SaaStr

AUGUST 8, 2025

SDRs : Invest in 2–3 SDRs to generate pipeline for the AEs. Marketing : If marketing isn’t generating enough leads, you’ll need to invest here. Improve Onboarding : New reps should be fully ramped within one sales cycle. If you only have 2–3 reps now, hiring is a top priority. A good rule of thumb is 1 CSM per $2M ARR.

Scale

SaaStr

JUNE 24, 2025

It’s about fundamental organizational redesign —from pricing models (hybrid consumption/subscription) to team structures (forward-deployed engineers vs traditional CSMs) to investment priorities (94% AI spend increases among high-growth companies). The message is clear: The Age of AI isn’t coming—it’s here.

Scale

SaaStr

JULY 22, 2025

Invest in Sales Ops Early : Once you have 8-10 salespeople, you’ll need a Sales Ops/Enablement professional to manage training, onboarding, territories, and compensation plans, unless your VP Sales happens to be great at this. Be Ready to Invest : Building a world-class sales team isn’t cheap. By the time you’re at $1M-$1.5M

Sales Hiring

SaaStr

AUGUST 4, 2025

A shorter payback period means you’re recovering your investment faster, which is critical for scaling efficiently. This is under-tracked by most start-ups, leading to less investment in onboarding. Customer Acquisition Cost (CAC) Payback Period: This tells you how long it takes to recoup the cost of acquiring a customer.

Scale

SaaStr

MAY 10, 2025

Nail Onboarding, and Make It a Key KPI for CS Onboarding is where you win or lose customers. Use it to guide customers through onboarding and deliver value quickly. Invest in Relationships Customer success isnt just about metricsits about people. Dont wait until youre at $5M or later to invest in customer success.

Sales Hiring

Payrix

JANUARY 10, 2025

Ian Hillis welcomes David Blair, Senior Director of Product Management at Worldpay for Platforms, on PayFAQ: The Embedded Payments podcast to explore the critical roles of merchant underwriting and onboarding for software providers. Real-time feedback loops and data-driven optimizations are also transforming the onboarding experience.

Merchant Services

SaaStr

JULY 11, 2025

When AI can handle customer onboarding, support, and success functions that traditionally required human intervention, you can scale revenue without proportionally scaling teams. But here’s what’s really interesting: This efficiency advantage seems to fade as companies get larger.

Scale

SaaStr

MARCH 9, 2025

Previously, he led design teams at LinkedIn where he built recommendation products for product onboarding and developed AI chatbots. The 86% loyalty factor : Companies that provide strong onboarding and continuous educational experiences see 86% higher customer loyalty rates – making AI-powered personalization a critical retention tool.

AI

SaaStr

NOVEMBER 20, 2024

Once they brought it to market, they knew they needed better user admin features, onboarding capabilities, SSO integration, etc. Don’t underestimate the investments you need to make here to be compelling to your customers. Another big investment during rapid growth is digital moments.

Scale

SaaStr

JULY 31, 2025

Invest in Product Stickiness Your product needs to be indispensable. This could mean adding integrations, improving onboarding, or offering training to ensure customers are fully utilizing your product ‌. Get Better at Onboarding. Way too many SMB products see 10% of their new customers or more never onboard. Much Better.

Payments

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

SaaStr

JULY 23, 2025

Investment and Strategic Implications For VCs and Strategic Investors Category Investment Thesis : We’re witnessing the formation of a new software category with $100B+ TAM potential. Early-stage investments in platform infrastructure, specialized tools, and enterprise-focused solutions present significant upside.

Software Review

SaaStr

JUNE 13, 2025

You can hear our deep dive with Yamini Rangan, CEO of HubSpot, on how she is doing this at HubSpot here: A Better Approach: Democratize AI Investment Instead of concentrating AI expertise in one highly-paid executive, consider this alternative approach: Create AI experiment budgets for every team. Make AI fluency a core competency.

Sales Hiring

SaaStr

JULY 10, 2025

Plan to spend at least two weeks of intensive training, just like onboarding a new hire. The Bottom Line AI SDRs can work incredibly well, but only if you’re willing to invest the time to train them properly. What We’re Looking to Do Next We’re literally onboarding two more AI sales tools this week. The upside?

AI

SaaStr

JANUARY 23, 2025

Focus on: Building robust security and compliance (SOC 2, ISO 27001) Automating customer onboarding/offboarding Creating enterprise-grade support processes Developing procurement relationship expertise Having clear data handling procedures 5. Master Enterprise-Grade Operations The operational bar is much higher in enterprise.

Enterprise

SaaStr

JULY 2, 2025

Have them shadow customer success calls, onboarding sessions, and even product team meetings. Invest in Tools and Resources Don’t skimp on tools like Gong (for call recording and analysis), Apollo, or LinkedIn Sales Navigator. At seed stage, every dollar counts, but investing in the right tools can dramatically improve ramp time.

Sales

SaaStr

JULY 30, 2025

Stronger Commitment : Customers who pay annually are more likely to invest time in onboarding and using your product, which increases stickiness. But you need to address the root cause of churn too—whether it’s poor onboarding, lack of engagement, or product-market fit issues.

