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Career Growth & Advice, Growth, Q&A, Sales, Sales StrategyWhat is the biggest challenge salespeople are facing when it comes to closing deals (last stage of the sales funnel)?
Urgency. Urgency does not really exist in 95%+ of deals. There really is no burning need for most customers to buy today, this month, or often even, this quarter. The…
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Growth, Leadership, Other, Q&AIs Quora at risk of another question and answer site emerging? I have been here a few years and Quora seems to have slowly but continuously gotten worse as they attempt to generate more revenue.
I don’t think so. Not until the paradigm changes. Here’s why. Quora has a unique combination of: The largest on-point audience, and By far — by far — the best…
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For how long should a CEO continue being the head of products?
Roughly for me, for as long as it’s about a 10-hour a week job. Or often, maybe only up to $3m-$5m in ARR or so. In SaaS at least, founders…
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Q&AA partner in a top tier VC who funded our competitor is interested to invest on us and even gave us couple of good intro to potential customers. He claims they have separate funds in different locations, so it’s not a conflict. Should I trust him?
Maybe. A few thoughts: First, conflicts are somewhat fluid and even subjective and not AS big of a deal as some make it out to be. I know this is…
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Career Growth & Advice, Exit, Exit Strategy, Leadership, Q&AWhat did it feel like to exit on your first business?
Much better the first time than the second. The first time we sold, I had far exceeded any expectations I had as a founder. First, I barely believed I could…
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Career Growth & Advice, Hiring, Leadership, Q&A, ScaleWhy did Jason M. Lemkin change his point of view on the value of a COO for an early stage startup?
I try to work with (and invest in) CEOs that are better than me. I found, when I was a SaaS CEO, that the CEOs that complained about needed a…
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Career Growth & Advice, Growth, Leadership, Q&AHow much time does Jason Lemkin spend answering questions on Quora?
I try to spend about 20 minutes a day. I really enjoy writing on focused questions, it sharpens the mind and more specifically, helps me collect and “succinct-ify” my thoughts…
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Career Growth & Advice, Growth, Q&A, Sales, Sales StrategyIs Salesforce good for startups?
The one thing I do strongly recommend is letting each VP you hire pick her core tools and system of record. Forcing a VP of Sales to use a CRM…
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Where do Y Combinator founders stay while in the program?
If you are in B2B/SaaS, you’re welcome to work from the 18,000 sq ft SaaStr CSS in SF/SOMA. A bunch from the last batch did, all of whom got funded…
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Career Growth & Advice, Early, Featured Q&A, Q&A, Sales, Sales StrategyWhat is the best piece of advice on closing deals for a new, inexperienced salesman?
Add value. Most new salespeople focus a lot on the transaction. What’s your budget? Do you need a discount? How big a discount? Can I give you a bigger discount?…
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As an early employee, I own a part of a startup that’s about to IPO. These shares constitutes almost all of my wealth. As an aspiring conservative value investor of age 30, how much and at what rate should I sell off my shares after the IPO?
Goodness. Congratulations on the IPO! But what and how to sell is really a tough one. If you’d sold shares in almost any SaaS/Cloud IPO in the past 7 years,…
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Q&AHow will the proliferation of micro funds led by first-time investors change the early-stage funding landscape?
There are 500+ new sub $200m funds raised since 2011, and my guess is 200+ in the past 2.5 years: VC funds at / below $200M in size (new funds…
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What was your first entrepreneurial adventure? What was your last? Which did you enjoy the most and why?
My first entrepreneurial adventure was in the crazy days of Web 1.0: I joined one of my clients as a Director of Corporate Development in 1998. This was my first…
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Fundraising, Growth, Leadership, Q&ADo venture capitalists use Docsend when sending fundraising pitches to LPs?
I didn’t when I raised my first fund. I was in Sell mode. I wanted to make it as easy as possible for the LPs to buy. I sent a…
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Career Growth & Advice, Featured Q&A, Growth, Hiring, Leadership, Q&AWhat is the difference between running a 10 person startup and a 100 person startup?
The biggest structural difference is you have to hire all the VPs by employee 50–100. You won’t be able to scale this far without a full management team — VPs…
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What are some strategies for having new clients sign up for all their users rather than 1 or 2 users for a SaaS product?
