SaaStr

NOVEMBER 10, 2023

Dear SaaStr: What Were Your Toughest Times Before Breaking Out? My toughest times: COO pulling out after signed term sheet — VCs then pulled term sheet. But boy it was tough. Man that’s tough. That was tough. I tried 5 times, maybe 10. This of course was my fault — I hired the “wrong” COO.

Engineering 94

Engineering Closing Product Sell 94

SaaStr

JANUARY 22, 2024

Never have a tough conversation over email No matter how tempting it may be — Jason ✨Be Kind✨ Lemkin  ?? Never Have a Tough Conversation Over Email Yes, you probably know this. As tempting as it may be to avoid conflict, headaches, and hearing things you don’t want to hear — never have a tough “conversation” over email.

Conversion 100

Conversion Cross-sell Up-sell Start-ups 100

Partners in Excellence

APRIL 20, 2023

As we face tougher business and economic times, I see too many organizations implementing frenzied strategies of doing more–more prospecting, more outreaches, more activities, more deals. 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.

Prospecting 101

Prospecting Meeting Closing Sell 101

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. By the time they engage us, they have defined the problems, defined what they want to achieve, defined the solutions, and defined the products they are most interested in considering. So why change?

Customers 132

Customers Pitch Meeting Sell 132

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 127

Technology Technology CRM Pipeline 127

SaaStr

MARCH 5, 2024

Software all sort of all, rough-and-tough, costs the same to build and ship. Once you figure out how to really sell. But otherwise — it’s tough. Most first-time SaaS CEOs price too low and don’t drive ACVs up quickly enough because they don’t quite yet understand the context of the product.

Price 80

Price Product Up-sell Sell 80

Sales Hacker

NOVEMBER 21, 2023

Currently contemplating his next move, it will involve embarking on the journey of being a second-time founder. Tactics to encourage resilience and determination and how Mike maintained a strong mindset throughout the journey, even when times got tough. 9:46) Differentiating product-market-timing fit from product-market fit. (14:58)

GTM 99

GTM Sell Networking Go To Market 99

Cerebral Selling

MARCH 4, 2024

I’ve spent a lot of time studying the patterns and research around what makes great sales leaders. 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.

Cross-sell 130

Cross-sell Sales Referrals Launch 130

SaaStr

FEBRUARY 21, 2024

Sometimes, the time comes to hand the baton to someone else. But the times have changed, and folks are being asked to be even more efficient. 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. Nothing against an outside CEO.

Growth 80

Growth Up-sell Sell Customers 80

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. ” It’s investing the time to talk and work with those people. Appreciation has rich dimensions. It is critical in driving employee engagement.

Trust 114

Trust Pipeline Growth Customers 114

Heinz Marketing

MAY 13, 2023

How to Measure the Effectiveness of Your Sales Process by Tristen Taylor Keeping tabs on the effectiveness of your sales process is critical to helping you gauge the health of your sales organization and ultimately learning how to sell better. Great Sellers are Great Researchers.

B2B 102

B2B Sales Drivers/motivators Up-sell 102

SaaStr

MAY 25, 2023

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. They didn’t put a few bucks away last time. At other times, the price can be crappy.

Sell 144

Sell Price Up-sell Start-ups 144

SaaStr

APRIL 7, 2024

Hire your first salesperson when you have closed the first 10 customers and are spending more than 20% of your time on sales. Make sure your VP of Sales actually wants to sell, not just manage. It’s a tough job. And a lot of folks want to manage but not really sell themselves. And sales go down, not up. #2.

Sales 96

Sales Quota Closing Up-sell 96

SaaStr

SEPTEMBER 12, 2022

Hiring is tough, but if 12 months have gone by and you haven’t added 2 strong senior execs to the team, I get worried. Let everyone know ahead of time. The best CEOs telegraph these risks, without drama, but plainly and ahead of time. Slowdown in transparency, especially during tougher times. Too slow to hire VPs.

Gaming 108

Gaming Up-sell Sell Customers 108

SaaStr

FEBRUARY 6, 2024

I’ve been through it 3 times. The first time, the answer was price. It would have taken so long, with so much risk, to ever get to $1b in value, it’s tough to argue with. The second time, the answer was time & risk & dilution. The third time, well, most of the team was a bit tired after 5 challenging years.

Sell 77

Sell Up-sell Price Start-ups 77

SaaStr

AUGUST 9, 2023

Ok now that some time has gone by I can reflect a bit more thoughtfully here. We had a few tough hits with one strategic partner, and lost a few big deals. In some ways, it was a different time. Selling the company. This is a tough one, but in the end, selling when it was just getting good was a mistake.

Strategize 82

Strategize Gaming Sell Closing 82

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. Customers remember how you treat them during times of adversity. Your pitch needs to as well.

Sell 136

Sell Objection handling Hospitality Pitch 136

Partners in Excellence

JULY 18, 2023

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. Most of the time, sellers get involved in the very final stages of their buying process.

Pipeline 96

Pipeline Price Strategize Up-sell 96

SaaStr

MARCH 21, 2023

But a lot of startups that sell nice-to-have products, especially in sales, are deeply struggling right now. This can be tough to solve for. It’s tough to say this “aloud”, but the truth is, a lot of folks just didn’t work all that hard from mid-2020 to late 2022. Even in tougher times.

