SaaStr

SEPTEMBER 12, 2022

Dear SaaStr: What Are the Danger Signs a Startup Isn’t Going to Work Out? It’s more about things I worry about after : Founders’ understanding of market doesn’t get deeper. I really worry when 9–12 months later, the founders do not understand their market better. When others fly. When the year plan is at risk.

Gaming 110

Gaming Up-sell Sell Customers 110

SaaStr

JANUARY 10, 2024

When you get everyone on the leadership team in a room to come up with the best ideas, those people take ownership of the ideas. Yes, marketing has to do all those things, but I think if marketing is going to do its job well, it has to be involved in the company core, the story for why does this company or product exist?

Pipeline 98

Pipeline Growth Strategize Start-ups 98

SaaStr

SEPTEMBER 20, 2022

First, it’s tough to be truly fired if you control the majority of the board, voting shares, et c. And everyone knows startups are tough, and have ups-and-down. Where boards get so nervous as to want a fire a CEO is when the bad news is a big surprise. Missing a quarter is tough. We saw this live with Uber.

Start-ups 138

Start-ups Follow-up Trust Meeting 138

Cerebral Selling

MARCH 4, 2024

What Got You Here, Won’t Get You There Most sales leaders end up in their roles because they were top-performing reps. The good news is, when it comes to knowing what it takes to be a great sales leader, I’m about to show you that you already know the answer! helped me through a tough time in my life.” How massive?

Cross-sell 130

Cross-sell Sales Referrals Launch 130

SaaStr

NOVEMBER 2, 2023

So I thought I’d come back to the classic topic and make a list of the Top 10 Mistakes I See Founders Make When Hiring a VP of Sales: #1. At least get close. So many VPs of Sales disagree with me here — at least at first when I make the point. Ask who those 2-3 are. Or puts in the effort to do so.

Process 92

Process Sales Up-sell Quota 92

SaaStr

MAY 3, 2024

investor in Algolia, and CEO Bernadette Nixon came to SaaStr Annual with CRO Michelle Adams to talk about a critical but under-discussed topic: How to Get CEOs and CROs trulys on the same page. #2. We’re fortunate that over the years so many of their founders and CEOs have spoken at SaaStr Annual and Europa !

Growth 80

Growth Start-ups Customers Sales 80

SaaStr

DECEMBER 4, 2022

Your family will never really understand what you go through as a founder. And what we know now for sure, that we always still knew anyway, is that it both (x) takes 7-10 years to Go Big in SaaS , (y) and it probably takes 12-20 years to build something iconic. To go long. Get 1 or 2 great mentors. It’s tough.

Consult 119

Consult Growth Presentation Start-ups 119

SaaStr

JUNE 26, 2023

One thing we’ve talked a ton about at SaaStr since inception is the power of going global as early as you have customer pull in other geographies. Some examples: HubSpot gets 54% of its revenue from outside the U.S. Asana gets 39% of its revenue from outside the U.S. Monday gets 47% of its revenue from outside the U.S.

Growth 115

Growth Territory B2B Sell 115

Hubspot

FEBRUARY 27, 2024

It can be tough to know how to reschedule a meeting appropriately and effectively. It can be tough to know how to reschedule a meeting appropriately and effectively. How to Reschedule a Meeting Professionally When should I reschedule a meeting? When rescheduling, be respectful of your fellow stakeholders' time.

Meeting 60

Meeting Contact Follow-up Start-ups 60

SaaStr

MARCH 22, 2021

I’ll make a short list: When you don’t know what to do — go visit your customers. Don’t let the good ones go. Sometimes, your best teammates just need to move on, found their own company, get that VP role somewhere else, etc. Don’t let the good ones go. Find a great mentor — for the tough decisions.

Gaming 118

Gaming Promote Presentation Customers 118

SaaStr

AUGUST 21, 2020

But let me share what I’ve learned are signs an entrepreneur likely won’t be going for it / won’t build something big. But selling your company for $20m-$30m isn’t consistent with raising VC capital or going big. You have to carry yourself as the CEO you want to be in 2–3 years, and act with that level of professionalism.

B2B 132

B2B Up-sell Start-ups Closing 132

Iannarino

JULY 10, 2021

But the advice here is designed to be helpful in many client conversations, not just the tough ones. The very first thing you should do when preparing for a client conversation is to know your outcome—your goal for the conversation. You increase your ability to succeed in client conversations when you have a target outcome.

