Imagine this for a moment. You hire on with an enterprise, or perhaps you’re acquired into one, and you want to work with a favorite freelancer that you’ve worked with in the past. Maybe that freelancer writes blog posts or does some impeccable graphic design.
What’s your next move, or even your next thought?
I’m genuinely curious and genuinely asking, because this post is both a framing for market research and the expansion of an offering. I’m trying to confirm a hypothesis here.
My hypothesis is that you think to yourself, “yeah, right, they’d never survive our procurement process” and then you pick reluctantly through an approved vendor list. My hypothesis is that as your business grows, your ability to work with your favorite freelancers shrinks. And I think content folks uniquely value working with favorite freelancers.
How We Got Here: HS as a Content Vendor of Record
Before I meandered my way into owning a marketing business, I used to work as an indie management consultant, often in the enterprise. Often I’d come in as a subcontractor through an approved vendor of record, though occasionally I’d run the gauntlet of enterprise (or once a university’s) procurement process myself. That built me some muscle memory of having the right insurances and negotiating contracts and such.
With Hit Subscribe now eight years old and having moved substantially upmarket, I’ve also now steered us through the same thing, but in the digital marketing and content world. We’ve worked with plenty of large and public companies and are actually undefeated in the vendor onboarding process, from a legal and compliance standpoint. It’s sometimes taken as long as three months, but we have always managed to onboard to become an approved vendor of record when someone wants to work with us.
In one such case, a client contact told us that she really appreciated working with us because we were easygoing and flexible. She liked our large side-hustling contractor bench model. And she also liked the fact that we’d somehow made it through a standard 1099 agreement with that model intact.
She then openly wondered to us whether we could onboard some of her favorite freelancers to that same model, with us basically acting as a brokerage.
Instead of our standard setup of scoping, staffing, and selling content, she would handle most of that herself. Her favorite contractors, her editorial, her project management — her show. Hit Subscribe would onboard her contractors through our normal intake process, handle 1099s and legal agreements, and take care of payroll and back-office concerns, just as we would with our own bench.
Suddenly, we were a content vendor of record.
What This Means for an Enterprise Client Contact in Marketing
This all started two or three years ago. We’ve been refining the operation, doing more and more work, and bringing more contractors into the fold with this. And we’ve expanded to additional client contacts within this organization as well.
What started informally has evolved to be something that I imagine would be pretty attractive to marketers in the enterprise.
Hit Subscribe can onboard as a vendor, and you can direct us to hire your favorite freelancers to our bench. So your favorite freelancers don’t need to go through your procurement process, carry your requisite insurance, sign your standard vendor agreements, agree to your NET-120 payment terms, or anything else like that. We do all of that for them and for you.
You can then bring in your favorite freelancers to work with, give them assignments, set their pay rate, and approve their work. All of this burns down against your budget with us, an approved vendor of record. And this brokerage style work we simply do for a transaction percentage.
Why We’re Well Suited for This
We didn’t exactly set out to do this as a line of business, but we were perfectly positioned for it and didn’t mind it. We’ve expanded the arrangement significantly with the original client and done a few more engagements of this nature here and there, as well. And now, I’m interested in scaling it up.
And here are some reasons that I want to scale it up — some reasons I think it’s a strong value proposition and that we’re well positioned to do it.
1. We’re a First-Class Content Vendor
First and foremost, I’d like to point out that this isn’t some kind of end-run around compliance and controls that an enterprise has in place. We’re not a “content vendor” whose only content operations are sitting between freelancers and enterprise. We’ve been selling content and related services for eight years.
So when you onboard us, we sell credits, and you can use credits for either brokerage arrangements or first-class digital marketing services. We have a deep bench, and bringing your folks into roles alongside those we already have is a very natural fit.
2. We Know How to Structure This With Standard Vendor Contracts
If you like the sound of this arrangement, I can already tell you what your biggest vendor contract hurdles will be to clear.
- You’ll have a contract provision requiring written permission for a vendor to work with subcontractors.
- You’ll probably have payment terms contractors won’t find palatable.
- And finally, you’ll probably have stringent, but not bulletproof, IP clauses around work for hire.
I’ve lost track of how many times I’ve negotiated around this, almost always without even involving legal from Hit Subscribe’s end. Your vendor contract will likely work fine, but we’ll mark it up in a way that allows this arrangement to work:
- Strike the clause around subs or else establish a periodically amended roster for your bench.
