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SaaStr Q&A
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Q&AAs the CEO of a startup, what should I tell my employees who keep asking for raises after they realized we just raised a new round of funding?
Two meta-thoughts: First, you have to decide if you are going to “hold the line on burn” after a fundraising. If you plan to — tell everyone. They will get…
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Q&AWhat are some of the best founder exits from a start-up?
Probably deals where the founders made > $1b each. The data here isn’t my strength, but let’s make a partial list for U.S. start-ups pre-IPO: WhatsApp Founders, $5.5b (+-) each…
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Q&AShould all CEOs be required to have annual leadership training?
Required is a strong word … but the answer is Yes. Everyone can benefit from leadership training. Especially, the folks so senior that traditional training doesn’t cover them. Who trains…
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Q&AWill individual employees ever be able to sign up for SaaStr Pro for personal Learning & Development? Has there been any sort of traction for this idea? (i.e. Treehouse)
Probably not for a little while. We tried this in the beginning, but there just was too much “sales” friction for an individual vs. a team. We want to get…
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Why did Slack file for a direct listing rather than an IPO?
Because you save a lot. You save a lot on dilution, and a bit (but not THAT much) on fees. When you IPO, you generally sell 15%-20%+ of the company,…
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Q&AWhat #1 factor can sales teams implement to improve overall sales performance?
Training. Training the single most important factor you can do to increase sales team performance: Onboarding properly. Initial co-calling and co-selling. Building collateral the team can use. Creating scripts for…
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Q&AAt what stage should a startup hire a CMO?
Roughly, when Demand Gen is no longer the core function of marketing. This also often is the time when you are ready to expand beyond a core small, effective, efficient…
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Q&AHow do corporate venture capital firms different from conventional venture capital firms?
They aren’t as dependable. This doesn’t mean they are “worse”. It does mean be careful how you use them. This is issue #1. A few like Salesforce Ventures and GV…
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Blog Posts, Exit Strategy, Q&AWhy Founders Leave After Acquisitions
Why do founders leave after their companies are acquired? There are many nuanced answers, but in the short and medium term, it’s incentives. Acquirers use 3 incentives to get founders…
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Blog Posts, Customer Success, Early, Q&A, Sales Strategy5 Tips To Minimize “Churn and Burn” Behavior in Your Sales Team
As you scale your salesteam, unless you are very careful whom you hire and how you train them, incentives being what they are in variable compensation, some negative behavior will…
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Q&AWhat does a CEO do to deserve such an exorbitant salary?
I struggled with this myself a bit in the early days. In the end, there is a simple answer: the CEO is the one responsible for the entire plan. Everything….
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How are seed investors in a SAFE protected from a venture capital recap?
SAFEs are actually surprisingly investor-friendly in several ways. They are very founder-friendly in that they transfer no ownership, votes, or other “say” in the business initially. Investors have almost no…
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Should Elon Musk pay his employees enough for them to be able to purchase Tesla’s vehicles just like Henry Ford did?
The math likely doesn’t pencil out — way, way too many cars to sell. But he did sort of do this with their first car — the Tesla Roadster. Tesla…
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Blog Posts, Career Growth & Advice, Early, Q&AThe Best Advice I Ever Got From an Investor
The best advice I ever got from one of my angel investors: Stop feeling sorry for yourself. I went to meet with one of my angels and mentors when things…
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Q&AIs it possible to guide against salespeople taking the B2B sales relationships with them when they move to a competitor vendor?
Well, sort of. Certainly, this is one benefit you get from using Salesforce or Pipedrive — data doesn’t walk out on their laptop as much as the old days. A…
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Q&AHow long should I give commission on recurring subscriptions to my salespeople for?
I think most folks (including Twilio, etc) have realized you pretty much have to pay salespeople the way they are used to be being paid: on the annualized value of…
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What prompted you to sell your startup?
I’ve been through it 3 times. Once as a start-up exec, and twice as founder. The first time, the answer was price. In my first start-up job, we were acquired…
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Q&AShould co-founders issue themselves 100% of the issued shares at founding, or vest over 4 years?
There are fewer bigger mistakes you can make as a founder than not having 4+ vesting. Ideally, a decade. Why? Because vesting protects the most committed founders from the least…
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What are the economics of angel investing?
There is a lot on the topic, but I thought it might be fun to look at how my first 9 angel investments have done. We can learn a lot….
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Should I cap the commission of my salespeople so they don’t unfairly earn more than my other workers?
Not until the company is very big. It’s often the case that top sales reps close 2x to as much as 5x as much as an average rep. With the…
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Q&AWhat 3 mistakes did you make in your SaaS that you wish you could go back in time and fix, to accelerate growth?
Every year I think about it, the top 3 sort of change. But my Top 3 mistakes I made as a SaaS CEO: Not constantly hiring, especially for VPs. You…
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What will cause venture capitalists to try to force founders out of their companies?
A lot has changed in the past decade. Today, the vast majority of traditional South Park / Sand Hill type VCs want the founder-CEO to go the distance, if at…
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Featured Q&A, Q&AIf we have two overlapping products is it better to have one sales team or two teams?
It’s almost always better to have different sales teams handling different products Why? If for no other reason — Incentive Alignment. Sales reps work on commission, and they are driven…
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Want to Get Ahead in Sales? Make Sure You Pick the Right Track
It is important to decide which of 3 life tracks you want to be on: Super-successful sales rep / individual contributor. I.e., make $200k or even $500k+ someday, just closing…
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Q&AWhen did you know you wanted to be a CEO and not just a founder?
It wasn’t always clear to me. In my first start-up, I was the one that put it together, and was the “business/sales guy”, and was the one that raised the…
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Popular Q&A
If we have two overlapping products is it better to have one sales team or two teams?
It’s almost always better to have different sales teams handling different products Why? If for no other reason — Incentive Alignment. Sales reps work on commission, and they are driven almost entirely by what they get the most commission for. When they sell 2...
Want to Get Ahead in Sales? Make Sure You Pick the Right Track
It is important to decide which of 3 life tracks you want to be on: Super-successful sales rep / individual contributor. I.e., make $200k or even $500k+ someday, just closing deals yourself. Crush your number, live the life, take nice vacations, wear expensive suits,...
How difficult is to become a venture capitalist after 45?
It can be harder than you might think. The further you are along in your career, the easier it is to have the time, networks and personal capital to be an investor. No question. And it can take a decade or more to make any real money from investing. It’s hard to have...
How would Slack fare against Slack alternatives in the next 4 – 5 years?
Slack has become a platform. Every developer, and every company that wants to integrate with in-stream communications, integrates and builds on Slack. All of them. Chat is nothing new and the core “chat” part of Slack has been and will continue to be cloned and even...
Have you invested in a company before companies pre-IPO? How much ROI did you get?
So far, my ‘13–’15 investments are at about 10x. My ‘16-’18 investments are much earlier, and are sitting just under 2x. A few lessons for me: “Power laws” is an annoying phrase, but they do matter. Your top investments will likely return the bulk of your returns. A...
What successes have you had promoting your business on Twitter?
Social overall is a surprisingly small percentage of traffic to SaaStr.com: But of the Social segment, Twitter is the #1 performer this year to SaaStr out of all Social channels: Having said that, given how much work Social is, it’s not clear it’s worth it for us for...
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