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The Top 10 Product Leadership Lessons from Plaid’s and Brex’s Presidents Product leaders often ask me what it takes to build successful products in the age of AI, especially in fintech where the stakes are incredibly high. At SaaStr Annual we recently had the chance to do a dive deep with Jen Taylor (President, Plaid) and Karan Nangia (President, Brex) on this exact topic.
My feeds in social media are filled with Cheatsheets, Hacks, Templates—all sorts of tools. They attract lots of interest, lots of requests. People are looking for anything they can do to help them do their jobs, to find the shortcuts or secrets to success. I look at them, most are pretty good, there are always interesting ideas and approaches.
Matt from Grand Rapids says, If I dont make my cold calls, our pipeline will go dry. He is juggling everything from operations to customer service escalations, all while trying to generate fresh leads through cold calls. Sound familiar? In this Ask Jeb segment of the Sales Gravy Podcast I walk Matt through practical strategies to carve out time for prospecting and target the right prospects so that he can keep his sales pipeline fulleven while being pulled in a dozen directions.
By Maria Geokezas , Chief Operating Officer at Heinz Marketing AI is rapidly transforming sales and marketing, and one area getting a lot of attention is AI-powered Business Development Representatives (BDRs). But what does that really mean? Are companies using robots to replace human reps? Can AI actually engage and qualify leads effectively? And most importantlydoes it work?
Speaker: Matt Sunshine, CEO at The Center for Sales Strategy
AI isn’t replacing salespeople—it’s empowering them. The most forward-thinking sales organizations are using AI to enhance human performance rather than eliminate it. From coaching and messaging to prospecting and pipeline accountability, artificial intelligence is giving managers and SDRs the new tools they need to work smarter, sell better, and close more.
One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. All the questions still hold today, but I wanted to update them for 2025. It’s a different world today, AI-fueled, often distributed and hybrid, and with inflation both in titles (CRO or VP Sales) and compensation expectations. Use this updated script for hiring that first VP of Sales.
Key Takeaways Tailoring evaluations to specific sales roles ensures feedback fits the job, enhancing sales team performance where it counts. Employees who arent recognized are twice as likely to quit within a year, proving praise drives employee performance and retention. Regular performance reviews transform feedback into a growth tool. Sales performance evaluations often feel like a box-checking exercise for managers and a stress test for sales reps.
If youve hung around me for longer than five minutes, youve heard me say that sales is about talking with people. The fact is, the more people you talk with, the more youll sell. The good news is that there are lots of people to talk with. The problem is, far too many salespeople have quit talking with people. Email Prospecting Has Suddenly Stop Working Instead they keep prospects and customers at arms length through asynchronous communication channels like email - especially when prospecting.
If youve hung around me for longer than five minutes, youve heard me say that sales is about talking with people. The fact is, the more people you talk with, the more youll sell. The good news is that there are lots of people to talk with. The problem is, far too many salespeople have quit talking with people. Email Prospecting Has Suddenly Stop Working Instead they keep prospects and customers at arms length through asynchronous communication channels like email - especially when prospecting.
My first job out of college was one I made up. People become entrepreneurs for lots of reasons , and for me (like most) it was the flexible hours. Armed with an English degree and a basic knowledge of marketing, I started a small agency creating written content for anyone who needed it. I built a book of business by relying on my network and a surprisingly reasonable number of targeted cold emails.
How Rippling Built a Revenue Machine From Zero to Billions In a packed session at SaaStr Annual , Rippling CRO Matt Plank sat down with Sam Blond (former Brex CRO, now founder and also board director at Rippling) to break down exactly how Rippling scaled from zero to a $14B+ valuation and hundreds of millions in ARR. Contrary to the popular narrative that “outbound is dead” and “AI will replace sales,” Rippling has built a revenue juggernaut with a decidedly human-centric
This month, the Revenue Builders podcast shared some detailed breakdowns of complex sales processes, growth stages and leadership challenges. Seasoned Chief Revenue Officers shared insights on how they create process rigor to ensure their organization handles high-stakes deals with tact to maximize returns. From complicated deal negotiations, to identifying influential champions, to handling your board of advisors, these episodes deal with some of the biggest execution challenges facing revenue
This week, two separate conversations with CROs. Completely different markets/industries, both high performing in their segments. But they were deeply frustrated. “We’re struggling to make our numbers!” As we dove into it, their markets were OK, customers were still growing and investing. Then we dove into the data, pipelines very anemic, but win rates, average deal sizes, sales cycles were reasonable. “What are they doing to find and qualify new opportunities?
