We've made 50+ videos over 10 years at Gainsight — but I've never been more fired up than for this one. 🔥
What would happen if Taylor Swift wrote a breakup song about a Unicorn Founder and a Venture Capitalist? 🦄
I proudly present to you "All Too Well (VC / Founder Version)"
Common reaction to a teammate resigning:
1. Why are you leaving?
2. How can we keep you?
3. Do you know you're going to regret it?
Alternate Golden Rule version:
1. Thank you for your service
2. Congratulations on your new job
3. What can we learn?
I can't count the number of days where I've had to go from:
A call with a teammate who is resigning to
A call to recruit someone new
A call with a client leaving to
A sales call
A call with an investor passing to
A VC pitch
Very few skills more important than bouncing back.
One of the cheapest and simplest career hacks is to be hyper-responsive. I've found some of the busiest leaders in the world are also the fastest to reply to emails.
Underrated skill: Being there for people when they need it.
My evolution as a leader:
Me in my 20s: "What's the playbook for this?"
Me in my 30s: "Here's the playbook for this."
Me in my 40s: "There is no playbook for this."
Every SaaS application pitch ever (including ours):
1. Your data is in lots of places
2. So you use spreadsheets
3. We bring it all together
4. Profit
Not a bad pitch!
If you intend to run your company for a long time, one key role as CEO becomes being the "historian."
Many people that work for you won't have the context of how your team got to where they are at - and of why things worked and didn't work. It's your job to remember the stories.
@EricNewcomer
My biggest worry is there are many other shoes to fall across many asset classes (not just crypto). As Buffett says "A rising tide floats all boats….. only when the tide goes out do you discover who's been swimming naked."
Every time I find myself struggling with a challenge or throwing myself a "pity party," I reread what I consider the greatest CEO blog post of all time - "Nobody Cares" by
@bhorowitz
:
TBH the amount of financial FOMO right now in the world (unicorns, SPACs, mega IPOs, Bitcoin, Tesla, megafunds, everyone raising their own fund, trillion dollar stocks... and now GameStop?) seems higher than at any point in my adult life. And that includes 2000 and 2008.
Every fancy restaurant meal for a vegetarian ever:
Waiter: "Let me tell you about the specials... sirloin... pork... lamb... bone-in... shank..." [5 minutes of meat]
Me: "Do you have any veg options?"
Waiter [clearly disappointed]: "We can steam some broccoli for you"
Lost a family member yesterday due to COVID.
Grieving as a group through videoconferencing is so brutal.
Feeling for the thousands of people worldwide going through this every day.
TBH I traveled nearly every week for the last ~20 years. I was always home for weekends and told myself "I'm not missing too much" since I'm very present Friday-Sunday.
TIL this year: I've been missing a ton. And I'm not going to go all the way back to the way things were.
The market for SaaS execs has truly reversed. The most interesting jobs in terms of upside are in public companies and PE-backed cos. There are certainly some VC-backed cos with upside (esp early stage) but working at an overfunded, under-ARRed unicorn is a tough sell for most.
Spoke to an entrepreneur the other day with this funding history:
Seed: Led by a hedge fund
Series A: Led by a growth fund
Series B: Led by an early-stage fund
That's some straight-up Benjamin Button stuff there... well done!
Very few no-brainer choices in business. But I'd say for SaaS companies, having a 1/31 fiscal year end (versus 12/31) is as close as it comes. At a minimum, your team gets a much happier holiday season!
It's easy to think of a "company" as one thing. Yet every day, teammates are in different parts of the journey. Some are burned out. Some are thriving. Some have hit the wall. Some just started. Some believe. Some no longer do. Seeing the individual humanity in a team is the job.
"You can't have a great culture and be remote-first."
A lot of people believe that. And maybe it's harder - I don't know.
All I know is Gainsight has been a work-from-anywhere company for a LONG time and is now the
#1
-rated company on Glassdoor.
You can make anything work IMO.
