Hiring An Ad Sales Team

It’s official, our sponsorships closing service is live! WOOOO!

It’s imaginatively called Deals as a Service, launched with Jack Pilcher, a fellow British-ad-sales beast. He’s helped Chartr get acquired by Robinhood as the 1-man sales team.

Early results for a few lucky clients are super promising. We’ve been busy hiring a team of elite media salespeople.

Hence, this issue of Revenews is all about hiring an ad sales team.

Emotional rollercoasters aside, let’s dive in! 🚀

📰 Newsletter News

🤝 A Media Operator acquired Toolkits, here’s why

📈 B2B ad sales in 2025 (great insights in here!)

😷 Advertisers have accepted that brand safety is a myth

📊 How this journalist doubled her paid Newsletter subs

👏 Kit continues to capture to celebrity newsletter market with Tom Brady

⚖️ The for and against for spending $8m on a Super Bowl ad

⬆️ How this chap gained 16k followers almost overnight

Hiring An Ad Sales Team

🥅 Job Postings

A few people have asked, how do you find good people? Nothing sums up my thoughts better than this meme.

Yes, referrals, can be great too, but still not a guarantee that you’re locking in a superstar.

Bonus 

The best hire is someone you’ve already worked with closely, so start there. Build a list of people you’d love to hire one day.

🧲 Attraction The right Person

What Type of person do you want?

After re-hashing the same job post 7 times, when I lead with the character of the person we’d love to hire, I found two absolute gems of individuals.

Requirements and responsibilities are great, but describe the person and your vision for working together. Your ideal person will then read that and think, ‘fuck yeah’.

If you don’t know the type of person you want, write it out.

🎮 Using LinkedIn’s Job Posting Feature

For how big of a platform LinkedIn is, I am constantly baffled at how poor their job posting experience can be (and ads for that matter). So this is how to best navigate the actual posting with/without spend.

You can post a small number of job posts a month for free, and they tend to cap you at around 70 applicants, after that they make you put spend behind the posting. Fair enough.

My first time around, I put in £54 of spend, instructed over 2 weeks. That spend was eaten up in 2 hours, with only 5 additional applicants. Customer Success were extremely unhelpful but did eventually begrudgingly refund. I’ve found the best way to approach it is:

  • Use the free postings first, putting spend behind it doesn’t actually increase the number of applicants.

  • Once you get capped, put the minimum daily spend possible (for UK that’s £6).

That approach for me gets the most amount of qualified applicants without throwing money down the drain.

Make sure you also use the qualifying questions when setting up the post.

🎯 Interview Process

✅ Key Qualities to Look For

Some of these are subjective preferences, but generally, this is my view of the key qualities of a great salesperson.

  • Personable/likeable

  • Have that ‘self-starter’ attitude, intuition, drive

  • Fantastic verbal communication

  • Ruthlessly organised

  • Good at thinking on their feet and solving problems

  • Good listeners

  • Tech-savvy

⛔️ Two common (incorrect) myths:

  • Hiring extroverts - being an extrovert does not translate into sales success, statistically the best salespeople are ‘ambiverts’, i.e. a little bit of both

  • Hiring experience - I’m not saying never hire someone with 5+ years experience, but across multiple companies, I’ve seen that people hired for their experience work out a LOT less than people hired for their character.

🕵🏻‍♂️ How to Get to Honesty

Interviewing is a funny old thing. If you ask ‘What do you value?’, the prospect will answer with something they think you want to hear. So instead of asking these types of questions directly, spin it around and focus on asking them what they’d like in a workplace.

Our most impactful interview question has been:

“What do you look for in a workplace? A team Dynamic? A culture?”

This is great because you’re genuinely asking about what they’d want, but you’re also indirectly asking, what are YOU like? If they value a hard-working quick-moving culture with open communication, they’re probably honest and hard-working. Tick!

📊 Organisation

Seems obvious, but when interviewing, make a spreadsheet, and create categories on which you rate people. Leave room for subjective ‘vibey’ stuff, but keeping organised and quantifying hiring will help you make much higher quality decisions, and give you more confidence in that person.

🤓 Onboarding

The first onboarding will never be slick and smooth. Accept that, and try to prepare as much as possible to cover all the bases.

The onboarding topics that seem to be universal for me:

  • Systems/accounts set up

  • Specific role details

  • Wider company education

  • Client/account education

  • Timeline synch

  • Meet the others

  • Sales fundamentals

  • Initial sales homework

  • Values/expectations setting

🎥 Record Everything

It’s so easy in 2025, so make use of one of the 7,245 AI recording tools. In my opinion, Fathom is the best, you can get a free month here. Apollo’s free version is also decent, great considering it’s free.

Record (and properly document) everything is useful for a few reasons:

  • Recorded training sessions can be re-used for future new starters.

  • If you have significant disagreements with that employee, you have the real conversations recorded to reference.

  • You can watch back and improve on your own communication. This has helped me become a LOT more concise. Trim the waffle.

🎭 Personalised Schedule

Set a schedule for each newcomer, this includes a timeline of progression, learning, topics and so on. Just make sure you leave flexibility within the to meet people where they are in terms of skills, tech savviness and personal commitments.

Structured but accomodating.

That’s all folks. I was thinking about doing a section here on training, but I think that’s a whole other beast, so I’ll do a dedicated one on that…

Does all this sound like a lot of hassle? Just let Ad Sales as a Service do it all for you...