The Resilient Entrepreneur, Edition #101
Hi there
I hope you had a great week!
Here are the topics in today's edition:
- 250 Touchpoints Later: Data-Driven Lessons From Enterprise Sales
- The Startup‑Politics Mismatch: Four Checks Every Country Needs
Please reach out with comments, questions, or suggestions for articles!
Talk soon,
Tom
TACTICS FOR RESILIENT ENTREPRENEURS
250 Touchpoints Later: Data-Driven Lessons From Enterprise Sales
Enterprise sales are different from B2C sales: Sales cycles are longer, you have to talk to many different people, and it’s not done once the sale is complete.
At the end of each year, I review my files, notes, and contacts to keep things organized and clean up digital clutter.
The end of 2025 was no different. This year, I focused on organizing my personal notes, which I keep in Obsidian. I like Obsidian because it visualizes connections between different notes and topics.
My cleanup session revealed how many meetings and calls it takes to close and maintain an enterprise deal. Yes, that’s counterintuitive to all the hypergrowth talk that shaped the fat years that lie behind us.
Let’s look into some details of a few enterprise deals I worked on at Yonder, the B2B SaaS company I co-founded.
1. Sales cycles take longer than you think
No investor likes to hear that sales cycles can take longer than one year. But it’s a fact in many B2B markets. At Yonder, we are active in the aviation and critical infrastructure verticals, with sales cycles taking 1–3 years. That’s because customers usually make decisions only after an RFP process, and because winning an RFP means shaping it long before it is published.
Do you think I’m exaggerating? Do you think I’m trying to find excuses why hypergrowth doesn’t work in B2B? Let’s look at some real-life examples pulled from my personal notes in Obsidian:
Enterprise customer #1:
- Number of meetings and calls: 65
- 1st meeting: April 24, 2019
- Contract signature: August 19, 2020
Enterprise customer #2:
- Number of meetings and calls: 253
- 1st meeting: August 13, 2019
- Contract signature: May 21, 2021
Enterprise customer #3:
- Number of meetings and calls: 384
- 1st meeting: January 23, 2018
- Contract signature: March 31, 2023
To make sure the data is comparable, I have only included data from deals that I led from start to finish, from initial sales talks to RFPs and customer success.
2. Involve multiple people to get a deal done
Let’s dig a little deeper into why sales cycles are so long in the B2B and enterprise markets. Again, my notes database in Obsidian proves useful: I didn’t just link the company name to each meeting but also the names of the people attending each meeting. From this, I can see that many people were involved in the sales discussions.
In contrast to B2C, where each potential user is also a potential buyer, you have to speak to many different people when selling in the B2B domain. Sponsors, main users, procurement, legal, everybody wants a say in the discussion. That’s one of the core reasons why sales cycles are so long, and why you will need to schedule so many meetings and calls before closing an enterprise deal.
To make things worse, large organizations often do internal reorganizations, which means you will get new points of contact, and you will have to start all over again with your sales pitch.
3. After closing the deal, stay in touch regularly
Closing the deal is one thing, but it’s not the whole truth. Once you’re in business with a B2B or enterprise client, you will have to nurture the client constantly. If you don’t do this, you risk losing the client. Here are some reasons why you will have to do this:
- As many people were involved in the sales decisions, you want to make sure your key users like and understand your product.
- Onboarding sounds simple, but it isn’t. You want to keep an eye on the speedy rollout of your product for your customer to get the maximum value out of it.
- Yes, even after contract signature, enterprise customers undergo internal reorganizations. Whenever the point of contact changes at an enterprise customer, you will have to spend extra time to fully onboard the new person to your product. From my personal experience, taking key person changes too lightly is a main driver of customer churn — especially when they happen before onboarding is completed.
Last but not least, even when after landing an enterprise deal, you want to materialize an upsell, don’t you? I’m afraid you won’t be able to do this if you don’t talk to all sorts of people at your customer’s organization.
STRATEGIES FOR RESILIENT ENTREPRENEURS
The Startup‑Politics Mismatch: Four Checks Every Country Needs
Startups and politics are misaligned in many countries. Here are four checks every country needs, using Switzerland as an example.
