SaaStr

JANUARY 22, 2024

Never have a tough conversation over email No matter how tempting it may be — Jason ✨Be Kind✨ Lemkin  ?? jasonlk) January 3, 2024 So perhaps the best management advice you’ll hear again and again is this: #1. Never Have a Tough Conversation Over Email Yes, you probably know this. And yet, most of us only half listen.

Conversion 101

Conversion Cross-sell Up-sell Start-ups 101

Partners in Excellence

MAY 1, 2024

Andy Paul and I were having what I’ve labeled “The Old Fart Conversations About Selling.” ” Neither of us feel we are out of touch with modern selling, the challenges both buyers and sellers face. But every once in a while we get on a call to discuss “What’s happening in selling?”

Technology 115

Technology Technology CRM Pipeline 115

SaaStr

NOVEMBER 28, 2023

So no question many folks, especially selling sales and marketing tools, are having a pretty tough time of it. Leaders we admire and look up to from Zoominfo to Zoom to Box have had tough years on the stock market, no doubt. Almost Everyone’s Gotten Radically More Efficient in SaaS The post Times Are Tough for Some.

Price 97

Price Up-sell Growth Sell 97

SaaStr

MAY 10, 2024

So HubSpot had a great quarter, despite there being many challenges in the sales and marketing segments overall in the past 18 months: $2.5B Even as many selling software to tech have struggled, HubSpot has maintained top-tier growth. It’s still tough out there. So maybe it’s a sign. Still, even now.

B2C 86

B2C B2B Growth Price 86

SaaStr

APRIL 7, 2024

So just a little while back, Lenny Rachintsky had me on his hyper-popular podcast to talk about scaling sales, from the perspective of a founder who hasn’t really done sales. A great summary of so many of our learnings. Try to close the first 10-20 customers yourself beyond you hire 1-2 reps, so you know how to do it.

Sales 98

Sales Quota Closing Up-sell 98

SaaStr

FEBRUARY 21, 2024

So an interesting case study is Blackline. 2023 Was Tough, But Predicting a Return to 20%+ Growth I love the boldness here with Therese back as CEO. Then 2023 was tough, and Therese came back. One of the most powerful things in SaaS is having a visionary founder-CEO. Nothing against an outside CEO. Jobs come and go. Folks stay.

Growth 82

Growth Up-sell Sell Customers 82

Cerebral Selling

MARCH 4, 2024

The results: 114% increase in sales 233% increase in cross-selling 300% increase in business referrals 71% increase in customer satisfaction 36% increase in productivity 77% decrease in turnover 90% decrease in absenteeism. So what magical sales leadership skills unlock this remarkable upside? helped me through a tough time in my life.”

Cross-sell 130

Cross-sell Sales Referrals Launch 130

Partners in Excellence

JUNE 5, 2023

“Tough times demand tougher selling!” ” That seems to be a mantra many people discuss about selling in a difficult economy. And tougher selling is, sometimes, interpreted of higher activity levels, more outreaches, higher volumes, more and more frequent touches. If you can’t answer these questions.

Sell 94

Sell Government Pitch Clients 94

Partners in Excellence

DECEMBER 4, 2023

If you don’t know/follow Brian, you should, he’s one of the best thinkers/practitioners I’ve met in selling. So why change? As a result, the selling becomes product focused, “ours checks more boxes.” There is no reason to do anything except product focused selling.

Customers 115

Customers Pitch Meeting Sell 115

Heinz Marketing

MAY 13, 2023

We’ll miss a ton of great stuff, so if you found something you think is worth sharing please add it to the comments below. So, what research should you do? How to encourage SDR resilience in tough selling conditions by Anthony Mennie When selling conditions get tough, it’s challenging to motivate SDRs and keep productivity up.

B2B 102

B2B Sales Drivers/motivators Up-sell 102

SaaStr

MAY 25, 2023

If so, say No If not? Probably just say Yes pic.twitter.com/K483lKnyzd — Jason ✨Be Kind✨ Lemkin  (@jasonlk) April 21, 2021 So I wrote a version of this post years ago, about when to think about selling your startup, if you do get an attractive offer. It’s OK so long as you are hotter. Not sure what to do?

Sell 144

Sell Price Up-sell Start-ups 144

Partners in Excellence

AUGUST 21, 2023

Appreciation is one of those “soft” topics that tough minded business people, focused on the numbers and growth, don’t tend to appreciate. Showing genuine appreciation, is so simple, yet helps us achieve so much! Appreciation has rich dimensions. It is critical in driving employee engagement.

