SaaStr

FEBRUARY 19, 2024

And in fact, the product was already in decline by the time the CEO took $100m+ out. In fact, when we sold EchoSign to Adobe, we had a second offer than was worse for the founders, but better for the investors. I advocated we take that offer, even though I’d personally make millions less. Do founders now come first?

Trust 91

Trust Up-sell Closing Sell 91

Martech

APRIL 5, 2023

When times get tough, marketing budgets get cut. We also know businesses that keep investing in email marketing are better off when the economy improves. We also know businesses that keep investing in email marketing are better off when the economy improves. Are we in a recession or not?

Profit margin 126

Profit margin Objectives and Key Results A/B testing Strategic planning 126

SaaStr

SEPTEMBER 20, 2022

First, it’s tough to be truly fired if you control the majority of the board, voting shares, et c. So the more rounds you raise, the less it’s really up to you who the CEO is. The thing is, the last thing 98% of boards want to do is fire a CEO, and most especially in an earlier-stage startup. Missing a quarter is tough.

Start-ups 137

Start-ups Follow-up Trust Meeting 137

SaaStr

JANUARY 18, 2024

Dear SaaStr: What Are The Most “Evil” Things That VCs Do? VCs really do want you to be a big success. So really, the ‘worst’ things VCs do are simply around incentive dis-alignments. If you want to do anything else, you get misaligned, at least partially. Bridge rounds are tough to predict.

Price 92

Price Up-sell Growth Engineering 92

Iannarino

AUGUST 8, 2021

Less than half of salespeople reach their quota and more than half of buyers don’t change, evidence that what we’re doing isn’t working. They underestimate how difficult it is to create change, often doing too little to create an environment in which they can decide and move forward. The deadline for my fourth book is looming.

Intrinsic 328

Intrinsic Quota Clients B2B 328

SaaStr

AUGUST 24, 2022

Times were good then, and Toast was worth $24B. And yet, the markets are tough today, and Toast is now worth less than $10 Billion, despite executing admirably. As reps get better at selling in a new territory, efficiency and productivity. So we took a look at Toast just after it IPO’d. Fast forward to today.

Territory 115

Territory Referrals Growth Price 115

SaaStr

AUGUST 17, 2020

Here’s my list of the best golden advice I was given as a first-time — and second-time — CEO: Manage People — In General, and Earlier. They’ll see where you could improve in real-time. Take this real-time feedback and leverage it and act on it immediately. This is tough to do right for most of us.

Growth 145

Growth Pitch Closing Engineering 145

Partners in Excellence

FEBRUARY 15, 2024

They are probably using their time very well and are both effective and efficient. And, because of the way they work and their ambitions, they probably don’t have a lot of spare time. Stated differently, they are the people that probably don’t have the time to absorb more work! They become overloaded and overwhelmed.

Start-ups 101

Start-ups Up-sell Sell Product 101

SaaStr

JUNE 17, 2023

Market Fluctuations in 2023 Recent times have seen changes in the SaaS landscape, with market fluctuation being an expected outcome. Jason emphasizes that those who embraced change rather than resisting it were able to weather the storm much better. One such deal that Jason points out was Salesloft’s $2.5

Growth 85

Growth E-commerce Profit margin Strategize 85

SaaStr

NOVEMBER 4, 2022

You have to move fast and break things, but if the pit in your stomach says, “Maybe don’t do that,” — slow that decision down. Even when cash is tight, paying an extra $20k a year or more for a resource that is 2x-5x better is the best investment you will ever make. Don’t charge less to get the ball rolling. Charge more.

Growth 118

Growth Start-ups Customers Product 118

SaaStr

SEPTEMBER 13, 2023

That pond is stocked with new opportunities that will get fished out over time. That pond is stocked with new opportunities that will get fished out over time. Co-pilots — Co-pilots are where startups and founders can do new things that big companies won’t go after. It’s tough for investors. Of course, you can.

Finance 86

Finance Up-sell Contract B2B 86

SaaStr

FEBRUARY 3, 2021

Being the first salesperson into a start-up in a rewarding — but very tough job: Your Founder Boss likely will never have managed a salesperson before. She likely won’t know what you are supposed to do 40+ hours a week. Your Founder Boss may have strong views on what you should be doing. Which may be wrong. It’s too early.

