To close out SaaStr Europa 2024, Jason Lemkin, SaaStr CEO and Founder took the stage to answer the audience’s most burning questions. AMA’s with Jason are wildly popular for his expertise and no-holds-barred delivery. Let’s find out what people are asking in H2 2024.

How Do You Sift Out the Bitter and Broken Individuals When Hiring?

As a startup, most people who come to an interview appear happy. How do you spot the ones who are burnt out?

  1. You interview 30 people.
  2. If it’s a role you’ve never hired, find someone great at it and have them do your final interview.

To determine if someone is bitter and broken, you have to ask a lot of open-ended questions. For sales, product, or customer success, the best question you could ask is, “What would you do your first couple of weeks?”

Don’t ask about the first 30 or 60 days because they’ll think about their plan. What do the best Heads of Product and VPs of Sales say? They’re going to meet customers for the first two weeks. They’ll talk to 20 people to figure out what’s working and what’s not.

Not everyone loves meeting customers. Don’t hire those people to lead.

Can Early-Stage Startups Run PLG and Enterprise GTM Motions at the Same Time?

“PLG is just freemium with analytics,” Jason says. You can measure it, and we’ve been doing it since 1996 with the first web apps. Almost everyone who starts as self-serve or PLG adds more sales over time. Canva and Asana began as self-serve, and Canva just held an Enterprise event. Asana has flipped to having more sales-led motions than self-serve.

For the most part, we all end up with this model. When do you know the right time to do both? If you don’t already do self-onboarding and procuring, it’s wildly difficult to add later.

What Jason does is have folks create a pie chart. How many of your customers are small, medium, and large? You decide how to define that. If it’s 40% small, 40% medium, and 20% large, you can project out what that might look like at $10M or $100M unless the market or you change it.

If you have no medium or large customers, you’d probably do better to stay at the bottom of the market for now. Shopify stayed at the bottom of the market well past IPO.

If the pie chart is heavily Enterprise, but your VCs are telling you to go down market for faster deals, should you? Not if you have no customers there. As a founder, you have to decide what your organic customer base is telling you.

Don’t listen to your VCs. They aren’t building your products or listening to your customers. If you’re thinking about adding on PLG or a sales motion because it’ll be easier, don’t. Nothing is easier. Do them because that’s what your customer base is telling you.

How Do You Categorize Revenue for VCs?

Say you’re a company growing 100% with decent margins around 80%. But, you have situations where you aren’t classifying revenue as revenue and could pull in an extra million ARR while dragging down gross margins. What should you do, and how do VCs look at this?

In the old days, we were super gross margin sensitive. When Twilio started to scale, people said it was the Stripe of communication, but VCs were wary because it had 40-50% margins. Both were right.

Twilio is an iconic generational company trading at a pretty weak multiple because of margins. In 2021, no one really cared or looked at gross margins and mostly wanted top-line growth. Public markets didn’t care either (a slight exaggeration).

Today, public markets care to an extent. A software company needs to be north of 70% margins. But to be tactical, many VCs still care about top-line growth.

If you have communications, software, and another source of revenue, be honest and do three colors on your revenue stack. Shopify,, and Toast all do it. Let VCs come to their own conclusions.

Are Marketing Agencies Worth Investing In?

“Hiring a marketing agency is the fastest way to flush your money down the toilet,” Jason shares. A great founder was a couple of months in, and things weren’t working, so he decided to hire the best marketing agency in Southern California. It’s only $100,000, and he’d do a big launch around it.

Three months later, he got some nice collateral and a good 2×2 on the industry but no leads. Of course, there are gems within marketing agencies and professional services, but, for the most part, that’s in a person, not an agency.

Your best bet is to hire someone who knows how to do it for real rather than someone using templated emails with 20 clients they know little about.

As a VC, Should You Ignore Founder Logos?

VCs looking for founders to invest in is a little different from founders hiring executives and VPs. When hiring leaders within your company, you should cover up a person’s work history logos on LinkedIn and determine if you’d still hire them. For a VC, you don’t want to be blinded by logos, but scaleups do breed entrepreneurialism.

To find the best startups, you have to find the people other people don’t find, or you have to win. To win, you have to be in all the deals and beat the other people. Later-stage venture is more about winning, and early-stage venture is about finding hidden gems.

Venture is a sale and hustle business. You have to build a network of feeders, and build relationships with people who are one stage earlier.

What Should Happen After You Close a Deal?

Customers churn if implementation isn’t good. What are the best practices for what should happen after you close the deal? There are many best practices, and it can be hard if you have too many customers. But one of the best things you can do is set up three calls with new customers at 15 days, 45 days, and 90 days, or whatever variation makes sense for your company.

Do those calls yourself and with your team. The three calls are a great framework, and then you back into what the KPIs are under it. Force it to be documented with senior leadership so you can surface issues and measure them.

What percent are onboarded in the fastest time possible? Make that a core KPI to drive it up. Almost all founders find that fewer customers are onboarded as quickly as they think. Ideally, 90% of your customers are onboarded in the shortest period. Measure it constantly and use that to spot issues.

Advice For Companies Looking To Raise During A Downturn

How should you approach it if you’re doing well in today’s world and looking to raise? First off, congrats! Second, assume you have to talk to more VCs than you’re used to.

Don’t play any games or artificially constrain the process. Be a little more chill and talk to twice as many as planned. There are so many variables to raising money.

  • Not everyone is in market.
  • You may not be the type of AI someone is looking for.
  • You may be asking for too much.

When you reach out to investors, make an effort.

  1. Ensure your deck is updated whenever you send it out to someone new.
  2. Make that person feel like they’re one of your top choices.
  3. Pay attention to what each investor is looking for.
  4. Be a little conservative in your asks.
  5. Be more chill and more respectful.

You can always raise more than you ask for; being conservative might increase the odds of being funded during stressful times.

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