Trust 99

Trust Pipeline Growth Customers 99

SaaStr

APRIL 4, 2024

So how you can do your own diligence as the first senior sales exec going in? Is it the right selling environment for you? More here: One Tough (But Rewarding) Job: Being the First Sales Rep at a SaaS Startup (first one image from here ) The post I’m Thinking of Joining an Early Stage Startup as the First Sales Exec.

Sales 84

Sales Up-sell Sell Customers 84

SaaStr

FEBRUARY 6, 2024

It would have taken so long, with so much risk, to ever get to $1b in value, it’s tough to argue with. That sounds great, but we had to sell 60%+ in the seed round to get it done (tougher times), and we were likely 5 years away from market, with a ton of regulatory and other risk. The VCs were too greedy here.

Sell 76

Sell Up-sell Price Start-ups 76

Partners in Excellence

APRIL 20, 2023

So the things we needed to do in good times, we are now challenged to do more of those things with fewer resources in bad times. All the time, but particularly in tough times, it’s critical to go deeper with our customers. Without a doubt, selling in tough times is much more difficult.

Prospecting 87

Prospecting Meeting Closing Sell 87

SaaStr

MARCH 21, 2023

But a lot of startups that sell nice-to-have products, especially in sales, are deeply struggling right now. So pseudo-SaaS products and other products with lower gross margins are commanding much lower valuations. So pseudo-SaaS products and other products with lower gross margins are commanding much lower valuations.

Up-sell 116

Up-sell Product Sell Sales 116

SaaStr

FEBRUARY 19, 2024

So the other day I did a 20VC with Harry Stebbings, and one of the topics that came up was the Hopin founder ‘s $100m+ secondary that the CEO took out of the company. It would have pushed me not to sell. While the company is still around, the Hopin product was subsequently sold for pennies on the dollar to RingCentra l.

Trust 92

Trust Up-sell Closing Sell 92

Cerebral Selling

APRIL 6, 2021

365 days after the release of Sell The Way You Buy , here are some of my key sales lessons learned from a year of pandemic selling. Value is a subjective feeling that can vary wildly in different selling situations. Value is a subjective feeling that can vary wildly in different selling situations.

Sell 136

Sell Objection handling Hospitality Pitch 136

Partners in Excellence

MARCH 5, 2024

Preface : Gus Maikish is one of the first people I met when I started my selling career. I was blown away when Gus opened a very difficult conversation in a direct and tough minded way. It’s not an esoteric book on theories, it’s a pragmatic focus on the job and how to sell both to the customer and within your own company.

Sell 77

Sell Contract Retail Account management 77

Force Management

MARCH 2, 2022

Give your salespeople the knowledge, skills and tools to differentiate their sales approach from tough competition. Regardless, good selling is good selling. Enable your salespeople to differentiate not just what they sell but also how they sell to help them win more opportunities this year.

Sell 112

Sell Conversion Sales 112

SaaStr

NOVEMBER 2, 2023

So we’ve spent a ton of time over the years on SaaS talking about hiring a great VP of Sales. 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. Or puts in the effort to do so. Don’t make this hire. Ask who those 2-3 are.

Process 92

Process Sales Up-sell Quota 92

Veloxy

JUNE 23, 2021

For most companies, selling virtually has become the new norm. And although some have taken to virtual selling like a fish to water, more and more businesses are struggling to adjust. So, how can we work on fixing a lot of these virtual selling challenges? 10 Steps to Building a Virtual Selling Team. Stop waiting.

Sell 317

Sell Education CRM Up-sell 317

Partners in Excellence

MAY 8, 2024

Desperately, we try to find someone to talk to, something interesting to talk about, but…… It seems so much of “modern” selling looks like this. It’s so much simpler that way. They’ve done all the hard work had the tough/interesting conversations.

Price 68

Price Up-sell Conversion Presentation 68

Cerebral Selling

MARCH 18, 2024

So if you find yourself in that position, it might seem natural and even efficient to quickly dispense answers and advice from your vast stock of experience when reps bring you sales or deal-related questions. Give them room to navigate tough situations with your guidance, not by assuming total control. Should we agree?” “I

Objectives and Key Results 164

Objectives and Key Results Legal Negotiate Trust 164

SaaStr

OCTOBER 16, 2023

So in the end, I did my very best, but … I didn’t stay all that long for zero incremental dollars. Having to use their sales team for future expansion, that also sells 4 other products? That can be tough. Especially if the sale is around 5 years or so, that’s when everyone gets tired. And it can’t be 100% punitive.