Quota 106

Quota A/B testing Sales Up-sell 106

SaaStr

APRIL 17, 2024

But then growth flatlined for a couple of years, and it was time to talk about selling. How do these exits happen? Where do they come from? Why Do Offers Come? Your Fundraising Valuations Matter The last thing you want to do as a company is put yourself in a position where you can’t get the offer you want.

Sell 65

Sell Negotiate Up-sell Price 65

SaaStr

JANUARY 19, 2023

So the other day Colin Cadmus, who was VP of Sales at Aircall, summarized a career question I’ve thought about many times over the past 10+ years. If you are a great AE, a great sales exec … I know you might want “more” … but is it really better to be a VP of Sales? But less stress.

Sales 99

Sales Promote Start-ups Closing 99

Search Engine Land

NOVEMBER 30, 2023

Over the years, I’ve seen many agencies struggle and even shut down – including long-time players and heavily funded startups. Ideally, your top client should represent 10% or less of your business. But in stable times, you want to be good at saying “no” to work you’re less skilled in or that is less profitable.

Contract 106

Contract Clients Pitch Growth 106

SaaStr

APRIL 5, 2022

This is less common, but when it happens, it’s really rough. Do not blindly believe you can raise another round. Do not believe it will be easy just because you see “worse” companies raising rounds on TechCrunch. You’ll almost always end up having been better have never made the hire. Test the market. Transparency.

Engineering 96

Engineering Sales 96

SaaStr

JUNE 16, 2023

It’s tough, but it’s part of the circle of life. In the teammate case, I made the folks leaving feel guilty—“How can you do this?” When a teammate leaves, my only reaction is (1) thank you for what you’ve done here, (2) congratulations on what’s next and (3) what can we learn to continue to get better. Sometimes, it’s worked.

Clients 84

Clients Meeting Process 84

STAR Results

MARCH 25, 2021

Your market value appreciates as you become a better leader and have a large professional network. As a former sales executive , I was always in a tough spot. Although I cognitively understood the importance of investing in my own development and the advantages of networking, I always found myself too busy to do either.

Networking 169

Networking Finance Promote Meeting 169

SaaStr

MARCH 27, 2022

by the time the deal closed, we IPO’d … and then our acquirer went bankrupt. It was tough to recover from that. In fact, we were able to do the impossible. But when after that you know you should do it — just do it. This can be hard. I lost $12,000,000 on paper in 12 months, and it went to $0.

Trust 144

Trust Start-ups Growth Pitch 144

SaaStr

MARCH 6, 2021

One privilege I get as part of mentoring and investing in a few dozen startups is a chance to work with first-time managers. The reality is, most start-ups are better off with a Stretch VP than a Never Did It But Has a Great LinkedIn VP. We all need mentors, but especially, first-time managers. Do Weekly 1-on-1s.

Trust 141

Trust Start-ups Engineering Conversion 141

SaaStr

MARCH 20, 2021

Strong salespeople fail all the time in new roles. Good reps, that could otherwise do well, and have in the past. Why do good reps fail at a new role? A quick checklist to help you pick better: It’s important first to understand, do you need to be in an environment with lots of training, systems, process, and micromanagement?

Quota 136

Quota Niche Price Up-sell 136

SaaStr

JULY 17, 2023

A few objections reps think they can overcome … that they can’t: We literally do not need this product now. There’s the classic rule that only about 10% of prospects are truly in-market at any given time, and that’s about right in my experience. Too many reps do too many lame cadences and break things. Priorities do change.

Contract 83

Contract Pitch Gaming Start-ups 83

SaaStr

APRIL 2, 2021

We’ve hit some of these points before, but what are the Top 10 things I’d tell myself to do better, if I could go back in time? You have to move fast and break things, but if the pit in your stomach says “maybe don’t do that” — slow that decision down. Don’t charge less to get the ball rolling.

Start-ups 130

Start-ups Customers Product Sales 130

SaaStr

JULY 10, 2022

Especially now in 2022, when venture capital again is scarcer, and more expensive, and far harder to close than it was during the go-go times for SaaS of 2021 and late 2020. How do you make sense of it all? SaaStr Rule of Start-up Success #108: Just Multiply Amount of Venture Capital Raised Times 10. the amount raised.

Price 143

Price Up-sell Growth Start-ups 143

SaaStr

DECEMBER 11, 2021

Recruiting is tough. I certainly don’t do it well enough. Let me share some learnings, and what I do now to force myself to be a better recruiter: Force yourself to interview 30 candidates for each VP position. Great things will happen if you do. First, you will budget a ton of time for recruiting.

