The ad has been live three weeks. Head of Marketing, Tallinn or remote, competitive package. There are forty applications in the folder and you have read all of them twice.
The problem isn’t volume.
Maybe six are from people actually in Estonia. Of those, two have run marketing at a company selling outside Estonia, and both are employed somewhere you can’t outbid. The rest are capable people who have done domestic marketing for a domestic business, which is a different job from the one you’re advertising.
So here’s the answer, and you won’t like it. Don’t hire a head of marketing. Hire one person to run one channel that is already bringing in customers, rent specialist depth by the hour from wherever it exists, and keep the positioning work yourself for longer than feels comfortable. The head of marketing is your third move, not your first.
The shortage isn’t people, it’s one line on a CV
Estonia’s unemployment rate was 6.6% in the second quarter of 2026, according to Statistics Estonia, having sat above 7% at the start of the year. Nobody is short of applicants.
Now count the pool you actually want. Startup Estonia’s figures put roughly 13,500 people working in the local startup sector, and around 45% of those jobs sit inside the ten biggest employers. Wise, Bolt, Playtech and a few others hold a large share of the bench, and they are good places to work, which is the point. Marketing is a thin slice of any of those headcounts. The slice that has personally taken a product from an Estonian company into Germany, the Nordics or the US is thinner again.
A few hundred people, give or take. Most of them employed and not looking.
That is a supply constraint, not a budget one, and the two behave completely differently. In a market the size of the US you solve a hiring problem by paying more. Here, paying more mostly buys somebody’s attention [and a nice coffee], not their resignation letter.
What the generalist first hire really costs
Do the arithmetic before you commit to it, because Estonian payroll is unusually easy to calculate and founders still skip it.
Social tax is 33% on top of gross, plus 0.8% employer unemployment insurance. So a EUR 2,500 gross salary costs you about EUR 3,345 a month, a little over EUR 40,000 a year. Palgad.ee puts marketing specialist pay in a band from roughly EUR 1,231 to EUR 3,304 gross, and somebody with real export experience sits at the top of that or above it.
Fine. But look at what the money buys in month one.
The first thing a head of marketing does is decide which channels to run. That’s the job. Which means your first EUR 40,000 of marketing payroll is buying a decision rather than any execution, and the person making it is learning your category while they make it.
You can get a better version of that decision out of ten hours with a specialist who already knows the channel, plus your own judgement about your own customers.
In a market with a deep bench, hiring the decision maker first is reasonable, because the person you get has made that call six times already. In Estonia the person who has made it six times is at Pipedrive. Build around that fact instead of arguing with it.
The sequence I would actually use
Four steps, with the signal that each one is due.
Keep the selling yourself. Not the admin, the selling. Founder on the calls, founder writing the follow ups, founder hearing the objection raw. Keep doing it until you can predict the objection before the prospect finishes the sentence, which for most B2B products is somewhere around thirty to forty real conversations. Delegate it before that and you are asking an employee to invent a story you haven’t worked out yet.
Hire one, a channel owner. One person, mid level, on the single channel that produced your last ten customers. Not a generalist. If outbound got you here, hire somebody who does outbound all day. The signal that this hire is due: you have a channel that is working and the founder is the bottleneck on it. Not “we need to do more marketing”. Specifically, a thing that works and nobody to run it.
Hire two, rented depth. The work that needs five years of specialism and ten hours a month is contractor work, and it does not need to be in Estonia. Technical SEO, paid media account structure, lifecycle and email automation, analytics instrumentation. Hire it from Helsinki, Riga, Berlin, Warsaw, wherever the person is. The signal: your one channel works, and the next increment of growth needs depth you cannot train into the person you already have.
Hire three, the person who owns the number. Now a head of marketing makes sense, because the job has become real management rather than invention. The signal: two channels producing, two or three contractors to coordinate, and the founder losing more than a day a week to keeping it all pointing the same direction.
Most Estonian companies I would talk to are somewhere between step one and step two and advertising for step four.
Why renting specialists is easier from here than almost anywhere
This is the genuine advantage and it goes unused.
Cross-border contracting out of an Estonian company is administratively dull. Digital ID and e-signature mean a contract with somebody in Finland is signed the same afternoon. Reverse charge on EU B2B services means the invoice from that contractor is a line in your accounting and nothing more. English is already the working language of most of the sector, so the talent pool is the EU rather than a country of 1.3 million. And the useful time zones, Helsinki to Berlin to Warsaw, are all within two hours of yours.
Compare that with a founder in the US metro trying to contract a specialist in Europe, dealing with a nine hour gap and a different invoicing world.
One thing a contractor cannot do: own your positioning. Who you are for, what you refuse to do, why a Finnish buyer should pick you over the incumbent. That stays with the founder, and it is the same conclusion I reached about selling into Finland and Sweden from Estonia.
The two mistakes that cost the most
The first is hiring an agency before you know which channel works. The agency isn’t the problem, the sequence is. If you don’t know your channel, the first quarter of any retainer becomes discovery, and discovery is paid for out of the budget that was supposed to buy reach. Do the discovery yourself, for free, by looking at where your existing customers came from.
The second is hiring somebody junior and then expecting strategy from them. A smart twenty four year old will execute well and will not tell you that the channel is wrong, because they have no basis for that view and they want the job to go well. You get competent activity on a bad plan, which looks like progress for about five months.
What to do this week
Open a document and list your last ten customers. Next to each one, write how they actually found you, not which campaign was running at the time.
If seven of them came through one route, you have a channel and you know what hire one is. If they came through ten different routes, you don’t have a channel yet, and the founder’s job isn’t finished. That’s a more useful hour than reading another forty CVs, and it is the same test I would apply to what a small Estonian company should copy from the unicorns.
If you want to think through where your own company sits in that sequence, get in touch by email, WhatsApp, phone or LinkedIn for a quick chat. My notes on how I work across these problems cover the rest.