SaaStr

JUNE 17, 2025

A bit more on that here : How to Cope With Long Sales Cycles But there are plenty of things that help : Hire a VP of Sales with Enterprise Experience : A great VP of Sales who’s closed deals at your price point can shave months off your sales cycle. They know how to navigate pilots, engage stakeholders early, and avoid late-stage objections.

Sales Hiring 175

Sales Hiring Enterprise Sales SMB 175

SaaStr

JANUARY 23, 2025

You need to: Engage with procurement early – don’t treat them as a rubber stamp Build relationships with 20+ key accounts in year one Get executive sponsorship on both sides Never negotiate price with the business buyer Document clear ROI and business cases Remember: The actual buyer is often not the end user.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

MAY 28, 2025

The company is successfully evolving from its SMB roots into a serious enterprise software contender. Their Customer Base Has Grown 22% CAGR Since 2019 Despite Higher Prices Monday.com has grown from 90K customers in FY-19 to 245K customers in FY-24, representing a 22% CAGR over five years. And a Few More Interesting Learnings: 6.

Scale 199

Scale SMB Acquisition Enterprise 199

Clouded Judgement

JUNE 17, 2025

This matters a lot more when stock prices are going down, and management teams often grant additional shares to make employees whole (thus increasing dilution even more) Net Revenue Retention High net revenue retention is the fourth aspect of a successful quarter, and one of my favorite metrics to evaluate in private SaaS companies.

Cloud 277

Cloud Software Benchmarks Retention 277

SaaStr

APRIL 14, 2025

Head of AI Dialpad: How to Build AI at Scale GTM/ B2B Speakers: CEO HubSpot Yamini Rangan: Going More Multiproduct, Going More AI, and Going More SMB and More Enterprise CEO Dropbox Drew Houston: DropBoxs Third Act: AI & Content Intelligence CEO Calendly, Tope Awotona Open AMA and AI in 2026 CEO Clio, Jack Newton: Reaccelerating Vertical SaaS to (..)

VP of Engineering 204

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 204

SaaStr

APRIL 28, 2025

If a prospect asks about integrations, pricing details, or implementation requirements that you’re unsure about, you’ll simply ask your AI, and it will provide the perfect answer in real-time. It can handle pricing questions, objections, and proposals without emotional baggage or commission pressure.

AI 244

AI Underperforming Technical Team Sales Technical Review 244

Stax

JUNE 18, 2025

The most common challenges associated with vertical SaaS are competing for adoption against popular legacy or traditional SaaS solutions, a smaller lead pool that may soon exhaust, and managing the expectations of consumer-like SMB customers. What is Vertical SaaS? Q: Why is Vertical SaaS considered a profitable business model?

Merchant Services 167

Merchant Services SaaS Payments Payment Services Payments 167

SaaStr

JULY 23, 2025

Horizon 1: Individual Creators & SMB & Internal Apps (2025-2027) TAM: $2-12B This represents the current market: (1) individuals and small teams who need functional software, but lack technical resources or budget for custom development, (2) internal tools for more sophisticated tech teams, and (3) prototyping and proof-of-concept.

Software Review 194

Software Review Technical Review Development Team Review Systems Review 194

SaaStr

APRIL 12, 2025

For example: High-Intent Actions : Visiting your pricing page, requesting a demo, or engaging with a case study. For example: At Adobe Sign / EchoSign, we learned that SMB leads who hadnt used our product at least 3 times were far less likely to convert. Dont Convert Too Early Converting leads too early is a common mistake.

Systems Review 125

Systems Review SMB Engagement Sales 125

Sales Hacker

DECEMBER 17, 2024

Scott Barker: [26:53] Did you go about shifting that so how were what were some of the strategies you used to shift um how the market was perceiving you. Guy Yalif: [30:18] Your point, the field enablement part of marketing was a huge amount of work and fortunately uh.

Scale 102

Scale Engineering Acquisition Scaling 102

How To Buy Saas

FEBRUARY 25, 2025

In this in-depth comparison, well explore Salesforce vs. HubSpot across features, ease of use, pricing, use cases, and more so you can determine which CRM is the right fit for your organization. Rapid SMB adoption with 200K+ customers. Startups, SMBs, and mid-market; teams wanting all-in-one marketing + sales.

Scale 52

Scale Underperforming Technical Team Technical Review Marketplace as a Service 52

How To Buy Saas

MAY 26, 2025

In this comprehensive Skynova review , we break down its features, pricing, pros, cons, and how it stacks up against popular Skynova alternatives like QuickBooks, FreshBooks, and Wave. Skynova is an easy-to-use online invoicing tool with budget-friendly pricing, but its feature set is full of compromises.

