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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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Q&AWhat do VCs do when one of their portfolio companies go IPO?
Generally, they distribute the shares out to their own investors over a period of time (often 8 quarters, as a base case) after an IPO. They often try to sell…
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Q&AIs it a good idea for a person over 75 to start a new business?
I loved this session below with Eric Yuan about starting Zoom at 41. 41 doesn’t seem that old to me (and isn’t 75 for sure), but his real point was…
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Q&AHow much equity is fair for my co-founder that is leaving after 2 years and $50,000 invested in the company? The company is about to launch.
Stock contracts aside, the best you can do is what is fair. Here’s how I might think about it: $50,000 invested at say $1m valuation = 5% 10 year commitment…
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Q&AWhat are some ways to structure an enterprise SaaS deal when the customer is asking for exclusivity against their competitors?
Besides saying No, it’s worth considering a “Free Ice In Winter” approach. By that I mean, a short window of exclusivity for a top customer or partner is often OK…
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Should more companies going public follow Zoom’s example, doing it on expectations for GROWTH instead of for profitability?
Well, Zoom did both. It is both one of the fastest growing SaaS companies of all time AND one of the most capital efficient relative to its peer group. What’s…
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Q&AWhy do big companies buy small companies instead of competing?
Time, and sometimes, talent. Yes, any top-tier Big Tech Company can clearly compete with any start-up. Be under no illusions that they can’t. They can grab 5–25 extra engineers (unlike…
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Q&AHow do enterprises decide which software vendor to sign a deal with?
75%-90% of the time, enterprises have already made a tentative decision which vendor to choose before they pick up the phone or hit the Contact Me button: In an established…
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Q&AWhat are rules your company has out into place to make meetings more effective?
A few things that do help IMHE: A written agenda required for all meetings. No meetings without one. A Principally Responsible Individual for all decisions and actions. For every item…
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When is SalesForce going to buy Oracle?
I think it is unlikely. Salesforce had several discussions over the years re: selling itself to Oracle — when Salesforce was much smaller. But times have changed, the Cloud has…
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Q&ACan you elaborate on the year 2, 3, N referral partner commission for enterprise B2B SaaS?
The biggest difference is the goals. If a partner program’s goal is to align 2 sales teams, then commissions really should only be paid on Year 1 deals closed together….
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We are a SaaS company. A larger partner of ours who sells a complimentary product wants to have their sales reps sell our product alongside theirs. They want 25-50% of the first year’s revenue. Should we do it?
Yes, probably. The simplest way to think of payments to partners is as a marketing cost. The reality is, it’s tough to acquire a good customer for < 20%-25% of…
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Q&AWhat should the dynamic between co-founders be like?
I think there’s one sign you can see in healthy co-founders: if they want to catch up every day. Being a founder and a leader is … isolating. There’s often…
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Q&AHow do I motivate a sales team working commission only?
It is really, really tough. While I am sure there are examples of “1099 reps” that have done extremely well, I haven’t seen it work in SaaS. Pay the reps…
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Q&AIn sales, is it most important to know exactly what a client wants?
Yes, but realistically, the bigger the check size, the bigger the deal, the more important it is. Ideally, very small deals are close to 1–2 call closes. A handful of…
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Q&AWhen Is It “Too Early” To Hire Your First Marketer?
In a perfect world, you’d learn something about marketing first before you hire someone to take it over. I.e., you’d experiment and at least make some progress in: Content Marketing….
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How does Zoom have better streaming quality than its competitors?
I think the meta-answer is that the best of the WebEx team rebuilt WebEx with all their 100s of top people-years of learnings from scratch. As Zoom. CEO Eric Yuan…
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Blog Posts, Q&A, Sales7 Things The Best Sales Reps Get Right
The best sales reps solve my problems: They listen to my actual problems and show me the best solution using their product — and other products. They learn my business…
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Q&AWhat is the best way to protect your IP when showcasing a product to a potential competitor?
There are without question certain cases where your IP is so confidential it simply can’t be shared. In my first start-up, we were acquired by our arch competitor, and we…
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What are simple hacks that salespeople use to confuse customers?
Well I’m not sure confusing customers so that they buy works, but the one tactic that does is FUD. Fear, Uncertainty and Doubt It’s the process of finding weakness in…
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Q&AWhat should an entrepreneur look out for when negotiating a term sheet with a VC?
One simple thing: complexity. 99% of terms and term sheet should be simple and straightforward: price the amount invested (and % ownership for investors / cap table) pool for stock…
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9 Thoughts on What Makes For a Good Pricing Page
What makes for a good pricing page? A few thoughts at least — mainly about what to copy from the big leaders, and what to maybe not copy from them:…
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Q&AWhat are some techniques SaaS companies use to combat trial abuse?
Let it go. A lot of things will drive you a bit nuts when you are small: Folks that do repeat free trials. Folks that share accounts. Early customers that…
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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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