Up-sell 117

Up-sell Product Sell Sales 117

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 138

Consult Clients Follow-up Up-sell 138

SaaStr

MARCH 11, 2024

It’s an interesting time. If they send you a professional message ahead of time, that they need to push? 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 90

Sales Up-sell Promote Meeting 90

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. They never invest the time after they start, either. Hiring a VP of Sales That Actually Doesn’t Want to Sell Themselves Anymore This one has really become an issue in recent years, and the one hand I get it. Sales is hard.

Process 90

Process Sales Up-sell Quota 90

Hubspot

AUGUST 14, 2023

Value leaks undermine a buyer’s confidence in your solution, reducing your likelihood of closing — and even if you do win, you’ll have a harder time charging full price. 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.

Closing 87

Closing Hospitality Negotiate Price 87

SaaStr

OCTOBER 16, 2023

Most founders have hacked things, for a long time. Having to use their sales team for future expansion, that also sells 4 other products? That can be tough. Acquirers should recognize this and turn the CEOs into 50%-time consultants and “non-executive chairpeople” of their startups, until the help isn’t needed anymore.

Consult 94

Consult Sell Product Sales 94

Partners in Excellence

MARCH 5, 2024

Preface : Gus Maikish is one of the first people I met when I started my selling career. Since I was assigned to a different team, I didn’t spend much time with Gus, but remember one call that I tagged along. I was blown away when Gus opened a very difficult conversation in a direct and tough minded way.

Sell 77

Sell Contract Retail Account management 77

SaaStr

DECEMBER 27, 2022

Almost no products just sell themselves. As a first-time founder, a lot of folks won’t believe in you. Actually, investors that seem too nice are often just selling something. Folks you trust actually often give you some hard, tough advice. Folks you trust actually often give you some hard, tough advice.

Niche 133

Niche Trust Up-sell Start-ups 133

SaaStr

FEBRUARY 13, 2023

It’s really tough to go through. The root cause for mine, and most of the ones I’ve observed, is disalignment on goals and outcomes: Do you want to IPO, but your cofounder would be happy to sell for $2m? They both were second-time founders who already had “exits” and knew this time, they wanted to go big.

Cross-sell 84

Cross-sell Up-sell Sell Growth 84

Cerebral Selling

AUGUST 8, 2022

And in times of crisis, two things can happen: Fear and distraction give way to diminished revenue production, quota attainment, and rash decisions to leave for greener pastures (which we know don’t often exist). Here are five key strategies to lead your team through times of uncertainty. Assure them, this is normal.

Sales 199

Sales Contract Clients Quota 199

SaaStr

FEBRUARY 19, 2024

And in fact, the product was already in decline by the time the CEO took $100m+ out. If founders have been at it for 5+ years, and the business is truly at scale, and past the risk stage, then helping them sell some shares can be just the right thing to help them go long. It would have pushed me not to sell. But why ?

Trust 90

Trust Up-sell Closing Sell 90

Partners in Excellence

SEPTEMBER 19, 2023

We need so many opportunities, that we spend less time on each opportunity, and guess what? Since we need fewer opportunities, we can invest more time in those we qualify, further improving our win rates. Those people still have lots of crap inflicted on them, so it’s tough to standout. It is never about what we sell.

Pipeline 125

Pipeline Tradeshows High impact Technique 125

Martech

SEPTEMBER 30, 2022

This has led to some misunderstandings around the value of this role, and in marketing it’s a tough sell. Why is the Scrum Master role a tough sell? From those three anti-patterns alone, you can see why this role is a tough sell. Within these categories, there are several sub-pieces for implementation.

Launch 101

Launch Up-sell Meeting Clients 101

Partners in Excellence

APRIL 8, 2024

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! At the same time, too many have ignored the customer pleas for help! This combined with other data showing win rates at less than 20%.

Quota 128

Quota Trust Pitch Up-sell 128

Cerebral Selling

JANUARY 14, 2023

Year-end can be the most exciting time in sales. As an AE, you may be blowing through your number, signing deals, and having the time of your life. Been on Cloud Nine many times and have also struggled, falling short of where I needed to be. For a lot of teams, this year was tough and filled with uncertainty.

Quota 188

Quota Pipeline Drivers/motivators Negotiate 188

SaaStr

JULY 9, 2023

At least until somewhere between $10m and $30m ARR, depending on the category, competition, and timing. You’re always almost out of money, or at the edge of slowing growth, or just can’t find that critical VP you need, or build that feature in time. Maybe because there was never time to be down. But never down. Glorious, no?

Growth 83

Growth Sell 83

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. And, by the time they talk to us, there is very little we can do to shape their thinking. And by the time they get to this point, the customers are exhausted.

Price 68

Price Up-sell Conversion Presentation 68

SaaStr

AUGUST 21, 2020

Q: What are the signs that an entrepreneur will always be small time? And so, these also probably are start-ups you shouldn’t join, IF you want to be part of something that could be big: Talks a lot about selling the company for “say $20m-$30m”. Hiring is tough. It’s always tough. Always” is a bit extreme.

B2B 128

B2B Up-sell Start-ups Closing 128

SaaStr

JULY 7, 2021

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. But you’re in a tough spot for future fundraising if your prior round investors are actively or even passively, negatively un-supportive. Second, it can be a real issue in M&A, when you sell the company.

Finance 139

Finance Legal Up-sell Gaming 139