6 More Things You’ll Look Back On in SaaS … And Regret

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What’s my list of SaaS regrets? 

Well, I dug into a few of them last Friday, but let me dig into a few more of them here, so that maybe by challenging you a bit, you do just one more thing in SaaS you could have done, you know you should have done … that pays off 1-5 years down the road. Maybe pays off big.

#1. Not Having Had More Folks in Customer Success. 

You’ll likely look back and realize you put too many folks into sales roles versus customer success. You’ll see this helped you maybe make the quarter, but maybe, also miss the big picture. For any SaaS vendor with net negative churn, the sale is just the start of a decade-long journey. You’ll never look back and regret not having more CS coverage. You’ll never look back and regret segmenting your CS team too early. Or adding an EMEA CS team too early. Etc. etc. Try to get 1 CS pro per $500k in ARR. Maybe even more, if you have a few nickels. If they are good, you’ll never regret it.

#2. Losing a Few Top Logo Accounts You Could Have Kept If You’d Gone There, or More Often, or Been More Involved With. 

Very related to the prior point, but worth digging in on Logos in particular. You will regret any top logo you lose that you could have saved. If Google or Salesforce or Shopify leaves you to go to a competitor, that’s a triple blow. You lose the revenue. You lose the logo. AND you lose all the referrals for the next decade that would have come from that logo.  You just can’t lose the key logos. They are just too hard to win, too value, too accretive to your brand.  So first, overstaff them. If need be, assign a Total Potential Value to them if the deals start small, and staff them per TPV, not current ACV. Second, consider a VIP CS rep just assigned to logos, especially smaller ones that still have high value. And finally, you have to go there. Yes, you the CEO. If you go, ideally at least twice a year, they will likely stay.

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#3. Not Leaning In On Biz Dev, Partners & Ecosystems — Hard. 

Partner marketing and partners-as-a-channel can seem super frustrating at first. You spend months building an Appexchange integration, or Slack integration, or Shopify integration, and then … nothing. No leads at all! Or maybe just a couple. And it seems like so much work, for so little gain.  But the winners go long here. They know that ultimately, there are just a few winners and tons of non-winners on and in every platform.  The #1 key is getting help once you have even a hint of success on a platform. Hire a head of business development early. As soon as you have any traction with a key partner or on a platform. Your competition will. You need to box the competition out, and box your wins in, in any ecosystem you can. It may take 2 years for it to feel worth it. But ultimately, winners align with winners. You want that to be you.  Lean in with biz dev and partner marketing dedicated hires as soon as you have any traction in an ecosystem or a platform. Even if it doesn’t really seem profitable yet. If you don’t, you’ll look back in a few years and see this as a huge missed opportunity. When the other guy pulled ahead there, somehow.

#4. Founder Conflict. 

Founder conflict is common, and a little of it may even be good. But later, you’ll look back and see that keeping a toxic founder around even a month longer than necessary inflicts substantial damage. Toxic employees are bad enough. Toxic founders threaten your entire mission, and everyone’s confidence. The simple fact is, many times, not all the founders are equally committed. It is what it is. But solve founder conflict, or at least, resolve it. Now. Stamp it out early by talking and meeting more. Get a 3d party to help you work through it. And if it crosses the line to un-fixable, then it’s time. Time for one of you to move on. The missed opportunities to scale, build, compete and ship are just too large in SaaS. You’ll look back on founder conflict as just a lost era, a whole phase when you couldn’t move the ball forward. And when the competition did.

#5. Raising Money From Any Investors That Didn’t Help.

 This is a subtle one, but one you will regret later. The cap table unfortunately only adds up to 100%. 🙂 That means that any investor that doesn’t truly add value is … a waste. A waste of a slot on your cap table. No matter how cool their offices, great their brand, or clever their tweets. Each % on the cap table has to add value, or it’s simply wasted space. So if you do have options when you raise money, really ask how they can help. It doesn’t have to be epic. But most investors don’t really help. Not really. And you’ll look back, and wish for that % on the cap table, you’d gotten some help.

#12. Excessive Fear About Competition and Big Cos Crushing You. 

Worrying about the competition is healthy. But what I find is that most founders read too many tweets and press releases from the competition, and don’t focus enough on what really matters. What does?  Agility.  If there are multiple competitors in a space, each past Initial Traction, the most agile one often wins these days. Brand is #1 in winning a market, no doubt. Most later adopters just want to pick the default choice. But Agility is probably #2. If you can push out 100 features a year, and they can only push out 20, and you focus, focus, focus … you can pull ahead. Maybe not in a week. But definitely over time. And at least, you can stay even. So if you are worried about the competition, figure out how to get more agile. How to push out more story points, more integrations, more key features for your top customers and prospects. And figure out in which segments of the customer base agility lets you win. If they can’t do the same, that’s a strategic weapon.

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