you’ll be sharing, you also need to consider the type of return you want to gain from your communication efforts.

Ask yourself:

  • What is the goal with communication to customers?
  • What action do we want them to take?
  • Do we want them to buy something?
  • Do we want them to start a conversation around our brand?
  • Is this more a matter of customer service?
  • How will we track our returns?

For example, if you want to jumpstart buzz around your brand or a new product, social media might be the best channel. If you want to offer customers exclusive news or discounts, email or direct mail might be best.

Whatever your intended return is, make sure it is trackable so that you can measure the success of your campaign to prepare for future campaigns.

 

Business-Consumer Communications Requires a Well-Thought Out Plan

While businesses should use multiple platforms to emphasize their messages, they should do so in a deliberate way. By considering their audience, message, and the return they want to gain, businesses can create a communications campaign that strengthens their public relations, marketing, and reputation management strategies.

Featured image from Ethan Hoover