As you scale, you need to expand your team and start delegating tasks. That can be as daunting as it is exciting, especially as you start to hire new employees and get them trained up to work alongside you.
And eventually, you’ll scale to the point where you may need to outsource work even beyond your existing team, relying on agencies, consultants, or freelancers to help with everything from accounts payable to content and social media marketing.
Many businesses struggle to know when it’s time to outsource, and to determine which elements of their business would best be handled by an external team member instead of an internal one.
Good news: This is a challenge many business owners and department leaders have faced before.
We talked to three business owners with extensive experience in the topic about their opinions on outsourcing, including when to get started and what to hand off, and today we’re going to share what they had to say.
Knowing when it’s time to find a third-party to come in and help with a select task is crucial. How do you know when your team needs the extra help when there are so many factors (including training, budget, and time) to consider?
Massimo Chieruzzi, who runs DivByZero, was a Co-Founder of AdEspresso, and is the Co-Founder and CPO at Breadcrumbs, said it’s all about opportunity cost.
"In early stage businesses, you have a limited amount of time, resources and skills and you should focus them on what really adds competitive value and build your unique value proposition,” he explained. “Everything else is just a distraction.
As an example, for my personal blog, DivByZero… I know how to build a website in Wordpress very well. Yet what's gonna make a difference for the success of the blog is the content and I decided from the get go to focus my limited amount of time on writing great content, delegating the website management to an agency.”
Dave Shanley is the CEO of Content Camel and works as a growth advisor for businesses like Kosli after extensive entrepreneurial experience. He said that there are two areas of consideration when outsourcing tasks like marketing: getting more done, or specializing in skills that your internal team might not have.
“For moving faster, sometimes that’s as simple as kicking off a campaign where the internal team is already fully committed,” he said. “When seeking outside experts in specific areas – like SEO – the internal team has probably covered that up until now, but you’re looking to increase the effectiveness of the time spent there.”
Gaetano Nino diNardi, a growth advisor for brands like Wagepoint, Cognism, and Splash, strongly recommended that at least for marketing, businesses should be focused on the “moving faster” aspect that Dave commented on.
“It’s much better to outsource in order to run faster, save time, or non-critical functions that don’t require a full-time headcount,” he explained, sharing that he thinks most structural elements like website design should be done in-house.
When we asked our experts about the biggest advantages of working with third-party vendors, they all talked about that “moving faster” aspect discussed above. There’s no denying that outsourcing means you can pick up steam quickly.
So time aside: What are the advantages to working with freelancers and agencies for outsourced work?
“The biggest advantage of working with outside resources is that you get to quickly test new areas, validate them, and expand or pull back efforts,” said Dave. “It’s all about experimentation and figuring out what works the best in the lowest friction way possible.”
Gaetano also stressed the financial benefits, noting that outsourcing to third-parties allowed for flexibility and scalability simultaneously, allowing you to keep full-time headcount low. And, as a plus, “businesses can write off fees from agencies and service providers.”
Knowing what to outsource, obviously, is a massive part of the process. And our experts each had outstanding advice to share.
“If there's a limited budget, you need to make fewer bets with greater confidence, rather than several bets with lower confidence. ICE prioritization method might be worthwhile in this scenario,” Gaetano said. “Outsource based on expected business impact vs. timeline to results.
“For example, if the SEO opportunity in a given industry is massive, and there’s zero SEO investment, it might be worthwhile to consider SEO — however the downside is that it will take 6-12 months before you start seeing returns.
“On the other hand, if there is an opportunity to test the waters with affiliate marketing, perhaps this should be prioritized since time to results is much shorter.”
Massimo, on the other hand, noted that he’d prioritize any tasks that required specialized knowledge to make a difference for the business.
“I would prioritize activities that require high skills and experiences to have a meaningful impact,” he said. “As an example, using a good template, you can build a decent looking website internally. On the other side activities like advertising or conversion copywriting requires a lot of experience to deliver results. Either you have someone in the team already highly skilled, or it's better to outsource then to waste months building the internal skill set with mediocre results.”