Speaker: Brendan Sweeney, VP of Global Sales and David Phelan, Account Manager
In a world where buyers are more informed and objections are more nuanced, confidence isn't optional—it’s a competitive advantage. In high-stakes conversations, knowing how to handle pushback can make or break the deal. Join industry experts Brendan Sweeney and David Phelan for a behind-the-scenes look at how teams are transforming sales coaching with real-time feedback, objection-handling role plays, and pre-call preparation that actually sticks.
Youre stalled. Youre stuck. Youve plateaued. No matter how you put it, youre seeing your sales hit a rut. And lets face it, youre in a rut, too. So, how do you pull yourself out of it? The answer: invest in yourself. The Power of Personal Development In sales, it's easy to get caught up in the grindcalls to make and deals to close. But if you dont make time to invest in yourself, sooner or later, youll hit a wall and fall into a rut.
Dear SaaStr: How Can a New VC Build Relationships With Top Founders? Screenshot Be where the founders are. Go to events, dinners, meet-ups, demo days, etc. Go where your prospects are. This always works. But you really have to hustle for this to work. A random cocktail party here or there is unlikely to work. Network with VCs a stage earlier than you or your peers.
In B2B, the account-based strategies that delivered results just a few years ago are now table stakes. In a world where buyers expect authentic, personalized experiences at every touchpoint, static target account lists, surface-level personalization and overreliance on third-party data no longer cut it. The truth is uncomfortable but necessary: Traditional ABM is becoming a commodity, not because it doesn’t work, but because everyone is doing it.
Artificial intelligence (AI) is transforming customer interactions, but success isnt just about technology its about the people behind it. Building a team well-versed in Agentforce skills ensures that your AI investments deliver real value. Heres how were doing it at Salesforce, and how you can too. Consider Your Use Case It all starts with understanding your Agentforce use case.
Speaker: Jady West, VP of Hospitality & Chris Bennett, Head of Sales & Engineering
The modern hotel room is no longer just a place to stay—it’s an experience to remember. Today’s guests expect seamless 5G connectivity, personalized comfort, and high-tech convenience. From AI-powered smart room controls to in-room entertainment and app-based services, technology is redefining hospitality from the inside out. In this new session featuring industry pros Jady West and Chris Bennett, we’ll explore how high-speed, high-bandwidth connectivity powers the innovations that are enabling
Hitting a wall with client callbacks? No worries. In this video I share three battle-tested techniques that’ll have your prospects eager to talk and move to the next step. Let’s … The post 3 Ways to Create Engagement first appeared on Colleen Francis - The Sales Leader.
David Frankel is Managing Partner at Founder Collective, a successful seed fund with investments in companies like The Trade Desk, Olo, and Coupang. With decades of experience as both a founder and investor, David brings a unique perspective to the often-misunderstood process of selling a company. He openly admits that many of his past exits were mistakes, which makes his advice on the topic particularly valuable.
We see it all the time our clients invest in HubSpot but barely tap into its AI capabilities. Its like buying a high-performance car and leaving it in the garage. If your team is still doing things the hard way, youre missing out on easy wins. HubSpots AI tools are making workflows faster and more efficient. From contact records to workflows, AI removes tedious tasks so you can focus on what really matters.
I speak with lots of leaders about their GTM strategies. My social channels are dominated by experts suggesting the GTM strategies. One of the things I’ve started doing is counting how many times they use the word, “Customer.” It’s surprising how seldom the word is used. When it is, it’s used in the context of the customer being the target of a set of strategies and activities.
Retailers know the clock is ticking–legacy SAP Commerce support ends in 2026. Legacy platforms are becoming a liability burdened by complexity, rigidity, and mounting operational costs. But modernization isn’t just about swapping out systems, it’s about preparing for a future shaped by real-time interactions, AI powered buying assistants, and flexible commerce architecture.
The GTM Podcast is available on any major directory, including: Apple Podcasts Spotify YouTube Jessica Gilmartin has nearly 20 years of go-to-market leadership experience, most recently serving as both the Chief Revenue Officer and Chief Marketing Officer at Calendly. Prior to that, she led marketing teams at an impressive array of companies, including Asana, Honor, Google, and Microsoft.