Founding and growing a company is hard. Finding investment for your startup is even harder. But once you’re there, another administrative challenge awaits: You will need to get the funding registered and your company incorporated.
Sounds easy? At least in Switzerland, my home country, this is not the case. It is a costly, time-consuming, and paper-based process. I know this from my own experience as the Founder & CEO of Yonder, a B2B SaaS company.
And yet, politicians from left to right aren’t shy to tell the world what a wonderful startup ecosystem we have in our country.
Let’s run an entrepreneurship/politics reality check that can be applied to any country.
Check #1: The Political Lobby
If you don’t have a lobby in your national parliament, it will be difficult to achieve your goals. Ask the farmers or the lawyers, they know. Both professions have a mighty lobby, because many parliamentarians are either farmers or lawyers.
What about entrepreneurs? In the 200-seat lower house of Switzerland, only a handful are founders or entrepreneurs, and another handful are CEOs of larger companies. So it’s no wonder that the political framework for startups has lower priority than agricultural policies and legalese.
Check #2: E-government Infrastructure
My special love for lawyers is well-known to those who read my articles regularly. It’s this profession that created all the legalese that makes founding and capitalizing a company cumbersome, paper-based, and expensive.
I can buy a car, pay by credit card, and walk up to my new car that already sports the new license plates. The purchase is a fully digital process, including proof of insurance and proof of identity. Why can I not incorporate a company digitally?
I can buy a second home halfway across the country without seeing a notary. Sending an apostille, the mortgage confirmation from my bank, and wiring the money is enough. The next step is to get the key from the real estate agent. Why can I not perform a capital increase fully digitally?
In Switzerland, we tend to explain to the world why our processes make sense and why they should remain unchanged. Hey, we’re a successful country, so why change?
That’s dangerous. Other countries move much faster with process digitization. Think of Estonia, the digital frontrunner among European countries.
Check #3: Culture of Failure
It would be too easy to rant about politicians and lawyers making my entrepreneurial life oh-so-miserable. Besides the political lobby and the e-government infrastructure, entrepreneurs need a society with a healthy culture of failure.
In this respect, Switzerland can learn from the United States. Failure is common among entrepreneurs, as creating something out of nothing is risky and doesn’t always end well. The Americans know, and society accepts and even honors entrepreneurs who tried and failed.
What about the Swiss? Failed entrepreneurs are stigmatized, their careers often curbed. As a consequence, entrepreneurs often take lower risks, which leads to smaller, less successful companies in the long run.
Check #4: Venture Capital Market
In most cases, building a company is expensive and requires upfront investment. That’s why entrepreneurs need access to a vibrant venture capital market that shares their appetite for risk-taking and growth.
Switzerland is a small country, which means it has a small home market. In contrast, the United States is the largest single market in the world.
When you start a company, getting started in the largest market in the world has obvious benefits, especially when your product is designed for global markets such as aviation.
That’s why the United States has a much larger and more vibrant venture capital market than Switzerland. Nevertheless, there is no obvious reason why a rich country like Switzerland cannot create VC funds deep enough to fund the next Google or OpenAI. The money is available, but Switzerland lacks the political will and the risk appetite.
Conclusion
In any society, entrepreneurs fuel innovation. They invest their blood, sweat, and tears to create innovation, progress, and value. The least politics can do is to set the general conditions for entrepreneurs to thrive. In contrast, many political systems overload entrepreneurs with unnecessary admin work and fees.
And, my dear politicians, even if this worked in the past, don’t rest on your laurels: The world is changing fast, and many other countries crave to become the next economic superpower.
Your entrepreneurs are your secret weapon. So the least you can do is to create favorable conditions for them to succeed.
About Me
Growing a company in uncertain times is like running a marathon — it demands grit, strategy, and resilience.
As a tech entrepreneur, active reserve officer, and father of three, I share practical insights and write about entrepreneurship, leadership, and crisis management — no AI bullshit, no promos, just my thoughts in plain text.
When I’m not solving problems, I recharge and find inspiration in the breathtaking mountains around Zermatt.
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