Networking 102

Networking Clients Start-ups Meeting 102

SaaStr

SEPTEMBER 13, 2020

Recruiting is tough. I certainly don’t do it well enough. Let me share some learnings, and what I do now to force myself to be a better recruiter. And what I wish I’d done better as a SaaS CEO: Force yourself to interview 30 candidates for each VP position. Great things will happen if you do.

Networking 145

Networking Clients Closing Start-ups 145

SaaStr

OCTOBER 1, 2023

As part of that, the very way we build SaaS companies has changed multiple times. We’ve gone from somewhat efficient through 2018 or so, to less efficient into 2020, to incredibly inefficient in late 2020 and 2021, to layoffs seemingly everywhere in 2022, and now to Efficient Growth. So, so much change.

Trust 81

Trust Engineering Growth Start-ups 81

SaaStr

JANUARY 29, 2023

Sometimes it’s VP Sales (OK, often, this is the most common mishire — another post here on what a really great VPS can do for you, and how a poor one can wreck your company, coming). First, Most of Them Didn’t Actually Do It All. Second, If They Really Did Do It All – Why Would They Join You?

Start-ups 112

Start-ups Up-sell Meeting Closing 112

SaaStr

JULY 31, 2022

When I went to raise the Series A for my first start-up, NanoGram Devices, it was tough. When I went to raise the Series A for my first start-up, NanoGram Devices, it was tough. I was a first time founder and first time CEO in a unproven space, and in tough times (between Web 1.0 You’d hope not.

Contract 85

Contract Follow-up Meeting Closing 85

SaaStr

APRIL 23, 2020

Time Zones are tough on a full-day event. Byron Deeter of Bessemer used the Q+A to have an incredible session with Jeff Lawson of Twilio that in many ways was better than it would have been in a traditional 1-on-1 on stage. Q+A is tough to do well IRL. How do we bridge the gap? Default to 20 Minutes.

Presentation 125

Presentation Technology Technology Closing 125

SaaStr

DECEMBER 6, 2022

I just got back from Reinvent (Amazon’s big conference) and the booths were packed, the parties were full, and times were good. So to do more with not less, but not as much more as planned … everything is under new scrutiny. So to do more with not less, but not as much more as planned … everything is under new scrutiny.

Closing 88

Closing Growth Up-sell Product 88

Search Engine Land

JULY 7, 2023

Systemizing your business well can provide ample time and cost savings and potentially boost your sales. I’d go as far as to say that it’s tough to scale or grow meaningfully unless you have systems in place. You can manage your time better. Your customers get high-quality service every time. What is a system?

Follow-up 98

Follow-up Up-sell Start-ups Process 98

Search Engine Land

NOVEMBER 14, 2023

So, where do you begin with enhancing customer experience? Understanding conversion rate optimization Before delving into these behavioral nudges, let’s quickly set the stage for those less familiar with conversion rate optimization (CRO). Herding is the tendency of humans to follow what others are doing.

Conversion 115

Conversion Price B2C Manufacturing 115

Partners in Excellence

MARCH 22, 2024

But I never found it, so I stayed doing what I’d been doing. But over time it’s built in me a passion for this profession. I moved to Southern California right out of college, owning next to nothing and knowing even less. He and I share ideas about the state of selling and how we can drive improvement. I like ideas.

Sell 77

Sell Construction Finance Up-sell 77

SaaStr

NOVEMBER 2, 2021

Even when you haven’t worked there for the better part of a decade. Plus, she had recommended the company many times. We’d met her many times in person. Spend a little more time on existing customers, and a little less time on prospects and Hot Deals as CEO. Do it every month.

Customers 116

Customers Contract Launch Prospecting 116

Partners in Excellence

MAY 16, 2022

“ Still the question recurs ‘can we do better?’ They are always challenging themselves, their teams, and organizations with “Can We Do Better?” When things are bad, when we aren’t achieving our goals, it becomes, “We must do better!”

Construction 79

Construction Quota Pitch Campaign 79

Sales Hacker

JUNE 16, 2022

It’s been a tough couple of years, Sales Hackers. What do the changing market conditions mean for RevOps and sales? Q: How can you know it’s time to take measures against recession, such as pivot toward deal efficiency? Have their back (and tell them you do). And it’s about to get tougher. Here’s what they said.

GTM 91

GTM Pipeline Sales A/B testing 91