Codium is one of the fastest-growing startups in the AI coding assistant space, having scaled its go-to-market team from 3 to 75 in just under a year. Recently valued at over $1 billion , Codium is proving that AI-driven software development is not just the futureits the present. In our most recent episode of CRO Confidential , hosted by Sam Blond , Graham Moreno , VP of Worldwide Sales at Codium, shared invaluable insights on what drove this growth, the challenges they faced, and how other SaaS
Salesforce and Microsoft unveiled new AI sales agents yesterday, fueling a fiery corporate grudge match. Salesforce announced the upgraded Agentforce 2dx, while Microsoft introduced its AI Accelerator for Sales alongside new Sales Agent and Sales Chat agents. While all these tools aim to boost sales productivity and efficiency, they have distinctly different strategic approaches.
We reject the old and outdated sales approaches that are still being used by many sales organizations and their sales teams-as they are no longer effective in the third decade of the 21st Century. We recognize that most of B2B Sales Training is a rehashing of others work with a small number capable of creating a true paradigm in sales. We reject the idea that more is the way to improve sales results.
When culture isn’t consistently lived out across the organization, engagement suffers—and it often starts with a disconnect at the top. In this session, Beth Sunshine, SVP of Up Your Culture at The Center for Sales Strategy, will reveal how HR and executive leaders can close the gap between vision and execution by equipping frontline and mid-level managers to become culture carriers.
Key Takeaways RevOps frameworks streamline your technology stack, clean up CRM data, and get sales reps using sales tools. Choose or blend a framework to match your growth stage for steady, predictable revenue gains. 80% of companies with real-time analytics outperform peersRevOps makes this possible. Revenue Operations , or RevOps, is all about aligning your GTM teams (sales, marketing, and customer success) to drive growth.
So Snowflake looked immortal in 2021, looked a little more mortal in 2024 … and is now, like many of the best in Cloud and B2B, reacclerating in 2025! And come meet and hear from CEO Sridhar Ramaswamy LIVE at 2025 SaaStr Annual, May 13-15 in SF Bay!! Snowflake is on a tear again: $4B ARR (just about) 28% revenue growth 44% free-cash flow last quarter (WOW!
We think of cognitive biases as psychological shortcuts people use to process information and make decisions. You probably use these devices (e.g., loss aversion, the fear of missing out and social proof) in your email copy and design to persuade customers to engage and convert. These are positive uses of cognitive bias to increase the chance that customers will do what you want.
Building strong customer relationships is at the heart of every successful business. For startups and small to medium-sized businesses (SMBs) , the challenge often lies in managing those relationships efficiently as the company grows. Enter the customer relationship management (CRM) manager a professional dedicated to ensuring your CRM strategy and tools work effectively to support your business goals.
Documents are the backbone of enterprise operations, but they are also a common source of inefficiency. From buried insights to manual handoffs, document-based workflows can quietly stall decision-making and drain resources. For large, complex organizations, legacy systems and siloed processes create friction that AI is uniquely positioned to resolve.
My apologies as this is going to be long. I have now completed my first large scale test of the email marketing feature and I survived. I did run into a few bugs that are in the process of being squashed. This is why they call it beta testing. I sent the messages in groups of 500 so that I could easily monitor and manage the results. I sent some batches with both open and link tracking and others with link tracking only.
It’s your chance to catch up on the best and more popular from SaaStr this week! Top Posts: #1. The 2021 GTM Playbook Is Mostly Dead. But Whats The AI Era Replacement? #2. How AI is Really Changing SaaS From the CEO of Procore, co-CEO of Monday and Chair of HubSpot #3. Sapphire Ventures: VC Deals in B2B Start 2025 Down Another -8% #4. Is The Only Way to Get a Good Deal on a Renewal To Threaten to Leave?
Ecommerce may be thriving, but brick-and-mortar retail remains a critical brand touchpoint. Companies like Netflix and Wayfair are proving that physical stores arent just about transactions theyre influential brand ambassadors that shape perception and loyalty. The challenge is clear: How can brands create in-person experiences that draw people in and build lasting connections?
When we think about Digital Rooms, we see a tool with transformative potential, yet many organizations still struggle to adopt it fully. Some love the technology but question what “good” looks like in practice, while others view it as too much effort or are hesitant to break away from their current methods. This hesitation underscores a common challenge: understanding not only the benefits for sellers but also what customers are truly looking for in the experience.
B2B marketers face a number of challenges, including: continuously generating great leads converting leads to active sales prospects finding vendors that deliver real results Aggregage has proven content syndication, webinar, online advertising and intent signal marketing programs that deliver higher-quality leads. More than 700 companies have already benefited from our programs.
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