A big learning for me over 9 years running Gainsight:
As a CEO, you can never make enough spontaneous calls / texts / Slacks to your team thanking them for their work. They go a long way.
Had breakfast with the CEO of a fast-growing, VC-backed SaaS company today. His unprompted quote: "At our company, we never ring the gong when a customer buys. We only ring the gong at the renewal. We don't celebrate shelfware."
#CustomerSuccess
It’s interesting that most of the high growth SaaS companies who also have high FCF margins were bootstrapped early on (eg Zscaler, Atlassian, ZoomInfo)
Capital efficiency, like most sports, is easier to learn when you’re young!
I love remote work and all... but we closed our biggest deal in company history today... and I really want to high five someone... but our kids seem entirely unimpressed by our accomplishment.
2 years ago, I could challenge you to find one SaaS company that I didn't know. Since SaaS is a big chunk of our TAM, I'd met every one of them.
Now, for SaaS cos < 500 employees, at least 75% of the ones I hear about are for the first time.
SaaS is completely exploding 💣🔥🔥.
One of the value props of SaaS is that the tech automatically evolves.
As such, buyers should remember that they are buying roadmap - not just current state.
This is one of the biggest problems with building custom technology versus buying.
Internal roadmaps can't keep up.
I'm trying an experiment in internal meetings: Writing down anything I'm going to say in my notebook before I say it. I'm finding (1) it lets me listen more to others versus focusing on "my point" and (2) it helps me realize not everything that's thought needs to be said.
Took my first plane flight today since March 2020. Got all nostalgic going through the airport and even through the TSA line.
Then I tried United in flight WiFi again and my daydream ended.
As a leader, I sometimes feel like no matter what I do, I'm failing someone - whether a client, teammate, investor or family member. The trick is never giving up in caring about everything while not letting it eat you up inside. If anyone has learned "the trick," please teach me!
So honored to partner with
@Vista_Equity
to power the next phase of
#CustomerSuccess
. Huge validation of the impact of the CS community, as well as grit of the Gainsight team and alums. Working on the Unicorn 🦄 rap now…
Every Steeler fan secretly knows that this AB saga ends with Brown being signed by Belichick... and the Pats beating the Steelers in the AFC Championship for the 1000th time on a trick play touchdown pass to AB from an unretired Gronk.
I've spoken to enough SaaS CEOs to know this is a "thing"...
Zoom-date (noun): The specific date and time when you read the Zoom S-1 as a cloud exec and rethought all of your life's decisions.
I've seen compassionate and positive people join companies with negative cultures and have the worst brought out of them.
And I've seen supposedly negative people join positive cultures and totally transform into their best selves.
Cultures are powerful - for better and worse.
We have 6 teammates in Ukraine. I asked one of them what we can do to help. Her response:
"I don't know how to ask. But please support my country by continuing to hire Ukrainians because it's really important. Please send this message to Your friends in the Tech world."
🇺🇦
Some of you know that my dad is sadly going through serious health & memory issues. Impossibly hard stuff.
But this made me smile:
My mom reminded me last night that one of the first businesses he started in 1981 was called... wait for it... META INC.
He's the OG META (/Mehta)
Guess what SaaS stock is up 11.74% in the last 6 months while the broader $EMCLOUD cloud index is down 50.76%? $BOX
So proud of
@levie
and the team at Box. They've transformed the company into one that is sound for the long-term, while dodging many curveballs along the way.
I don't have many lessons for business that apply universally. Everything is situational.
But for me, one thing I always remind myself is:
You are a human first
And a business person second
So treat everyone (customers, employees, even competitors) as human beings first too.
Every software company (to their customers):
"Why would you build it yourself instead of using our product out-of-the-box? We're the experts."
Also, every software company (internally):
"Can we custom build something ourselves instead of using all of these outside vendors?"
So much to say about today's exciting news for us. But I'll answer the ? on everyone's mind...
What am I more excited about?
GS becoming a 🦄, etc. OR
Steelers being 10-0
I will say this is definitely the proudest day of my career...
But PIT has never been 10-0.