Churn

User Pilot

OCTOBER 31, 2024

These issues might range from low engagement with specific features to a high churn rate or poor user onboarding. To address this, you could meet with your team to agree on metrics related to onboarding, such as activation rate , time-to-value, and so on. This process may reveal gaps such as: Insufficient raw data. Outdated technology.

Strategy

SaaStr

JUNE 29, 2025

The Result : After pivoting from “payments only” to “payments + compliance,” they onboarded their first 100 clients and raised Series A. Onboarding became “very inefficient.” We test all of them with very light investment, very simple models. Three months later: Series B.

Payment Services

ChurnZero

APRIL 11, 2025

Your customer onboarding strategy is the foundation of your future retention and expansion revenue. The right onboarding strategy means more than just getting a customer using your product. But how do you know if your onboarding tactics really work? Is your onboarding process a framework or a free-for-all?

Onboarding

SaaStr

JULY 22, 2025

Invest in onboarding. If the average CMO lasts 1.8 years, maybe don’t structure their entire comp plan around 3-year performance metrics. Before You Start as a VP — Do a Real 60-Day Plan. And Make 100% Sure the CEO Agrees With It. Every month of ramp time is precious when the clock is already ticking.

Part-Time CTO

SaaStr

MAY 29, 2025

Do you invest in upskilling your middle performers, or do you focus resources on amplifying your stars? The result? More specialization in human roles, with AI handling the connective tissue between specialized functions. This creates a talent strategy challenge. The window for competitive advantage is narrowing fast.

Sales Hiring

SaaStr

APRIL 28, 2025

Product Will Need to Be More Self-Serve As AI handles more of the sales and onboarding process, there will be increased pressure to make products truly self-deployable. Companies will need to invest more in seamless onboarding, intuitive UX, and automated implementation to match the efficiency of their AI sales process.

AI

BetterCloud

JANUARY 3, 2025

We’ll cut through the jargon and provide practical advice on everything from discovering and onboarding new vendors to optimizing costs and ensuring security. By implementing these practices, organizations can optimize SaaS investments, mitigate risks, and ensure that vendors deliver value consistently. Book a d e mo.

Management

Kellblog

JUNE 1, 2025

While many sales skills are generic, you can save six to twelve months of onboarding time by hiring someone who has already sold to your target buyer. One day, when you’re huge, you may have to hire sales talent unfamiliar with your buyer and build an onboarding program to teach them. Such people exist. Go find one.

Sales Hiring

SaaStr

MAY 4, 2025

Heres where I think its heading based on 100,000+ conversations already on SaaStr’s own AI , and my experience investing in so many contact center and post-sales leaders: 1. It’s already fundamentally remade the contact center and post-sales. And it’s just getting there in sales.

AI

SaaStr

JULY 29, 2025

” This data-driven approach to enablement is helping companies optimize their onboarding and ongoing training programs. But they’re also being strategic about where they invest and how they implement. As one leader explained: “We’re growing so fast, bringing so many people in.

AI Search

SaaStr

JULY 18, 2025

I work with or have invested in dozens of AI companies. Almost every B2B AI company I work with and in my portfolio has a 30 day or so onboarding process, driven by humans. Enterprises buying AI are like your grandma getting an iPhone: they want to use it, but they need you to set it up. Want to know the dirty secret?

AI

User Pilot

JUNE 30, 2025

At times, even a great in-app onboarding flow isn’t enough. That’s where an onboarding email sequence comes in. In this guide, I’ll show you 8 onboarding email types that drive activation, with real examples and templates you can use. Together, these email examples can serve as a blueprint for your customer onboarding sequence.

Onboarding

USIO

JUNE 9, 2025

At its core, a Payment Facilitator is a master merchant that onboards and manages sub-merchants under its own payment umbrella. In plain English: You, as the platform, take full responsibility for underwriting, onboarding, monitoring, and settling payments for your customers. First, What Is a Payment Facilitator (PayFac)? With PFaaS?

Payment Services

ChurnZero

FEBRUARY 28, 2025

Take a page from your B2C counterparts and optimize for onboarding , engagement and retention. 3: Make onboarding seamless. Build onboarding, engagement and expansion right into your products. Build onboarding, engagement and expansion right into your products. 2: Leverage data to drive more personalized experiences.

SaaS Payments

Stax

JUNE 3, 2025

Scales with your business Whether you’re onboarding your first customer or your thousandth, SaaS platforms can grow with you. Built-in security Leading SaaS providers invest heavily in security infrastructurefar beyond what most businesses could implement on their own. No more manual downloads or downtime.

Payment Services

ChurnZero

MAY 23, 2025

Even if you’re crushing expansion targets, weak GRR indicates foundational problems – often in onboarding, support, product adoption, or customer alignment. It also gives you a view into which segments drive the most margin and which may need more investment or a change in strategy. It shows your pure retention rate.

Customer Success

User Pilot

JANUARY 19, 2025

At first, this seemed like a smart investment for my company, so I invested. Reasons why you shouldn’t invest in standalone session recording tools You might think standalone session replay tools have one flaw, but theres more to the story. Reasons for not investing in standalone session recording tools.

Investment