SaaStr

APRIL 20, 2025

Dear SaaStr: How Should I Actually Set the Sales Plan for the Year For My VP Sales? This is where you build your operational model: sales hiring, marketing spend, product investments, etc. If sales slow down or the market shifts, this is the plan that keeps the lights on. Try the C10, C60, and C90 framework.

Sales Hiring 162

Sales Hiring Sales Communication Revenue 162

SaaStr

MARCH 7, 2025

It begs the question: is the sales and revenue acceleration space back? It shows budget remains in the sales acceleration space where and when its earned. Gong in the early days of this wave was often hurt by consolidation, but today it seems to be benefitting as it itself has become a much broader platform and multi-product.

Engagement 219

Engagement Sales AI B2B 219

Sales Hacker

NOVEMBER 29, 2024

That’s why HG Insights created The Next Generation of Sales AI report — to calm the FOMO and help you bring AI to your GTM teams. It includes a breakdown of the Sales AI landscape, adoption of GenAI and Sales software across buyer groups. Plus, an analysis of the top 75 trending sales AI tools. You’re not alone.

Investment 113

Investment Technical Review Development Team Review Scale 113

SaaStr

MAY 4, 2025

Dear SaaStr: How will Ai Change Sales in The Next 12 Months? It’s already fundamentally remade the contact center and post-sales. And it’s just getting there in sales. This will take sales calls from 10% being great to 95% being great because the AI will always be prepared and accurate.

AI 157

AI Scale Sales SMB 157

SaaStr

APRIL 1, 2023

We hired folks that really never understood the product in sales, or that never really finished any projects in marketing. The same things happened in VC and investing. I did some of this myself, both on people and investments. Better to do with fewer people, fewer investments, fewer initiatives. We learned.

Sales Hiring 312

Sales Hiring Investment Leadership Startup 312

SaaStr

MAY 5, 2025

I know your sales team probably hates pilots, because in a sense, it means they have to sell the deal twice. Having an “opt out” clause after a pilot ends helps, but still, it’s a double sale. Faster Decision-Making : A successful pilot can accelerate the sales cycle. Risk reduction is key.

Enterprise 242

Enterprise Leadership Investment Metrics 242

SaaStr

SEPTEMBER 20, 2024

Dear SaaStr: Do angel investors or seed venture capitalists normally ask for detailed budgets including cash flow analysis before investing, even though most of the numbers will be pure speculation? Do they really understand how marketing works, and/or sales works? Of course any early-stage (or even late-stage) model is “wrong”.

Investment 303

Investment Sales Hiring Business Model Sales 303

SaaStr

NOVEMBER 27, 2024

For restaurants, it’s the back end, front end, point of sale, payroll, ERP, and workforce management. Mangomint has one onboarding manager for every two sales reps, but with no contracts and a 30-day free trial, onboarding starts during the trial. Most sales reps hate it. There will likely be multiple Toasts for SMBs.

SaaS Payments 257

SaaS Payments Payments Payment Solutions Payment Services 257

SaaStr

NOVEMBER 13, 2024

But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. Outside of a pre-IPO phase, Klaviyo has been cash-flow positive or close for most of its history. Today, it’s steadily driving its margins up, now up to 14% non-GAAP operating margins.

Scale 301

Scale SMB Scaling Enterprise 301

SaaStr

DECEMBER 23, 2024

Share everything anyone would want to know to invest in you. Selling stock is sales. But unless you are raising from folks that truly invest pre-revenue, investors are going to want to see 3 strong months of growth in a row. Almost all early stage VCs read and invest in cold email. Share the deck when asked.

Venture Capital 274

Venture Capital Investment AI Metrics 274

SaaStr

MARCH 15, 2025

It’s live on SaaStr.com itself and you can also access it here and talk to AI Jason about any of 1000s and 1000s of B2B, sales, SaaS, VC, etc. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days.

Sales Hiring 258

Sales Hiring AI Scale Compensation 258

Clouded Judgement

NOVEMBER 18, 2024

The purpose of the detailed information is to help investors (both institutional and retail) make informed investment decisions. The document contains a plethora of information on the company including a general overview, up to date financials, risk factors to the business, cap table highlights and much more.

Benchmarks 299

Benchmarks Payments Payment Services SaaS Payments 299

SaaStr

NOVEMBER 20, 2024

Other Learnings in the GTM Journey GitHub has had to adjust to new sales stages and new buyer personas. There was a proliferation of conversations centered around legal, privacy, and models that took much longer in these sales stages than ever experienced. Another big investment during rapid growth is digital moments.

Scale 261

Scale AI Scaling Marketing 261

SaaStr

JULY 5, 2022

By moving from Freemium to “Contact Me” only (albeit with transparent pricing), sales went way, way up. So many sales leaders get frustrated with Free editions, very low-cost editions … and the Long Tail in general. The Long Tail : Distracts sales , with leads that never closes. Super power, over many years.

Scale 326

Scale Sales Engineering Acquisition 326

SaaStr

APRIL 28, 2025

The Journey: From WiFi to IoT Fleet Management Sekar’s journey began unexpectedly when he joined Meraki (founded by MIT researchers Sanjit Biswas and John Bicket) to help them figure out marketing and sales “from first principles.” This cross-pollination effect accelerated product development in unexpected ways.

Scale 260

Scale Transportation Scaling SMB 260

SaaStr

SEPTEMBER 9, 2022

Back in the day, premium comp for some software sales execs made simple and easy sense. Traditional software had 90% gross margins, and the classic enterprise sales reps, the best ones, could close a million or more dollars a year. Sales reps in low NRR and high churn environments got paid almost the same as enterprise reps.