Consult 95

Consult Sell Product Sales 95

Hubspot

AUGUST 14, 2023

For instance, let‘s say a salesperson is selling a product that isn’t backed by 24/7 support — and once upon a time, that factor held up a deal or two. So when they're presenting to a prospect, they hastily speed through the support slide in their presentation deck. In turn, those unfortunate experiences have the rep rattled.

Closing 88

Closing Hospitality Negotiate Price 88

Partners in Excellence

JULY 18, 2023

But we make things so complicated, we make it much harder than it should be. When things get tough, for instance the economy, or even you may be behind in your numbers, narrow your focus even more. Our natural reaction when times get tough is to broaden our outreach, to find more possible prospects. Tilt the odds in your favor.

Pipeline 80

Pipeline Price Strategize Up-sell 80

SaaStr

MARCH 11, 2024

So you’re hiring your first few sales reps in the early days? So you need a very certain type of sales rep. They Can’t Sell You This Pen I don’t know if these days, a sales rep has to come to the first interview being able to do a strong sales demo of your sales product. Can you still “sell”?

Sales 92

Sales Up-sell Promote Meeting 92

Veloxy

AUGUST 28, 2023

So, how does a savvy salesman gain a competitive advantage over the rest? Everyone tends to follow the same routine every day – so it makes total sense that your general thought pattern is the same from morning to night. Call it magic, call it cheating. Covert hypnosis is a bit stealthier and backed by science. What is Covert Hypnosis?

Technique 130

Technique Sales Prospecting Up-sell 130

Partners in Excellence

APRIL 8, 2024

Yet there are so many challenges and barriers. Our fixation on mechanizing everything in selling, minimizing the human connection, and our failure to connect with customers on their problems/challenges. Kiss those selling jobs good-bye! Every quarter there is the inevitable rush to close deals, to hit our numbers.

Quota 117

Quota Trust Pitch Up-sell 117

SaaStr

MARCH 30, 2023

This is a tough and very specific job. Usually, being the first start-up salesperson is a rewarding, but very tough job: Your boss has never probably managed a salesperson before. So this is a tough job With not a truly typical day. Most sales folks can’t do. Everything.

Quota 87

Quota Start-ups Up-sell Closing 87

Veloxy

APRIL 28, 2021

A sales rep is only as good as the time they spend selling. Let Sales AI take care of all non-selling activities so your reps can focus on revenue generation. Artificial intelligence in sales can increase selling hours by not only automating tasks, but also improving daily productivity and analyzing habits.

Cross-sell 289

Cross-sell Sales Quota Pitch 289

Iannarino

JULY 10, 2021

But the advice here is designed to be helpful in many client conversations, not just the tough ones. But the advice here is designed to be helpful in many client conversations, not just the tough ones. The Gist: Preparation can improve your ability to deal with client conversations, especially difficult ones. The key is preparation.

Clients 284

Clients Conversion Up-sell Start-ups 284

SaaStr

JULY 16, 2023

And today — it seems so far from easy. We’ve Never Seen That Before Today, an acquisition can seem so much easier. A chance to sell late stage and make tens or even hundreds of millions is not just a once-in-a-lifetime opportunity … but also a chance to get a mental break. And yet … if you do sell … that’s it.

Price 88

Price Sell Closing 88

SaaStr

AUGUST 24, 2022

So we took a look at Toast just after it IPO’d. 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. 68,000 total locations, so about $12,000 per year per location (or $1k per month).

Territory 115

Territory Referrals Growth Price 115

Partners in Excellence

FEBRUARY 8, 2024

The net of his broetry said, “Average leadership tenures are 17 months… To protect yourself get a side gig… Do consulting on the outside… Maybe over time move into consulting and fractional roles… ” There is so much flawed logic in this. Sadly, too much of this is from smart people who should know better.

Consult 124

Consult Clients Follow-up Up-sell 124

SaaStr

JULY 7, 2021

then really there’s only so much investors can really do. then really there’s only so much investors can really do. So as long as you don’t sell too much of your company, really the meanest thing VCs can do is Not Support The Company. Second, it can be a real issue in M&A, when you sell the company.

Finance 141

Finance Legal Up-sell Gaming 141