Clients 284

Clients Conversion Up-sell Start-ups 284

Partners in Excellence

NOVEMBER 9, 2023

We want to get a desired outcome without doing all the work one would normally have to do to achieve that outcome. I continue to imagine, “Wouldn’t it be great if I could achieve my desired level of fitness, without having to go to the gym for an hour every day! ” (I did get a lot of value from the book.)

Pipeline 129

Pipeline Drivers/motivators Technology Technology 129

Spiro Technologies

DECEMBER 29, 2022

When the calls and meetings are over and salespeople are left to their own devices, they can do things without the watchful eye of their prospects, customers, coworkers, and importantly, sales managers. Here are 10 of the things salespeople really do when no one is watching: 1. Blast music to get pumped up on the way to work.

Commission 110

Commission Appointment Represent Clients 110

SaaStr

SEPTEMBER 27, 2023

Some of us can go the distance as solo founders, and others of us can find a great co-founder, or perhaps a COO … later. But most of us can’t really get it off the ground without a strong co-founder. Wait too long, you’ll never get there. It’s hard enough to get 2, 5, 10 customers. This challenge never ends.

Niche 101

Niche Engineering Start-ups Growth 101

SaaStr

AUGUST 18, 2023

Toast dominates the restaurant POS space but its model has some inherent challenges in getting to positive operating margins: it sells to SMBs with a sales-driven model (harder), it has high hardware costs that it loses money on, and it has high services costs onboarding these small customers. In many cases, for the first time ever.

Growth 76

Growth Service Sell Sales 76

Hubspot

AUGUST 14, 2023

Salespeople frequently undermine their chance of winning sales when they allow value leaks — instances where your email, proposal, word choice, presentation, or body language diminishes the perceived value of your solution — to creep into their sales processes. Why do value leaks occur? Value leaks are often the byproduct of previous losses.

Closing 88

Closing Hospitality Negotiate Price 88

Cerebral Selling

AUGUST 8, 2022

In July 2022, over 30,000 tech workers were let go. Since March 2020, the world has been in a state of constant change and uncertainty. We’ve seen the splintering of society with the pandemic, politics, issues of social injustice, the great resignation, and now, inflation and recession. Create certainty where you can.

Sales 199

Sales Contract Clients Quota 199

Heinz Marketing

NOVEMBER 14, 2023

By Maria Geokezas , Chief Operating Officer at Heinz Marketing It’s no secret marketing and sales are equally critical to your go-to-market success. But sometimes, things go off track, and marketing and sales operate in their own silos causing them to be misaligned in the way they attract and acquire new customers.

Go To Market 119

Go To Market Lead generation Sales Meeting 119

Sales Pop!

MAY 2, 2024

Inflation affects every aspect of the economy, but there are steps you can take to minimize adverse effects and continue growing despite tough times. 1 – Get Better Insurance Many business owners know they need better insurance but they’re not sure how to go about getting it. It doesn’t have to be a mystery.

Profit margin 52

Profit margin Price Growth Service 52

SaaStr

AUGUST 1, 2023

So what the heck happened in 2022 and into 1H’23, when SaaS unicorns could go from 100%+ growth to 0% in 12 months? You get all the VPs into a room, and you tell them to make a list. Everyone knows the 1-2 apps they don’t really need (or frankly, the 1-2 employees they don’t really need). The list goes on.

Finance 81

Finance Growth Closing Customers 81

SaaStr

AUGUST 17, 2020

This is tough to do right for most of us. This is tough to do right for most of us. Especially as founders, we tend to go heads-down after a win, because it’s just one step in a bigger plan. Get on a Jet. Go visit your customers, partners, and prospects. Get more advice. Go All-In on Them. More here.

Growth 144

Growth Pitch Closing Engineering 144

SaaStr

NOVEMBER 4, 2022

Dear SaaStr: As a VC, if you could go back to your operational experience (as part of a hyper-growth startup), then what would you remind yourself to take note of? My top list: Slow down big decisions — when you aren’t sure. My biggest mistakes were when I said roll the dice, but my gut wasn’t sure the downside risk was worth it.

Growth 117

Growth Start-ups Customers Product 117

Martech

APRIL 5, 2023

when a country’s gross domestic product falls in two consecutive business quarters). 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. Go beyond subject lines and button colors.

Profit margin 125

Profit margin Objectives and Key Results A/B testing Strategic planning 125

SaaStr

JUNE 22, 2023

Dear SaaStr: What do startup founders typically get wrong when starting a business? My list: Not committing to 24 months upfront to getting to Real Revenues and a Minimum Sellable Product. If you are willing to commit for 2 years to get to MSP and 7–10 years to get to Something Big … but your co-founder isn’t.

