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Enterprise Prospecting Mastery

by Doctolib, Sales in DACH
Aug 19, 2026

"I get so many calls and emails a day. In the end, every vendor does basically the same thing. So honestly, I don't care who does what anymore."

- a Cold Call Response from a Prospect

That's the market we're prospecting into. And that's why today we show how Jannis Ruß maps prospecting across 4 evolutionary stages:

  1. feature-based selling ↓

  2. solution-selling ↓

  3. value-selling ↓

  4. trigger-selling.

Classic feature-based selling is dying. Buyers decide emotionally and justify rationally. And in enterprise, where dozens of stakeholders are involved, solving your champion's problem isn't enough.

You have to show value to every person in the room, including the influencers who feel no acute pain and the ones who simply don't want anything to change.


 

3 Best Practices Jannis swears by

1. Persistence + multichannel

Some of his biggest accounts took many months of consistent effort before Jannis even landed a demo (not a deal, a demo!). His takeaway for every enterprise SDR and leader: don't lose your nerve when it takes a long time. That's just the nature of the segment.

Our favourite Jannis Sales Secret is a handwritten Christmas card 🎄 😍

After months of trying to reach one decision-maker, he sent a personal, handwritten card. Her reply: "Whoever puts in that much effort, I can't keep ignoring."

Try it for Q4 and tell us how you go!

2. Prioritise ruthlessly and cluster by industry to become the expert

When Jannis rebuilt his enterprise motion, they listed every prospect and sorted them by hard parameters:

  • open roles

  • ICP fit

  • potential ARR

  • ...

The result was a clear ranking: the top handful of accounts were worth six-to-seven figures each, while an account near the bottom of the list might return a fraction of that after a full year.

That ranking is key! Top accounts got escalated to C-level to activate networks and referrals. And crucially, it gave him more meaning in the work. He knew one account could be worth more than ten others combined.

Clustering by industry is the multiplier here: go deep in one vertical and you start sounding like an insider, not a vendor!

3. Do the Deep Research

This is the heart of the enterprise craft. A good outreach, Jannis says, needs two things:

  1. Relevance (a real reason you're reaching out)

  2. Individualisation (something specific to that person).

His research ritual before any call, mail, or DM:

  • Company news: Google the account, hit the News tab, scan for fresh triggers

  • The annual report: Not all 250 pages, but Ctrl+F the outlook, the management foreword, the highlights, the opportunities-and-risks section for keywords and numbers you can hook into

  • The person: Their LinkedIn, what they're actively posting about, interviews, podcasts

Living in the time of AI this has become much easier too, IF you have the right set up! Connect all 3 data sources, link it to your Slack channel and stay updated! If you need help with that, reach out to us and we'll connect you to the Expert you need!


 

The Enterprise Blueprint

Here's how Jannis strings it together on a real account:

  1. Build the prio list: Rank your target accounts by revenue, headcount, potential ARR

  2. Map the stakeholders: Enterprise means many contacts per department. Filter LinkedIn down from hundreds of possible contacts to the specific decision-making unit and sketch the reporting lines between them

  3. Run the outreach sequence: Connect on LinkedIn (his tip: NO message first!), then a targeted email, then a LinkedIn video once they accept, then (most important of all) call them. In parallel, work the influencers and engineer warm intros through your own C-level


 

🎯 You want more than this?

Then join us on the 3rd!

 

On September 3rd, we're interviewing Camille von Arnim, Sr. Director Sales at Doctolib, and former Head of Growth Sales at Amazon and ask what navigating both Enterprise and Scale Up companies really look like!

  • What's genuinely different day-to-day?

  • How does the money and the growth really look like?

  • How does Family Life look in both set ups?

  • What type of Sales Rep are you?

Camille has built and led sales teams on both sides and is the perfect person to discuss what best path fits you!

👉 Save your spot and register now


Still struggling with your Performance?

Let's talk! We'll find the problem and solve it together!

Your Sales in DACH Team ✨

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