Software Review 40

Software Review Systems Review Technical Review Payment Solutions 40

How To Buy Saas

MAY 21, 2025

Whether youre a startup , an SMB , or a global enterprise , the right ATS can streamline your recruitment process, save time, and help attract top talent in a competitive market. Breezy HR Best Free ATS for Small Businesses Pricing: Key Features: Ideal Use Case: 2. What ATS is best for small businesses or startups?

Systems Review 52

Systems Review Sales Recruiting Sales Hiring Technical Review 52

SaaStr

FEBRUARY 3, 2025

The Enterprise Pricing Journey Is All About Unbundling Stripe learned this the hard way. pricing was brilliant for SMBs but completely wrong for enterprise. You have to go all in.” Their famous 2.9% + $0.30 But if you get it right, the rewards are enormous.

Scale 272

Scale SMB Enterprise Enterprise readiness 272

SaaStr

OCTOBER 16, 2024

Everyone is going to have a pricing page, check the box, function app, and feature parity on everything that is AI and B2B, everyone. In the SMB space, the biggest problem is onboarding for complex products. They just crossed a billion in ARR, growing 34% with 110% NRR from SMBs and 22% free cash flow. Go more Enterprise or SMB.

Sales Hiring 317

Sales Hiring Scale AI SaaS 317

Chart Mogul

DECEMBER 12, 2024

2024 was a big year for SaaS with AI in the spotlight and new pricing models shaking things up. Some predictions were spot onAI-powered co-pilots, pricing experimentation, consolidation and M&A activity all surged. What will 2025 bring? This time last year, 24 SaaS experts predicted big things for 2024.

Fractional VPE 40

Fractional VPE Software Review SaaS Part-Time VPE 40

Stax

APRIL 3, 2025

Transaction fees and pricing models All payment service providers charge a fee for their services. And different providers adopt different pricing models, so you want to find a provider that matches your budget. Also, some providers lock premium features in high-end pricing tiers. Qualified payments have the lowest rates.

Payment Methods 88

Payment Methods Merchant Services Payment Solutions Payment Services 88

SaaStr

FEBRUARY 5, 2025

Pricing and Model Management The company charges customers based on success, only charging for full automation when a ticket is closed and resolved. The post Lessons Learned Rolling out AI Agents to 16,000+ SMB brands with Gorgias’ CTO appeared first on SaaStr.

New CTO 167

New CTO CTO Artificial Intelligence SMB 167

Sales Hacker

JUNE 17, 2025

And again, even in SMB, because I don’t only work with big enterprise organizations and I’m kind of stage agnostic, I [00:22:00] work with, you know, companies, hundreds of millions of revenue. I don’t think Prices Law works anymore. And in the lean ai, my hypothesis prices law doesn’t work.

AI 88

AI Technical Advisors Underperforming Technical Team Sales Hiring 88

User Pilot

FEBRUARY 12, 2025

Heres how you can apply our process to find out why youre experiencing more churn: Redefine the problem: Theres been a 20% increase in customer churn rate over the past three months, primarily among SMB clients. It could also be due to a price increase that was announced three months ago.

Technical Review 59

Technical Review Software Review Churn SaaS 59

SaaStr

FEBRUARY 13, 2025

Here, we see threats when customer attempt to cancel, big price increases every year, and renewal managers trying to force customers to buy extra seats they don’t need. Not just for consumer and SMB. So there are two massively different vibes in B2B and Cloud and SaaS today: Folks fighting to keep slowing growth going.

AI 209

AI ChatGPT SMB Enterprise 209

Sales Hacker

JANUARY 7, 2025

So you need to have that because those, especially if you think about SMB, They don’t have, I would say, technical people inside their organization. And I’m a big believer in the SMB space. It’s in the SMB. It’s helping the SMB, the emerging business, disrupt and change a bit the landscape in some areas.

Outsourcing Services 117

Outsourcing Services Scale Outsourced Development AWS 117

Blulogix

JUNE 13, 2025

The Cost of Getting It Wrong Too many enterprises are running billing on SMB-era infrastructure—or worse, fragmented systems patched together by IT. Does it support usage and hybrid pricing out of the box? Ask questions like: Can it handle multi-entity operations with shared and unique catalogs?

Payment Features 59

Payment Features Enterprise Traceability Scale 59

Sales Hacker

APRIL 1, 2025

The exact playbook to move from SMB to enterpriseincluding partner enablement, segmentation, and incentive design. 85% of your customers being SMB and mid-market to at the end of that six years, it was 75%, uh, enterprise. One last thing we also did was we started playing with pricing and the incentives that we did with partners.

Scale 63

Scale VP of Engineering Outsourcing Services Enterprise 63

Sales Hacker

FEBRUARY 25, 2025

Obviously, SMB, smaller companies, there’s risk when the market’s the way it is. Therefore refine the product strategy, the roadmap, eventually pricing and packaging, and all of this, by the time we got to the point of, you know, due diligence, it was solid, we weren’t operating just off of.