B2C 90

B2C B2B Up-sell Start-ups 90

SaaStr

MARCH 27, 2022

It was tough to recover from that. And even harder to think about Going Long. If you can get to $10m in ARR, growing 80-100% or more Year-over-Year, and have happy customers AND a good team … if … then you can’t be stopped. You can get to $20m, then $40m, then $100m in ARR. 3. Go For It.

Trust 144

Trust Start-ups Growth Pitch 144

Martech

AUGUST 22, 2023

Marketers certainly demonstrated their tenacity in navigating the unknown and getting things done. Marketers certainly demonstrated their tenacity in navigating the unknown and getting things done. It’s time to go back to strategy and let it lead tactics. We email marketers need to get back to that strategy-first approach.

Strategize 98

Strategize Start-ups Follow-up Campaign 98

Partners in Excellence

FEBRUARY 15, 2024

” They go on to say, “The easiest way to hit your goals is to give all the best opportunities to your top performers.!” Our B players are no longer getting high quality leads. At best, they get mediocre leads, and probably a lot more junk than they got before. You don’t want to be wasting your leads!”

Start-ups 109

Start-ups Up-sell Sell Product 109

SaaStr

FEBRUARY 1, 2023

Public stock prices go up and down, after all. The real problem is how venture capital works in practice — the nichey, quirky way private financings and investing works: VC investment is high-ish risk and you need to know when to just walk away. When a start-up is hot, it’s insanely easy to raise more money.

Price 100

Price Finance Start-ups Gaming 100

SaaStr

APRIL 4, 2022

Every VP of Sales knows around now, they are at risk of getting topped (someone hired above them) or even pushed out. Why Sales is a Tough Job. Just a few thoughts: *Have a CEO-VPS conversation about how far they can go. Do this once a quarter or at least 2-3 times a year. Even when last quarter was epic.

Sales 97

Sales Conversion Process 97

SaaStr

NOVEMBER 22, 2021

Every great VP of Sales has 1 or 2 folks that wants to follow them from their last role. Nothing gets better in 1 sales cycle. But you do need to see things get better. So let me tell you the #1 sign a VP of Sales just isn’t going to make it under any circumstance. It’s when they Hide from a Miss. Sales is tough.

Sales 97

Sales Meeting Follow-up Closing 97

SaaStr

AUGUST 31, 2022

Even with some sales cycles indeed getting a bit more challenging, especially for deals in the $500k-$1m range. But Wall Street seems OK with it, since operating margins are going up and the growth is epic. Jaw dropped in how Cloudflare just keeps the engine going, from revenue growth to NRR to GRR. No downturn, no slow down.

Growth 105

Growth Pipeline Engineering Customers 105

SaaStr

MAY 17, 2023

It’s built its way into an enterprise contact center leader and has now crossed $2 Billion in ARR, growing a mature but still steady 16%. Everyone from HubSpot to FreshWorks and more are just getting a lot more efficient, fast. #2. And while it’s not GAAP profitable, on a non-GAAP basis, its margins are way up to 17%.

Non-Profits 90

Non-Profits Growth Contact Customers 90

SaaStr

SEPTEMBER 13, 2023

Is everything going to be focused on AI? That pond is stocked with new opportunities that will get fished out over time. The best opportunities will get taken. 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

APRIL 5, 2023

The first was Salesforce, to get our CRM going (today, we would likely have gone with HubSpot). I fell so in love with support automation, when I invested, I did a ton in support, from Talkdesk (first VC), to Front, to Gorgias (#1 e-commerce contact center) to MaestroQA and more. As a tough result, their market cap is $335m.

E-commerce 97

E-commerce Contact CRM Service 97

SaaStr

OCTOBER 18, 2023

Founder Josh James had one of the earliest $1B+ exits in SaaS when Adobe bought his first start-up, Omniture, for $1.8 Josh is Spending a Ton of Time on the Road With Customers to Get Back to Growth. This is how you do it, folks #2. So Domo is an interesting case study on SaaS entrepreneurship. Billion way back in 2008.

Contract 96

Contract Price Growth Launch 96

SaaStr

JULY 10, 2022

I originally wrote this post way, way back in the first year of SaaStr and have updated it every 2 years or so, because it’s an important thing to think about as a founder. More is better, but less is going to create issues. Let’s take a look at 3 B2B acquisitions from a few years back as an example. the amount raised.

Price 142

Price Up-sell Growth Start-ups 142