Scale 345

Scale Venture Capital Sales Hiring Sales 345

SaaStr

OCTOBER 13, 2024

I try to work with (and invest in) CEOs that are better than me. Or didn’t want to do sales. She should hire leaders for Sales, Marketing, Engineering, Product and Customer Success, or at least most of them. Dear SaaStr: Why did Jason M. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups?

Sales Hiring 260

Sales Hiring CTO Hire Scale Startup 260

SaaStr

JUNE 5, 2024

So several times now I’ve seen the #1 sales rep that was just crushing it for quarter after quarter … then a few years down the road … later become one of the lowest performers. A new VP of Sales? The post When The #1 Sales Rep Stumbles appeared first on SaaStr. From #1 to the bottom of the leaderboard. Not usually.

Scale 299

Scale Sales Startup Investment 299

SaaStr

MARCH 16, 2025

Marketing leaders face crushing expectations from all sides: Management wants leads Sales needs collateral Product needs launches The team wants career growth The instinct is to spread your resources across everything: blogging, analyst relations, PR, events, SEO, paid search, content marketing, and more. The problem?

Scale 242

Scale Sales Hiring Scaling Marketing 242

SaaStr

NOVEMBER 28, 2024

I try to look at two things in Vertical SaaS startups, at least when investing : Will everyone in the vertical / industry use it? The good news is, you can support these price points effectively with a very efficient inbound sales team, and/or a mix of self-serve and sales-led. Or at least $10,000 at a minimum?

Payment Solutions 261

Payment Solutions Inbound Sales Team Marketing Scale 261

SaaStr

OCTOBER 31, 2023

— Jenny Fielding (@jefielding) October 17, 2023 So one of the parts I like least about investing is the follow-up. A few times a year, I’ll meet founders and a company I believe in so muc h, I’ll clearly offer to invest at the first meeting. Sales execs. And raising VC capital is sales.

Investment 273

Investment Metrics Sales 273

SaaStr

MAY 1, 2023

Dear SaaStr: Is It Acceptable for VCs to “Ghost” Founders who have invested so much time and effort with them? Working with VCs is sales. Ghosting is frustrating and not cool in any sales process. Most deals don’t close in sales. You’re lucky as a sales rep to close 20% of the warm leads you get.

Investment 273

Investment Venture Capital Startup Engagement 273

SaaStr

JANUARY 25, 2025

Thats just how investing work. And it can turn a $53m sales into one that makes a few millionaires. Marketing automation vendor Act-On acquired for $53 million [link] — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) January 25, 2025 So a lot of folks somehow think venture capital is bad, that it throws founders under the bus.

Venture Capital 239

Venture Capital Investment Retention Pricing 239

SaaStr

APRIL 5, 2025

Here are the five channels that worked for Rupa: Search Engine Optimization (SEO) Social Proof and Trust Building Educational Partnerships and Rupa University Conferences and Event Sponsorships Outbound Sales and Data Quality Lets dive into each. Rupas sales team sent highly specific emails, doubling their ROI.

Scale 229

Scale AI Search Sales Hiring Acquisition 229

SaaStr

JULY 8, 2024

How much more could you accomplish with your sales organization? Justworks CRO, Robert Lopez, and Director of Sales, Valeria Avila, show you how to create longevity in your sales organization and why it matters. Theme 2: Invest in Team Development Team development can happen in two powerful ways.

Sales Hiring 287

Sales Hiring Scale Sales Education 287

Sales Hacker

FEBRUARY 3, 2025

More operators behind fast-growing SaaS companies are turning to angel investing - not just as a way to diversify but to actively support the companies they believe in.This is core to GTMfunds thesis: providing investment access and opportunity to operators.

Investment 78

Investment Strategy SaaS Sales 78

SaaStr

MAY 25, 2024

Cloudinary VP of Developer Experience Sanjay Sarathy shares his journey to more than $100M and the lessons he learned along the way for building a PLG motion and an Enterprise sales motion. They didn’t initially envision being a large Enterprise sales organization. Let’s first start with how Cloudinary came to be. The takeaway?

Scale 312

Scale Sales Hiring SaaS Payments Development 312

SaaStr

DECEMBER 12, 2024

So theres a theme Ive been working on with all the SMB-focused founders I work with and have invested in: # 1. They improve onboarding, and integrations, and training, and sales comp plans, and more, and that all helps and is crucial. The Goal for SMB SaaS is 100%+ NRR. Easy in enterprise, hard in true SMB. #

Churn 273

Churn SMB Payments Payment Solutions 273

SaaStr

MARCH 18, 2025

The result was a 5x increase over initial projections – growing from an $8M revenue target to $40M actual results – driven by a belief that market demand justified the investment. This approach required immense trust from the CEO to invest millions ahead of proven results.

Scale 185

Scale Sales Hiring Scaling Headcount 185

SaaStr

MARCH 20, 2023

Dear SaaStr: How Do You Become Successful at Enterprise Sales? If you haven’t done enterprise sales before, the biggest thing to understand: you can do it. But for enterprise sales, you’re going to have to get your arse out of your home office and go close some real live human beings: Listen — often in person.

Scale 307

Scale Sales Hiring Enterprise Sales 307

SaaStr

OCTOBER 28, 2024

share of the profits on the investments) for a long time, if ever — and your job likely will be to hunt. Third, you are going to have to find some way to get really good at sales. It takes a long, long time for early-stage funds to make “distributions” of their profits from investments. And that is hard. Fourth, Why You?

Sales Hiring 301

Sales Hiring Compensation Branding Investment 301

SaaStr

MAY 9, 2023

One of the most essential things SaaS founders need to get right is their sales strategy. From day one, it’s critical to drive results to impress your investors, acquire customers, and set your sales team up for success. As a founder, it’s vital for you to be a big part of sales, especially in the early stages of your company.

Sales 307

Sales B2B Consulting Investment 307