I’m no @HarryStebbings, but having done a lot of interviews of busy decacorn and unicorn CEOs, a few tips for podcasts + interviews:

#1. You’ll be surprised who you can get via outbound — >if< the pitch is strong.

Really research guest you want & find a way to appeal to them
#2. Don’t make VIP guests, or any experienced guest, do a prep call.

But do ask if they want to do one.

Some folks will decline the invite if there is too much prep work (e.g., me). Others will appreciate it, especially for top events, podcasts, etc.
#3. Send the list of questions you have for the guest over 3+ days in advance.

I do it in a Google Doc so they can make edits, add stuff.

Everyone reads it. Everyone. So they prep that way.
#4. For a while, folks didn’t really want to hear “early days” stories. Unicorns used to rare, & folks wanted to hear what that was like.

But the pendulum has swung back. With 500+ unicorns, attendees now believe they can do it.

So they want to hear how it all got going.
#5. It’s OK to ask the same question to a CEO / guest they’ve been asked 100 times.

As CEOs, we’re used to telling certain stories again and again.

But try to get a new angle out of it. They often sparkle when there’s a new insight to tell on a well-told story.
A few other tiny tips:

- Schedule it whenever it works for them, not you.
- Most top CEOs show up early. So ask them when they log on if there are 1 or 2 things they really want to talk about. They’re usually excited about those things = good content.
- Bad audio is fatal.
Lastly, and it’s a shame no one does this:

Send all your guests a video / audio link and file of the interview, and tell them to use it wherever & however they want

They almost always at least put it up on their blog, etc.

Free extra distro.

But no one does this.
Here were our top 10 most popular digital sessions of 2020. You can get a really good sense of what really works from them:

saastr.com/500000-tuned-i…

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More from @jasonlk

4 Jan
Twilio has long been one of our favorite companies at SaaStr, combining B2D + B2B, long-tail, SMB + enterprise, and much more

They are >still< growing 52% at $2B+ in ARR

Here are 5 Interesting Learnings from Twilio:
#1. The Top 10 Customers at Twilio have been 15%-20% of its revenue for years.

Yet Twilio has 200,000+ active accounts.

So they work hard to make a long tail AND big whales work together in 1 company

You don't have to choose. Don't let folks force you to.
#2. NRR has come down a bit from 140%-150% around the IPO, but is still world-class at 137%.

It's a great reminder NRR does not have to come down as you scale

Accounts can remain less than fully penetrated for many, many years

All the way to $2B+ in ARR
Read 8 tweets
3 Jan
Bill.com is one of my favorite SaaS stories

We run SaaStr on it & it makes my life 10x easier

It's a great 2nd-time founder story. CEO sold first co for $150m & then did it again. It was hard. But today runs an $11b leader

Let's look at 5 Interesting Learnings:
#1. It can take a long time with SMBs. Bill.com has 100,000+ SMB customers ... and it took them 14 years to get to IPO.

Growth often was slow. But it >accelerated< at $100m ARR< to 56% YoY.
#2. Bill.com had 110% NRR at IPO and 121% today, and 86% logo / customer retention.

So again, you can get to 100%+ NRR even with the tiniest of customers ... IF they really need you.

They run their businesses on Bill.com.
Read 9 tweets
3 Jan
The “hybrid office” is going to be a lot of work to do right

Many folks are going to want to retain most of benefits from WFH ... along with the social and collaborative parts of the IRL office

Have our cake and eat it too. I know I do.

This will be much more work than before
Many costs will actually increase. For example, even now, we are maintaining more office space than before so everyone has their place.

“Hotelling” really doesn’t work that great for many roles. Not every job is well done just “plugging in” to a random desk.
Also, distributed team members can no longer be second-class citizens. That day is long gone.

We’ll all now have to act “distributed-first” even in IRL meetings, etc. which change how we all work, force us to be more organized, and use tools like Zoom almost as much as now.
Read 4 tweets
2 Jan
Asana is the tool we all know even if we don't use it ourselves. With that famous B2C CEO that decided to do SaaS next.

It's crossed $250,000,000 in ARR and is starting to march upmarket

Here are 5 Interesting Learnings from Asana at $250M ARR:
#1. Asana, like Slack, has self-service roots. But now, 40% of its customers are closed by the sales team, trending to 50%.

Asana is now planning to double the size of its sales team in 2020
#2. Asana has 115% NRR overall, but it's the segmentation that's interesting.

140% NRR for $50k+ customers
125% NRR for $5k-$50k customers
100% or so NRR for < $5k customers

Given it still skews 60% SMB, this is consistent with other market leaders like Zendesk, etc
Read 9 tweets
1 Jan
Salesforce buying Slack for $28B must have seemed like one of the oddest combos of 2020

But it wasn't. Slack had already become quite an enterprise solution ... without leaving behind its freemium and developer/product-centric roots.

5 Interesting Learnings from Slack at IPO:
#1. By the time Slack IPO'd, freemium had become more of a lead-gen tool that a revenue stream.

Only 8% of Slack's revenue was from Free-to-Paid at IPO. Just 8%.
#2. By IPO, Slack already had 575+ $100k+ ACV customers.

And $100k+ deals were already 40%+ of Slack's revenue at IPO.

That was up from just 22% enterprise 2 years earlier.
Read 9 tweets
31 Dec 20
Both Shopify and Zoom have rocketed to $100B+ market caps this year

Zoom has perhaps gotten more attention, but Shopify has undergone at least as much change, and has exploded to a $3.2B+ ARR run-rate since Covid (!)

Let's take a look at 5 Interesting Learnings from Shopify:
#1. Shopify moved from a 14-day free trial to a 90-day one during Covid ... and conversions went >up<

The lesson? Let the customer buy the way they want, and need, to buy

And often making a free product >freer< can work

Don't always tighten the gates
#2. "SaaS" can be consumption-based. It doesn't even have to be primarily subscription-based anymore.

Shopify's subscriptions grew 48% this year ... but its payments revenue grew 132%, and now is much larger than the subscription side

Subscriptions fuel payment revenue now.
Read 7 tweets

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