If you haven’t read it yet, head on over to Part 1 of Ask Me Anything with SaaStr founder and CEO Jason Lemkin to learn about sales in SaaS, how to create great SDRs and AEs, developing an impactful content strategy, and potential SaaS trends for the next 12-18 months. 

In Part 2 of Ask Me Anything, Lemkin will answer these questions:

  1. How do you balance being authentic as a new startup and getting customers to buy into your vision vs. appearing well put together with everything going on?
  2. How do you fix GTM?
  3. Will there be any new categories in the next 5-10 years? 

Question #1: Do You Show Up As A New Startup To Get People To Buy Into Your Vision Or Present Yourself As An Established Startup With Everything Going On? 

Some sales folks might disagree, but Lemkin believes startups should be about 85-90% transparent. 

If you’re a new startup, maybe you have your first couple of AEs, or you’re figuring out product market fit, or you just don’t have a big enough brand or cash in the bank to sell to big companies, you need to strike a balance. 

If you exaggerate too much, you’ll get caught. 

Big Enterprises are taking a risk on you. 

They’ll ask for financials and a balance sheet, and if you lie and say you have $50M in the bank yet only have $60, you’ll lose the deal. 

If you say you’ve done the SOC 2 and you haven’t (which you should), they’ll trust you in the beginning until you get caught. 

The reality is…

In Enterprise, they formally or informally have a second set of criteria for emerging vendors. 

They understand the need to bring in a handful of emerging vendors each year that solve holes. 

How can you stand out as an emerging vendor in SaaS? 

If you solve a very specific need that no one else does, and if you have a champion who vouches for you, the standards are lower. 

Everyone has a lower but genuine bar for emerging vendors because you can’t have it all when you’re not public. 

The interesting thing is…

A lot of the best built-out programs for emerging vendors are in security. 


Because you can never solve every security hole in Enterprise, it’s an amazing space because it’s never solvable. 

You have to try new vendors because the attacks are new every year. 

The best advice for emerging vendors trying to get into Enterprise is…

Let them guide you through the process. They’ll know the risks they’re taking. 

Question #2: How Do You Fix GTM

The high-level advice for founders trying to approach Go To Market differently is…

Don’t worry too much about innovation in sales and marketing. 

Don’t look for magic bullets that aren’t there. 

The entire time Lemkin has been in SaaS, many things have gotten better. 

Once upon a time, we didn’t have Gainsight, or Gong, or Zoom. 

If you step back, the basic motions haven’t changed.

Doing outbound well, customer success, account management, and marketing tools are radically different, but the idea of communicating on multiple levels of drip marketing, personalized content, events, webinars, etc.

None of that is new. It’s just getting better. 

Everyone talks about PLG, but old-timers agree that when people say PLG, it’s just instrumented premium. 

So many get into trouble on burn rate and try to go PLG to fix it. But it doesn’t fix it. Re-inventing the wheel doesn’t fix anything because the basic motions still exist. 

Just because you put up a new self-service function that you’ve never had and probably doesn’t work because you didn’t architect your product for it, you won’t magically change the trajectory of your company. 

Pick Something You Know And Do Your Best At It

When you have no help or executives, pick something you know and do your best at it. 

Email still works. 

The world’s best email to a prospect who needs your product always works. 

If you’re great at marketing, go do marketing. 

But at the end of the day, you’re still doing the same stuff of the past two decades, just with faster and better tools.

There’s no silver bullet or magical tweet storm or agency to do short-form videos that will change the face of your company. 

There are no shortcuts. 

You have to put in the hours on things that work. Figure out what you’re good at, and don’t lower the bar. 

Hire great people, and they’ll run with it. 

Read this: If You Don’t Think You Need A VP of Whatever, You Haven’t Worked With A Great One

On the GTM side, when you’ve met a truly great VP of Marketing or Sales or Customer Success, you’ll change your mind. 

You need a VP of everything, and if you think you don’t, go meet a great one. 

Question #3: Will There Be Any New Categories In The Next 5-10 Years? 

Are there any areas of Enterprise transformation that are still untouched? 

Founders of 8-9 years ago were asking the same question…

Are all of the categories taken? 

Now, we’ve got AI, and people question whether all traditional categories are done. 

Lemkin has learned that every five years or so, or 5-7 years in Enterprise, categories get reinvented. 

There’s usually a reason for it. It could be AI. It was mobile 6-7 years ago. 

We don’t know where today’s tech and platforms will take us tomorrow. 

People asked if we needed another email marketing platform, and now we’re looking at the first SaaS IPO to file in two years at $650M ARR. It’s profitable and growing by almost 60% — Klaviyo. 

We didn’t need another marketing solution, but they specialized in eCommerce and Shopify, and that level of deep integration with Shopify data remade a category. 

What will explode? 

Lemkin’s not sure, but he knows these categories remake themselves every 5-7 years. 

Find The Area Being Disrupted Or Where It’s Too Small For Big Companies To Pay Attention

If it feels like you can’t break out in a category, find the area being disrupted. Or, once something gets big, find a niche too small for them to pay attention to. 

Klaviyo targeted eCommerce. 

Zendesk is pretty good, but the eCommerce segment wasn’t worth their time. To grow 20%, they needed to add $300M a year. So they didn’t have time for the tiny corners and niches. 

Fast forward, and Gorgias targeted that “little” segment and has more revenue than that entire niche did 6-7 years ago. 

Niches that grow will constantly disrupt categories in the way leaders see but can’t care about. 


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