Raj Khera’s list above/below is a great one and I can’t add any more value to it. Just one meta-learning: guide your customers to buying the right edition for them….
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Career Growth & Advice, Compensation, Early, Leadership, Q&AFor an Internet startup that secures, say $15m, in Series A funding, how much would the founders typically be drawing as salary?
In the Bay Area, $1X0,000. Once you raise $5m+ it’s time to pay the founders the low or middle end of “normal”. Founders may have different views of which end…
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Career Growth & Advice, Growth, Leadership, Q&A, Sales StrategyFor enterprise and mid-market SaaS, is there a recognizable turning point or do you just slowly realize that your sales and marketing are working?
For me, the turning point for knowing enterprise sales is working is when you get the third one of a category. It took us 18 months to close Google, then…
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Career Growth & Advice, Early, Leadership, Q&AWhat is life like as an entrepreneur and how does one overcome stage fright?
Don’t worry about stage fright. You’ll get over it. I remember the very first time I had to present to a Fancy Board Meeting. I wasn’t a founder yet, but…
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Career Growth & Advice, Customer Success, Customer Success, Growth, Q&AWhat is a SaaS company cancellation policy on yearly contracts?
The simple answer “of course” in that yearly contracts can’t be cancelled — per se. That’s the whole point of whatever explicit or implicit discount you give for doing a…
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Career Growth & Advice, Company Culture, Growth, Leadership, Q&ADoes a CEO have the right to fire an employee down the chain?
Of course. As you scale, you’ll have more formal processes here and in particular, around who and how to terminate an employee. Get a great HR professional on board as…
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Career Growth & Advice, Early, Hiring, Leadership, Q&AHow much easier is hiring when you are venture backed?
It’s always easier to hire when you have a brand. Once your company itself has and is itself a brand, it won’t matter. It doesn’t matter for hiring who invested…
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Why do some startups choose not to sell to other companies, and instead they go for an IPO?
I was just with a founder who owns 40% of his startup. He just turned down an offer for $500,000,000 to sell his startup to a public company. He is…
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At a $20B valuation, is WeWork overvalued?
Well, goodness since this question was asked WeWork is now worth $20 billion! + WeWork’s $20 Billion Office Party: The Crazy Bet That Could Change How The World Does Business…
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Career Growth & Advice, Customer Success, Customer Success, Growth, Q&A, Sales StrategyIn software sales, which is better: account executive (new business, fewer accounts, and outbound) or account management (existing account growth and revenue analysis)?
“Better” is hard to say but what is clear is that the Account Management role in SaaS is a much more fluid, in transition role. In recurring revenue, the sale…
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Popular Q&A
What is the best piece of advice on closing deals for a new, inexperienced salesman?
Add value. Most new salespeople focus a lot on the transaction. What’s your budget? Do you need a discount? How big a discount? Can I give you a bigger discount? What questions do you have? If I give you an even bigger discount, can you sign right now? Your discount...
What is the difference between running a 10 person startup and a 100 person startup?
The biggest structural difference is you have to hire all the VPs by employee 50–100. You won’t be able to scale this far without a full management team — VPs of Sales, Marketing, Product, Engineering, Customer Success at least. But the toughest personal challenge for...
What were aspects of your startup that were easier than you anticipated?
The part I didn’t originally get was how relatively easy is it to grow exising accounts and account size if your customers are happy. We segmented customer retention by Small, Medium and Large accounts after about 24 months and saw a pattern that I now know is fairly...
What should B2B SaaS companies do to ensure the success of their customers and reduce churn?
I know this sounds overly simple, but the answer is: Measure it. Set goals to improve it. Pay people to improve it. Too many start-ups don’t even know their CSAT and NPS. Too many start-ups don’t even visit their customers in person. Too many start-ups don’t know why...
What are some rookie mistakes founders make during VC meetings?
A few that are easy to fix: Not standing (when you present to > 2–3 folks). When you stand, you present better. Period. Standing turns you into the center of the audience, into the owner, the presenter. Sitting is great for a small convo, but sucks all the energy out...
How should I design sales reps compensation plans for my SaaS company at $10kMRR?
Figuring out your very first sales comp plan when you don’t have a repeatable process or much revenue is confusing. I was exactly in the place you were (first rep at $10k MRR) and everyone faces some similar challenges: There’s no way this early you can expect a rep...
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