- Absorb your payment terms (we pay out NET-15 in practice to your bench, however you pay us).
- Agree to your IP terms and bolster your work for hire claim with an author contract.
What all of this means for you is that we have extensive experience working with enterprise legal and procurement to structure this bench management in a perfectly compliant way.
3. We Carry the Right Insurance and Compliance Footprint
I don’t want to belabor this point, but it is quite likely that an enterprise will require general liability insurance for vendors, among others. We carry the insurances that you need a vendor to carry in order to make this arrangement work. And generally speaking, we have extensive experience with maintaining compliance across the board in a way that satisfies enterprises.
4. We Pay Contractors Quickly and Predictably
We’ve been maintaining a large bench for many years, which builds up a degree of sophistication around accounts payable. We collect invoices throughout the month, run them through work confirmation and (when applicable) client sign-off on the 2nd, schedule them for payment, and dispatch AP on the 15th of each month.
For your contractors, this means:
- Keep track of work completed throughout the month.
- Invoice by the 1st.
- Receive payment (out to them on the 15th).
- Have transparency into invoice status at all times.
This is more reminiscent of a monthly payroll than it is of how you pay your vendors. And best of all, you’re never playing messenger between contractors wanting to know about payment and your accounts payable group.
5. We Have the Broader Operational Infrastructure
We have a buttoned-up intake process for contracts already, whether they’re yours or part of the Hit Subscribe community and bench. And we also have pre-canned Airtable bases for you to manage your budget, bench pay rate, and sign-off on work ready for invoice payment.
We’ve built this muscle over the years and scaled gradually. So adding your contractors to the mix is barely a blip in the scheme of things. We’re already running this system month in and month out.
6. We’ve Proven It Works at Scale
This isn’t a theory. It’s been narrow and somewhat opportunistic up to this point, but we’ve handled in excess of a million client dollars in the brokerage models alone, keeping everything organized, getting everyone paid on time, and generally making all participants happy.
7. We Might Already Be on Your Approved Vendor List
Obviously this isn’t a given, but there’s a chance your company has already worked with us in some capacity. We’ve been around a long time– and we’ve been dealing with large organizations for a long time. But we’ve also worked with a lot of startups that have been acquired into larger organizations. In one case, we have even made it through recursive acquisitions, working with an enterprise who had acquired a company that had acquired another company we started working with in 2017.
So you never know. You might be able to engage us without any lead time at all.
Why We Want to Expand This
I like to think of Hit Subscribe less as a content seller and more as a strategic partner that solves business problems — business problems that happen to revolve around content. And I perceive this as a potentially major pain point for enterprises in need of some relief.
Compared to other disciplines, marketers — especially those trading in content — seem disproportionately likely to build up a rolodex of favorite contacts and freelancers. And content creation is true gig economy stuff.
This makes it far harder for enterprises to generate content than it is for smaller, more nimble organizations. And it’s not like enterprise marketing FTEs are any less busy or any more likely than marketers at their smaller counterparts to have time to sit around banging out blog posts without distraction.
I think we can engineer a pretty nice partnership concept here. You know who you want to work with, what story you want to tell, and how you want them to tell it.
We want to let you handle all of that stuff — the stuff that makes you a good marketer. Let us handle the boring stuff for you.
What I’d Like To See Next: The CTA, As It Were
First of all, if this seems interesting to you, let’s talk. You can book a discovery call with me if you’d like.
Usually, when I’m in market research mode, I inoculate against worries of a surprise pitch by saying, “I’m just asking some questions; I don’t have anything I could sell you even if you wanted to buy.” But this isn’t one of those times — if it would help you, I can sell you this.
But zooming out a little, what I’m really looking for is confirmation (or refutation) of my hypothesis. My hypothesis is that a lot of people in the enterprise would love to work with freelancers around content, but that the realities of existing in the enterprise make this either an onerous chore to arrange or simply an impossibility. My secondary hypothesis is that if we could make it possible and not a chore, people would take us up on that.
So even if you don’t want to book a call or have any kind of serious conversation, I’d just love to know about the experience of trying to hire or work with freelancers in the enterprise. What’s hard? What’s not hard? Have some enterprises solved this problem? Are there vendors of record already well established and doing what I’m suggesting?
All of your thoughts, questions, insights, and feedback are welcome.