So I'm torn!
Just closed a huge deal. The champion made a big difference. None of that is interesting.
What is intriguing: he was in 2 cos previously where he couldn't buy (for a variety of reasons). But we stayed close.
Stay close to advocates - even across failed sales cycles & churns.
Can we all take a moment and give a virtual hug (or elbow bump?) to
@jasonlk
? I can only imagine how stressful the last few weeks have been for him and
@saastr
.
Jason has carried the SaaS industry on his back for years. Can't thank him and his team enough. Bi-Annual will be epic
Hung out with a fellow CEO today and we were refreshingly able to have a conversation that wasn't about "crushing it" but was instead much more real about our day-to-day struggles, fears and worries. Life feels vivid and powerful when people are vulnerable with each other.
Me years ago, as a first-time CEO, talking to other CEOs:
"Let me tell you how we're crushing it" (with almost no revenue)
Me now, with a real business, talking to other CEOs:
Just my POV but I think companies put too much of the blame for execution issues on individual contributors and not enough on leaders. Great leaders make ICs 10X better. We need 10X leaders.
Also "to those who much is given, much is expected."
Many of us in tech did well business-wise in 2020.
I'm reminded of this quote from Michael Lewis, Moneyball author, from his 2012 Princeton commencement address.
This
@bhorowitz
classic post should be required reading for exec teams going into 2023:
"All the mental energy that you use to elaborate your misery would be far better used trying to find the one, seemingly impossible way out of your current mess."
Spoke to a Product Manager today who decided to move into the
#CustomerSuccess
profession. I asked them why they are switching.
They said "It's so clear that the future of technology isn't just about building products - it's about making sure customers get value."
Spoke to an entrepreneur today who is raising 💰. Maybe I'll get kicked out of the CEO club for saying this, but I have empathy for investors these days.
Every sector (VC, PE, growth, Tiger, etc.) is competing in every deal. I can only imagine how hard it is to differentiate.
Tough reality of the biz world is that many ppl will disappoint you. They won't live up to promises. They will ghost you. They will talk about you behind your back.
For me, the only reaction that works long-term is to use each instance as motivation to treat ppl that much better
SaaS sales deck paradox:
Marketing teams create beautiful, 20-slide sales decks
Yet salespeople know buyers have a short attention span before they say "let's get to the demo" and only want 3-5 slides max
So much time is wasted making slides that are never presented
Airpods are amazing in so many ways. But perhaps the most innovative part of the design is how Apple figured out how to make the Airpods fly like 100 feet from the case when you drop it.
This is one of the saddest things I've ever read. I'm grateful to the author for sharing his tragic story and giving us a chance to remember how precious our time with those we love really is.
We got a 10/10 NPS from a client. Not tweetworthy.
But check her NPS over the last 2 years:
6/2019: 1/10
12/2019: 5/10
12/2020: 8/10
6/2021: 10/10
She went from being a critic to now saying our Horizon UI is "truly breathtaking."
❤️ Progress
P.S. I still read all surveys.
I was shocked when I read that a typical CEO spends 5.6% of their time with clients. I looked into my percentage (17%). I love meeting with clients, but it takes a process to make it work. I broke down the mechanisms I use to meet as many clients as I can.
Zoom level 100 achievement locked:
Matching virtual background and outfit
Boldly going where no videoconference attendee has gone before.
(BTW any true Star Trek fan knows red shirts never make it back, but I plan to buck the trend...)
Prince Harry receiving his first auto-SDR email:
"I noticed your job as PRINCE OF ENGLAND at BetterUp and was wondering if you had 15 minutes to discuss..."
I have heard a number of folks state that "great culture" is about "finding great people." I personally see it differently. I've found the best cultures bring greatness out of everyone. Most people have so much potential inside them and companies never get to see it.
Jokes aside, I love California. It's the only place in the world where I moderately feel at home and like I fit in - like I belong.
I don't want to be anywhere else.
So this is all breaking my heart.
