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Like so many of you, I enjoy the work of the worlds best comedians. At Anthony Cole Training Group, we have often used athletes, singers, and actors as a source of learning and inspiration for salespeople. And today, I want to add to that list by talking about sales tips and tactics that can be learned from comedians.
There is so much conversation about win rates. But in those conversations, there’s a lot of misunderstanding. What we measure, how we measure it, varies tremendously. Some measure win rate from very first contact. Some measure it from the moment of qualification. Some measure it on a $ basis some on a deal basis. Some attribute measure win rates within live deals, some look at past deals.
Ask Jeb: How to Sell When Your Customer Has to Sell First Welcome to another Ask Jeb segment on the Sales Gravy Podcast! Im Jeb Blountbestselling author of Fanatical Prospecting, Objections, Sales EQ, and INKED. In each of these special episodes, we shine a spotlight on your questions, challenges, and roadblocksoffering real-world advice from sales pros who are in the trenches every single day.
Activant Capital brought together at SaaStr Annua l a group of break-out next-generation AI enhanced vertical software leaders: the CEOs from Owner.com, Alloy Automation, and DoNotPay. At SaaStr Annual they shared their experiences and insights on implementing AI in vertical software companies. Adam Guild, CEO Owner Adam Guild leads Owner.com, a comprehensive platform helping restaurant owners succeed in the digital space.
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.
SaaS pricing isn’t static – it’s a living strategy that grows with your company. In this article we dive into a playbook for pricing across different stages of company growth, inspired by Geoffrey Moore’s Crossing the Chasm. Each growth stage demands its own pricing approach, and getting it right can mean the difference between stagnation and explosive growth.
I’ve been doing some work with a brilliant CRO. We’ve been reworking and implementing a revised selling/buying process. Their previous process was poorly defined, outdated, and people weren’t using it. As we are rolling this out, she is encountering resistance from her team: “My situations are all different! This is too rigid!
On this first Monday of the second month of the year its time for a gut check. First we need to check where we are against our new year goals. Next we need to take stock of our first month sales performance and make adjustments. Were just a little more than thirty days away from our new year intentions, resolutions, and goals. A month ago we set out into the new year with hope and ambition that this year would be our best ever and that wed make positive lasting changes in our lives.
On this first Monday of the second month of the year its time for a gut check. First we need to check where we are against our new year goals. Next we need to take stock of our first month sales performance and make adjustments. Were just a little more than thirty days away from our new year intentions, resolutions, and goals. A month ago we set out into the new year with hope and ambition that this year would be our best ever and that wed make positive lasting changes in our lives.
Dear SaaStr: How Do The Best Sales Leaders Retain Their High Performers? A few ways Ive observed that the best sales leaders retain the best: They promote the best. You cant promote everyone, but you can almost always promote your best. They make them better. They help make sure their biggest deals close. Even more than usual. They have fun together.
Want AI search engines and agents to find and use your content? Traditional SEO isnt enough. AI systems process information differently. This guide breaks down key optimizations to help your content stay visible and rank in the AI era. TL;DR: Quick AI optimization checklist To optimize for AI search and agents: Make content accessible with clean HTML/markdown and good structure.
AI isn’t here to steal your job but to make it easier. Here are practical ways to harness AI’s power. For more strategies like this, check out my sales tip … The post Practical Use of AI in Sales first appeared on Colleen Francis - The Sales Leader.
Is your website truly working as hard as your sales team? In todays competitive digital landscape, your website isnt just an online brochureit can be one of your best salespeople. Podcaster and influencer Sam Dunning joins The Sales Gravy Podcast to discuss the Caveman Grunt Website Test, why effective SEO strategies are never a one-and-done exercise, and how to build and how to maximize website performance for consistent sales growth.
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.
The Real Truth About AI Data Privacy in 2025: What Every SaaS Company Needs to Know The explosion of AI adoption has created massive new privacy risks for SaaS companies. Here’s what we learned from talking with Skyflow’s Chief Product Officer about protecting your company (and your customers) from AI data breaches: AI and data privacy. Not the fluffy marketing version – the real, nitty-gritty details that determine whether your SaaS company thrives or dies in the AI era.
In the fast-paced world of tech sales, staying ahead of the curve is crucial. As we step into 2025, sales strategies are being reshaped by shifting economic conditions, expanding buying committees, and the integration of new technologies. In the latest episode of our podcast, we dive deep into these changes with Matt Green , CRO and co-founder of Sales Assembly , to uncover the essential skills and strategies that sales professionals need to thrive in this evolving landscape.
In the past few days, I’ve heard two fascinating things. At first, they seem very different, but when you think about them, the underlying issues are similar. The first was was a quote from Tom Mendoza on The Learn-It-All podcast, “Nothing great has ever been done by people that don’t want to do it!’ The second was in a conversation with Brent Adamson.
Ever wondered if your Mac mini M4 Pro could become an LLM powerhouse? The short answer: not exactly but it can run DeepSeek R1 models locally without relying on cloud-based AI servers. Here’s how to set it up using Docker and Open WebUI for a seamless, ChatGPT-like experience while keeping your data private and under your control. With the right configuration, your Mac mini can handle fine-tuning, text generation and retrieval tasks without needing a dedicated server.