And Dave noted that “right now” priorities should always be given consideration when choosing outsourcing options.
“Like anything else, make sure you understand fully – and communicate to the team – what the objectives are,” said Dave. “If you focus on the outcomes first and work backwards, then you’ll have better results all around. The reality is that you always have limited budgets, so make sure you’re focusing on the high priority outcomes for the business right now – move the needle immediately.”
When it comes to choosing who to outsource to, the most common solution is the easiest one: Referrals.
“Vendors often come by word of mouth,” said Dave. “Other teams in your network have likely solved for some part of what you’re evaluating to outsource and, if it’s working for them, then you can start there to de-risk your decision. Beyond that, who do like-minded operators in the wider community recommend?
“What doesn’t work is blindly searching and choosing a vendor based on simple searches or ads. Dig in and really evaluate if you’re hiring the right group for the areas they excel in.”
Gaetano echoed this sentiment:
“My view is that any referral based methods of hiring contractors is usually the best — this is obvious since their work is verified by a trusted 3rd party whom you already know.
“The next best method would be tracking them down on LinkedIn or X — start with a small test project to see their quality of work in real-world scenarios before committing to a big venture.”
One common question that many businesses have when outsourcing any task is to choose between freelancers or agencies.
“Freelancers and agencies both have their place.” said Dave. “Freelancers are a perfect fit if you need small scale augmentation of the internal team – and you have the internal team time to manage and support the freelancers.”
And his opinion on when to use agencies:
“Agencies are a great fit if you need more complex services, need the management help that can come built-in with agency relationships, or also need help in an area that the internal team simply doesn’t have depth of expertise with.”
Gaetano noted the value of freelancers, stating “Freelancers are a great bet for many situations — especially highly specialized marketing roles such as link building, conversion rate optimization, or freelance SEO copywriting.”
Okay, you’ve settled on the type of work you want to outsource, and you know you either want to work with an agency or a freelancer.
Now it’s time to actually select that third-party to outsource to… and it’s important to be able to watch for red flags in the process.
And one red flag is one you might not expect: Someone who claims to do too many things in supposedly-specialty services.
“You generally want to avoid service providers who offer ‘too many things.’ The jack of all trades, master of none is usually the biggest red flag to watch for,” Gaetano shared, especially regarding high-skilled services like copywriting. “Other obvious ones are no verifiable published works or no verifiable references.”
And sometimes, even a highly skilled agency or freelancer just isn’t the right fit. A lot of it comes down to the style of work.
“When outsourcing work,” said Dave, “pay close attention to communication (is your inside team good at communicating, how about the vendor?) and level of organization (can your team handle managing the vendor, and is the vendor organized?). A breakdown in either of these areas is going to mean a major headache.”
Outsourcing isn’t as simple as delegating a task to someone on your internal team, who is already hired, trained up, and ready to go (even if they’re busy).
The best service providers may have a waiting period, and it takes time no matter what to find the right vendor, go through negotiations and onboarding, and actually get started.
So when should a business get started?
“Everything takes longer than you think it will – so plan accordingly,” said Dave. “Outsourcing is really about augmenting the internal team, so it’s going to take some internal time to execute regardless of how much is being done outside the walls of your organization – don’t forget to include that in your estimates.”
Gaetano recommends always trying to have at least a one-month cushion when outsourcing any projects.
“There are always inevitable roadblocks that pop up,” he explained. “However, one of the biggest benefits of outsourcing is that you can often get deliverables completed in two weeks, given the agile nature of working with contractors.”
Outsourcing may take a little trial and error. You may even go through a vendor or two while finding the right one— sometimes it just isn’t a fit, or you realize that you have other priorities elsewhere. That’s okay.
No matter what, remember that when it comes to outsourcing, always be crystal clear in your communication.
As Dave says:
“Successful projects are built on clear communication, so write everything down that you expect from the relationship and work. Be explicit at every opportunity. Be open minded about achieving the objectives, because great ideas can come from outside the internal team as well.”
So start with transparency and clear instructions regarding your goals, your expectations, and any vision you have. A great vendor will be able to build off that and get you the results you want.
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