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SaaStr Q&A
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Q&AWhat do founders need to know to successfully navigate a merger/acquisition?
My #1 tip: Get Zen. Once you sell it, it is not yours anymore. And both your upside and your downside are now capped. You can no longer fail or…
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Q&ADo CEOs have personal assistants?
I think a CEO, or at least the founders, should have leverage as soon they can afford it. In both my start-ups, an “assistant” (office+paperwork+EA) was literally the first non-founder+engineering…
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Do all SaaS companies in the USA put late payment fees in their contract?
Many certainly do. Here is the standard clause in Salesforce’s MSA: A late payment fee clause is a good idea, and especially, to place prominently on your invoices. Why? As…
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Q&AWhat have you learned about negotiation and human behaviour as a salesman?
I’m not that great at sales myself (not really), but I am a student of it. A few things I’ve observed about human behavior, negotiation, and good and bad sales…
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What do I do when a solid, late-stage sales opportunity ghosts me?
A few ideas: Invite them to something useful. Invite them to a webinar. To an upcoming event you are doing. To a dinner for top prospects. They might be interested…
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Q&AWill my co-founders buy my shares off me? Our startup has just closed a 15mm Series B round but I want to exit if they will buy me out. The company is burning cash.
If you raised a $15m Series B, these days, it’s quite possible a small amount can be used to buy out your shares. Don’t expect an amazing price, but the…
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What successful startups were launched while the founders worked 9 to 5 jobs on the side?
I’m not aware of any huge successes in SaaS that were active side projects while the founders worked at different companies. But there are a bunch that were side projects…
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If smaller VC funds outperform large VC funds, is Softbank’s Vision Fund destined to fail?
The data in everything in venture is … mixed. Yes, the crazy outperformers in venture are smaller funds, from Lowercase Capital to Benchmark, etc. But the goal overall is to…
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Q&AHas anyone seen termination charges for SaaS services?
Some older companies do this. We were just handed a bill like this for a 20+ year old SaaS product bought out by a PE firm. And really, an “auto-renew…
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Blog Posts, Early, Fundraising, Q&AWhat All First-Time CEOs Should Know About Fundraising
Fundraising … It is sales. It is selling stock. So be very careful with what advice you get. When you have more demand than shares to sell, yes you can…
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Q&AHow long do you have as an SDR/BDR if you aren’t hitting your quota?
I think generally, most sales professionals are given three chances: 3 sales cycles to ramp up for an AE. 3 quarters for field reps (even if they close nothing the…
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Q&AHow much should I charge for a lifetime access to my SaaS that costs $100 per month?
Don’t do it, unless your churn is high or they pay you a ton of cash up front (and $100 a month x any number of months isn’t a ton)….
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Blog Posts, Q&A, Sales5 Ways to Better Motivate Your Salesteam
A few thoughts: First, make sure at least 1 or 2 reps are making a lot of money. This sets an example for everyone. Set up a comp plan so…
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Why do the Slack Founders Stewart Butterfield and Cal Henderson own so (relatively) little of the company’s shares?
Look, a lot of rounds of financing — all the way to a Series H —at almost any valuation do add up to significant dilution: Beyond that, Slack took additional…
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Q&AAs an entrepreneur, what was it like acquiring your first customer?
I had very different experiences. In my first start-up, we were whale hunting — big, large, Fortune 500 customers. So Customer #1 showed us the path to our future. My…
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Q&AWhen does Freemium also work to generate leads for enterprise prospects?
It clearly works sometimes. Two great case studies are Zoom and Slack: In the case of Zoom, 55% of their $100,000+ a year customers start with a free host session….
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Blog Posts, Growth, Leadership, Q&A6 Key Signs a VP Can’t Scale Beyond $5m-$10m ARR
It’s a bit of a bummer than oftentimes, once you finally hire a few great VPs at $1m, $2m, $3m ARR … and they do a great job … that…
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Q&AWhat are the most important metrics for SaaS?
In the early days, there are probably only 5 metrics that really matter: ARR ARR Growth Rate Burn Rate Probably, NPS (more here: I Was Wrong. NPS is A Great…
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Q&ADoes it get progressively easier or harder to scale SaaS as your company grows?
Generally, it gets easier to grow at a “good”/modest rate at you scale, but harder to grow at an outsize rate. Why? Once you cross $5m-$10m in ARR, then usually:…
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Why is Zoom worth more Dropbox?
Both are incredible, iconic companies that dominate a segment of their market. But simply put — Zoom is growing much, much more quickly: Stock prices are (in theory) a function…
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Q&AIs it possible to start a multi billion dollar company in a year?
That’s pretty tough in B2B/SaaS. Brex want from $0 to $1b valuation in 24 months though. That’s pretty extreme. More of the story here; Lessons From a Second-Time Founder: How…
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Are startup CEOs happy?
The best start-up CEOs are: driven unhappy if they are not building truly enjoy doing great things with their team are grateful for those on the journey with them want…
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Career Growth & Advice, Early, Q&A, Sales, ScaleThe Ultimate Guide For Scaling, Sales and Raising Capital in SaaS is Here!
Binge watch 25 of the greatest SaaS CEOs and Founders from companies like Box, Twilio, Zoom and more as they share their inside playbook.
Q&AHow can a SaaS CEO tell which customers are 10+ year customers and which aren’t?
I think it’s fairly easy. Look for: Are they running an entire division or group (or more) on your product? Is the use case mission critical — even if niche?…
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Q&ACan a good salesman sell anything?
Not really in SaaS. At least not well. The classic “Sell Me This Pen” test is still a good one, even in SaaS. There is no perfect answer, but it…
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Popular Q&A
What are some of the biggest mistakes you made with enterprise SaaS sales?
Boy a lot. A list of some of the bigger ones: Not mapping out — and getting to know — all the stakeholders. This is a skill you need to learn quickly in the enterpise. The person that contacts you often is just one of many stakeholders in the purchase. Don’t assume...
How to Price Your Product in the Early Days (Hint: It’s Actually Easy)
Just start with comps. With comparables. Software is very expensive to build, but for the most part, costs almost nothing to ship. It might cost you $0.10 a month in hosting charges per user for an app that isn’t server or storage intensive. So why is one app $5 a...
What is the norm for a “rainy days” bank buffer, considering payroll, rent, and everything in-between?
The best rule I’ve learned in SaaS is the “50% of your ARR on the balance sheet” rule. If you have > 50% of your ARR in cash, in the bank, that’s usually enough to make the key accretive investments you need to make in people, infrastructure and marketing, If you...
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...
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