Episode 051 — The Digital Broker Podcast

Outsourcing Done Right: The Insurance Agent’s Guide To Upwork


In this episode of The Digital Broker, Steve and Ryan discuss the benefits of outsourcing via freelancing platforms like Upwork. By listening to this episode, you will learn:

  • Why freelancing platforms are the way to go for any agency looking to outpace the competition by achieving more goals
  • The basics of putting together a job listing, posting it on Upwork, filtering applicants, and selecting who to work with
  • Which issues come up most often—transparency, accountability, and payments—and how to deal with them

There are times inside an agency when it feels like everything is happening at once. Various to-do items trickle down and overwhelm the people at their desks. Sometimes, there simply isn’t enough time or personnel to do everything. Other times, some items will require technical skills nobody possesses. Either way, you’re stuck with two options.

Eliminate some items.

Or outsource them—but how, and to whom?

There used to be no easy way to deal with that, but today there is. Thanks to web-based freelancing platforms like Upwork, agencies have immediate access to millions of specialists and contractors who can deliver work competently, affordably, and on time.

Upwork is perhaps the best known of these platforms, and the one we will use as our default. On Upwork, you post a listing detailing what you want, what your budget is, and which criteria you’d like to filter applicants by—for example, you might be looking for specialists exclusively in the northeastern United States. Once you’ve posted the listing, contractors bid for the opportunity to take on your project, sometimes by volunteering to do it for less than your stated price.

Suppose your agency’s goal is to grow revenue by 10%, and part of that is to be driven by digital marketing. First, you should have a good talk with your team about what exactly you will need some help with: probably not the whole project, but some component that is outside of your available time or skillset. (7:16) For example, you determine that your website needs some better landing pages, but you don’t know the first thing about them. Right away, you can get a digital marketing consultant on Upwork to advise you; some will get on the phone with you for as little as $50 an hour.

Now that you know a little more about landing pages and what yours ought to look like, you discover that nobody in your agency knows how to put one together, so you decide to outsource that on Upwork as well. You do this by writing a description of the kind of landing page you’re looking for and how much you’re willing to pay; the more specific you can be, the better. (10:48) If you’re too vague about your expectations, you’ll end up wading through submissions that don’t come close to what you have in mind. At the same time, be open to options. Your best bet is to let the contractors know what your fundamental requirements are—that your niche is this, that your colors are these, that the message has to be so-and-so—and then give them space to wow you with their ideas.

Once you post the listing, you’ll be surprised at the speed and number of bids you’ll receive, especially if it really does have to do with website design. (Upwork is teeming with developers.) It is not uncommon to post a website-related listing and have around 20 to 30 bids on it an hour and a half later. (16:04) The diversity of the applicants can be staggering; same with the price range at your disposal. Some applicants will charge as little as $5 an hour, while others are considerably more. Your standards and your budget will help you narrow down the field. So will the platform, which is rich with filtering criteria.

That’s the process in a nutshell, and landing pages are just one example. You can use Upwork to get help on just about anything. Have your producers been clamoring for a more digitally dynamic proposal, but nobody at the agency can design one? Upwork. Are your PowerPoints putting people to sleep, but everybody at the agency is too busy right now to go spruce them up? Upwork. Do you have some killer ideas for illustrations to enhance your marketing material, but your team can barely operate Microsoft Paint? Upwork. If you can break a job down into manageable, block-sized pieces, you can get somebody to do it for you on Upwork.

Agencies that leverage platforms like Upwork will get a lot more done and thus outpace agencies that aren’t anywhere near the platform. Still, we keep hearing the same objections to outsourcing work over the web like this, so we’ll address them here.

First, people can be stingy. When you see what someone is charging to do something you know you could do yourself, the impulse to economize kicks in. “$200 for that? I could do it myself for free!” Yes, you could—but should you? Is it worth your time? How long will it take you, seriously? Wouldn’t you be better off working on something else?

There is also some concern about who you’re handing off the work to. Is it safe to let total strangers into your agency’s operations? (19:01) We don’t recommend a carefree attitude here. Don’t invite unknown individuals into private spaces like personal servers and data stores. But when it comes to cooperating on more public-facing deliverables, like apps, illustrations, webpages, etc. we think you can let your guard down a little. Remember that Upwork tries to make it easy for you to screen applicants according to your standards and other criteria. Ratings, reviews, and information about the contractor’s history on the platform are all good indicators of reliability and trustworthiness. You could also take your chances on a less experienced contractor and expect to pay a little less since new arrivals typically undercharge in order to compete with the veterans.

Finally, there is the question of accountability. How do you know that the contractor is actually doing the work you’re being charged for? (24:22) First of all, rest assured that every project gets funded in escrow. If you choose to pay by the hour, you can use software that screen grabs your contractor’s screen every five seconds. You can also cap the number of hours you’re willing to pay for so that the contractor doesn’t take you for a ride. If you’re paying per project, you can do so in installments, releasing parts of the escrowed funds only when the contractor reaches milestones that you define. Suppose you have commissioned a suite of 12 blog posts. You could set a milestone at every 3 articles; when the contractor turns those in, you review them, and if you’re satisfied, you pay and move on to the next milestone. If you judge the work to be unsatisfactory, you can interrupt the engagement before it goes any further, or even file a dispute. Just make sure that you communicate well and behave reasonably because contractors are going to be rating you on those things as well.

If you’re still squeamish about outsourcing work over the web, you can come to tell us your concerns at the Digital Broker LinkedIn group. Maybe you’re onto something that we missed on this episode and can address on a future one. Or maybe some of us have been in your situation before and can guide you to some solutions. We won’t know until you speak up, so start posting here.

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