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
When I look at the VP of Sales / CRO that didnt work out the past 12-18 months across the SaaStr Fund portfolio and my ecosystem, one thing stands out. And its an old SaaStr theme: #1: You have to hire folks in sales where their last job was harder. There may exceptions at rocketships. When market pull is incredibly strong and your brand is #1, just hiring experienced folks may be enough.
For years, organizations have relied on traditional Finance for the Non-Financial Manager (FFNFM) programs to help managers better understand essential financial concepts and terms. This allows them to understand how their company makes money and, possibly, how to make better business decisions. In fact, a recent Advantexe survey found that 76% of companies still offer an FFNFM program, proving its continued relevance.
Unlock the secret sauce to boosting your closing rate with team selling. Dive in to discover how bringing a colleague along can be the smartest move you make this year. … The post Ready to Close 30% More? first appeared on Colleen Francis - The Sales Leader.
Choosing the right paid media channels is key to B2B advertising success. This guide covers the best PPC platforms — Google, LinkedIn , Microsoft, and more — plus expert tactics to reach decision-makers and drive results. 1. Google Search Google is an effective way to reach B2B decision-makers when they are actively searching. But how do you ensure you’re reaching someone truly looking for a food supplier for their restaurant and not just Joe Schmoe craving a steak dinner?
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.
In the latest episode of SaaStr’s CRO Confidential Series, our host Sam Blond sits down with Ron Gabrisko, CRO of Databricks , to unpack the journey from $1M in ARR to crossing $3B ARR at the end of January 2025. With Databricks now one of the largest pre-IPO technology companies, with $10 billion of expected non-dilutive financing and a valuation of $62 billion, Ron’s insights are gold for any revenue leader looking to scale.
By Carly Bauer , Marketing Consultant at Heinz Marketing Short-Term Wins and Long-Term Growth Too often, the pressure to drive short-term demand leads companies to neglect the foundational work required to build a lasting brand. However, a strong brand story isnt just about long-term reputationit plays a crucial role in generating demand today and setting up sustainable growth for the future.
If youre looking for new ways to increase your sales, you may be considering subscription-based products or services. Subscriptions help you earn long-term income from customers instead of relying on infrequent or sporadic purchases. You can learn from other business models requiring monthly payments, like car insurance for different types of drivers , to see what you could carry over to your business.
Look at your marketing stack. That sprawling collection of tools tells a story of ambition, necessity and maybe a little FOMO. Some 14,106 martech solutions are competing for your attention, a staggering 27.8% jump from the prior year. They overlap. They collect dust. They refuse to play nice with each other. And every month, another vendor pitches you the next game-changing solution to a problem you’re not sure you have.
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.
Dialpad’s Top Learnings Building Its Own AI Stack When it comes to AI implementation in SaaS, most companies are still figuring out whether to build or buy. But Dialpad has been quietly building their AI advantage for over 7 years, processing more than 8 billion minutes of conversations and hitting $300M ARR along the way. At SaaStr AI Day 2025, Jim Palmer, Dialpad’s Chief AI Officer (and co-founder of TalkIQ, which Dialpad acquired), shared the tactical playbook they used to build a
In todays uncertain economic environment, businesses need to find ways to do more with less. On AppExchange, you can do that by using Flows and Collections. Flows bring time-saving automations and capabilities to the apps you already use, and Collections provide an efficient way to find multiple, similar problem-solving apps. Both make your work processes more efficient, allowing your teams to reach new levels of productivity.
Hello and welcome to The GTM Newsletter by GTMnow – read by 50,000+ to scale their companies and careers. GTMnow shares insight around the go-to-market strategies responsible for explosive company growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind these strategies and companies. 7 CRO tips for smarter annual planning 1.
Your customer base is the single greatest determinant of your future success. In the competitive world of B2B, youre in a race for profitability. Your technology might give you a temporary edge, but competitors will catch up. What truly sets you apart is your ideal customer profile (ICP). Done right, its your catalyst for sustainable growth, propelling you to long-term profitability and customer success.
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.
"How @stripe Began to Target Enterprise Buyers" with CBO @jdewitt29 : 1Picked 30 names to win 2Built small Lighthouse Dev Team to do work 3Dev team came into every sales call 4Needed add solutions team pic.twitter.com/qNf3MhlayI — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) January 31, 2025 Want to know when to move upmarket and how to actually pull it off?
For the past century, oil and gas companies have shown an inherent resilience. They have rebounded and adapted to geopolitical, social, and environmental forces while maintaining a powerful role in the global economy. Now, the industry is at another pivotal moment: It can no longer rely on steady growth as the world seeks to reduce its carbon footprint.
Driving successful go-to-market initiatives is no easy featand once launched, understanding how theyre performing can often feel like a guessing game. In fact, 90% of organizations fail to implement their strategies successfully, which often comes down to a lack of consistent execution. This execution gap is a major barrier to growth, largely driven by disconnected teams working in silos.
Customer engagement and experience (CX) are in the midst of yet another big shift thanks to new technology and changing customer behaviors. So businesses are turning to AI to personalize interactions, boost satisfaction and improve efficiencyall while driving revenue. Two recent reports provide important insights into todays CX landscape, investment trends and AIs growing role.
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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