Sales Hiring 84

Sales Hiring Marketing Technical Review Sales Recruiting 84

SaaStr

APRIL 1, 2025

This created almost opposite playbooks for their SMB vs. enterprise motions, complicating their enablement strategy. DataBricks: Pricing Power Trumps Efficiency CRO Ron Gabrisko’s surprising revelation during his time taking DataBricks from $1B to $3B was that focusing on pricing power created more leverage than operational efficiency.

Scale 208

Scale Sales Hiring Underperforming Technical Team Headcount 208

Sales Hacker

JULY 8, 2025

And then finally tell me the price, whereas a lot of other companies are like who can we afford or what’s in the realm of that? So if he said, for example, I want to build a billion dollar marketing cloud, it was almost like who’s the leader, who do we need to acquire? And just they think at a different level.

Sales Recruiting 82

Sales Recruiting Sales Hiring AI Search Scale 82

SaaStr

JULY 10, 2025

But Toast went a more “SMB” route focusing on smaller restaurants and chains. larger revenue base by 2025. Sometimes the bigger market wins, even with lower initial margins. When are smaller customers “better”? Olo was just acquired for $2B by Thoma Bravo after 20 years — a big success. That’s lead to a $25B market cap today. 10x larger.

Technical Review 175

Technical Review Payments Scale Payment Solutions 175

Sales Hacker

DECEMBER 31, 2024

And it may even be different in different markets, geographic markets, like SMB, mid market, enterprise. Like, you know, is it, is it some other, some other modernization motion that we need to do? Is it a comp, like what is it? Um, and then build your playbook for that. Um, I think a lot of that’s going to change.

Sales Hiring 106

Sales Hiring B2B Scale Sales Recruiting 106

The Moz Blog

JUNE 10, 2025

MozCon Save on Early Bird tickets and join us in London or New York City Moz API Unlock flexible pricing & new endpoints Find your plan Blog Why Moz Digital Marketers Simplify SEO tasks to save time and grow your traffic. Moz Academy Upskill and get certified with on-demand courses & certifications. a Ziff Davis company.

Branding 86

Branding AI Search Scale AI 86

SaaStr

APRIL 14, 2025

Closing high-ticket enterprise deals is a different beast compared to SMB or mid-market sales. Most SMB sales reps and even most founders aren’t very good at this. Simplify your pricing, contracts, and approval processes. Position your product as a solution, not just a tool, and price it accordingly. Force yourself.

Enterprise 162

Enterprise SMB Finance Pricing 162

SaaStr

MARCH 30, 2025

Co-founders Dharmesh Shah (CTO) and Brian Halligan (Chairperson) shared at SaaStr Annual the unfiltered truth on building an SMB powerhouse, pivoting to product-led growth, and why the “M” segment is SaaS gold. The SMB market offered a sweet spot between enterprise complexity and consumer scale. The result?

Scale 194

Scale SMB Sales Hiring Scaling 194

Sales Hacker

JUNE 13, 2025

The real bottleneck is Series A Raising a priced seed round is no longer the milestone it once was. More conviction, fewer bets. This is the paradox: it’s harder than ever to raise, but for the right company capital is still abundant. The real crucible is graduating to Series A.

AI Search 94

AI Search Sales Hiring Sales Recruiting Scale 94

Sales Hacker

MARCH 25, 2025

Why traditional SaaS pricing models (like per-seat) dont work in the agent era. 25:15 Why legacy SaaS pricing models dont work for agentsand what comes next. I guess hindsight is 2020, but looking at apps and mobile, the pricing to me, at least just always kind of made sense. What are your thoughts on pricing?

AI Search 69

AI Search AI Scale Software 69

SaaStr

FEBRUARY 7, 2021

Let’s break down for example what SMB sales at low price points typically is, and indeed needs to be, to scale: SMB SaaS companies are overloaded with “leads” They often have so many that they cannot follow up with all of them. SMB sales reps have to be hyper-efficient. You sort of have to.

SMB 332

SMB Sales Hiring Scale Enterprise 332

SaaStr

APRIL 28, 2021

As Shopify crossed $4B ARR, it actually got a bit more SMB. It’s just its SMB customers grew even faster — at $4B in ARR! So SMB revenue at Shopify grew to 74% at $4B, up from 72%. So SMB revenue at Shopify grew to 74% at $4B, up from 72%. And as Zoom crosssed $4B in ARR, it actually got a lot more SMB.

SMB 322

SMB Cloud Enterprise Scaling 322

SaaStr

SEPTEMBER 19, 2023

based SMB sales positions. Almost every SMB SaaS company I work with has moved most of its sales team outside the U.S. Almost every SMB SaaS company I work with has moved most of its sales team outside the U.S. These all sprung up as more cost-effective centers of excellence for SMB and even some mid-market sales reps.

SMB 313

SMB Scale Sales Hiring Sales 313