Churn calculations (including the ones we use) all have a fundamental flaw. They track the lost CURRENT ARR. Yet perhaps the biggest impact of churn (especially with large clients) is the lost FUTURE expansion dollars.
So churn is an even bigger deal than people realize.
Someone asked me today what I’d tell my earlier CEO self at the time of the launch of Gainsight. I have few real lessons and believe the path is only the path. But I had one thing:
It doesn’t get easier - ever.
But it does get more meaningful.
.
@bhorowitz
's essay "Nobody Cares" NEVER gets old. And as we head into what looks like an incredibly-choppy time for tech, it's never been more relevant.
My advice to myself and to other leaders: Read it every week...
My parents moved to the Bay Area a while back to be near us. Given current circumstances, they've been sheltered alone in their retirement condo.
As such, it was really nice to see their faces today (way more than six feet apart) and take a social distance-friendly selfie!
I am on cloud 9 after
@SaaStrAnnual
today. So inspired by the entrepreneurial energy buzzing through San Mateo. And so grateful for the fist bumps and smiles of an IRL event!
Massive thanks to
@jasonlk
@saastr
for being the ultimate community builder. We all owe him so much!
People talk about "war time CEO" & "peace time CEO" a lot. I think it's a useful framework.
That being said, I'm seeing a third kind of leadership model showing up in this crisis where execs are considering the human impact of their decisions more than ever.
Human-first CEO.
Extraordinary leadership from CEO of Outback Steakhouse (Bloomin' Brands):
Sales down ~60%
No furloughs or layoffs (90,000 employees)
CEO & board pay cut to 0
Free meals for staff
"Our priorities have centered on taking care of our people and serving food in a safe environment"
Check out your text messages from a year ago...
One of mine to a friend on 3/11/2020:
Me: "Sorry, can't do dinner tonight. We're locking down for a bit as a family given COVID. Let's get together in a few weeks. Worst case - we'll see each other in April."
However you and your company act during this crisis ARE your values. Values aren't what we do on our best days. They are how we react on our toughest ones.
My 12 year old daughter is doing a school project & chose to research gender-related pay equity. She independently found a video by
@Benioff
talking about it & was super inspired. So cool to see the impact that purposeful leaders can have.
Qualifying phrases like "to be honest," "candidly" and "frankly" often do more harm than good. They put the listener on the defensive and also imply that your usual statements aren't honest/candid/frank.
It's been an important learning for me, TBH. 🤣🤣🤣
Don't you dare apologize for your kids coming onto the videoconference call or your dogs barking.
We are all human beings getting through this together. We are inspired by the way you are finding your own balance.
Being honest, seeing the kids & pets is the best part of my day
Our eldest graduated from high school last night.
Now I'm headed to my 25th year college reunion.
"Life moves pretty fast. If you don't stop and look around once in a while, you could miss it."
One of my favorite parts of the end of the fiscal year is calling individual contributors who exceeded their quota/goals to congratulate them. As your company gets bigger, spontaneous 1-1 phone calls (old school, I know!) go a long way.
@JenMReason
“Tomorrow and tomorrow and tomorrow creeps in this petty pace from day to day”
(I trust you’ll understand the reference to another Scottish tragedy without having to name the play) - sorry slipped into Hamilton!
Saturday was my 10-year anniversary of leading
@GainsightHQ
. That feels weird to write.
I made lots of mistakes over my first decade, but I'm grateful for the things we got right (mostly due to me listening to other, wiser people!). Here are 10 things that seemed to work.🧵
I'm all about
#CustomerSuccess
(in case that's not obvious!). But as a CEO, if you find out that a customer is being abusive to one of your team members, you need to stand up for your teammate, even if it means losing the client.
So lucky to be on the field with this team for by far our best quarter in company history. Our amazing clients, teammates and shareholders made this all possible.
Startups are hard sometimes so you really need to celebrate the great days. Today was one of the best ever for us.
People talk a lot about schools preparing students for the future of work. In that vein, I suggest a mandatory class on installing video conferencing software, since that is at least 50% of the workday.