The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 761: How to Build Pipeline and GTM Alignment with Datadog's CMO Sara Varni

Sara Varni, Datadog's CMO, shares how to build pipeline and create alignment across sales and marketing. The CMO role at Datadog covers the usual aspects of marketing, including product marketing, corporate communications, events, partnership marketing, and solutions marketing.

While these insights seem like pipeline 101, they aren't always implemented. Let's look at some quick facts about Sara's experience. She spent a decade at Salesforce before moving on to Twilio as CMO when they were at about $400M ARR with 30 sales reps. They had a healthy self-service motion, but growth was flattening.

About four years later, she joined Attentive as CMO, a late-stage startup in the SMS marketing space. Now, she's the CMO at Datadog. Each of these companies had different GTM motions.

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Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code jason50 for an extra discount on our very best pricing.

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This episode is sponsored by: remote.com

When the right person for the job is a world away, Remote Talent brings the world to you. As the top job board for remote-first companies, we give you powerful tools to post your listings and reach the world's top candidates and remote professionals. Start building your dream team from anywhere—visit Remote.com/jobs today.

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This episode is sponsored by: Anrok

A question for SaaS finance leaders, do you know where your customers are? Anrok tracks where your sales are creating exposure, and automates tax calculation and filing worldwide. Built for high-growth software companies, Anrok protects your revenue and saves you time. Visit anrok.com/saastr to learn more.

SaaStr 760: CRO Confidential: Rippling's Top 3 Growth Tactics for Driving Revenue at Scale with Rippling CRO Matt Plank and Former CRO at Brex Sam Blond

At this year's SaaStr Annual, Rippling's CRO, Matt Plank, chats with Sam Blond, host of the SaaStr CRO Confidential and former CRO at Brex, about Rippling's top 3 growth tactics, which have led to the Rippling becoming a $14B company with several hundred million of ARR. A few years ago, Matt was making cold calls from CEO Parker Conrad's basement, and he's helped bring Rippling to where it is today.

The three growth tactics that worked for Rippling can be categorized into three different stages:

1. Outbound
2. Increasing closed-won revenue rates
3. Serving customers and expanding revenue in the base

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SaaStr hosts the largest SaaS community events on the planet.

Join us in 2025 at:

• SaaStr Annual: May. 13-15 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Get your early bird tickets TODAY.

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This episode is sponsored by: Pendo

This episode is sponsored by our good friends at Pendo the all-in-one product experience platform. Pendo brings together product analytics. Guides discovery and replay. So you can improve your product experiences for every customer and employee try Pendo for free at Pendo.io/saastr.

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This episode is sponsored by: remote.com

• Ready to expand into new markets with confidence? Remote's comprehensive HR suite propels your growth from the ground up. From setting up new entities and managing intellectual property, to overseeing contractor compliance Remote makes scaling effortless.With their platform and partnership, your business grows not just bigger, but smarter. Transform your growth today with remote at Remote.com.

SaaStr 759: 5 Metrics that Matter When Raising Your SaaS Series A and Series B Round with Christoph Janz, Partner at Point Nine Capital

What data and metrics do you need to convince SaaS investors you're in good shape and aligned with what they care about? Christoph Janz, Partner at Point Nine Capital, shares 5 key insights during this year's SaaStr Annual.

These metrics are more targeted to those preparing for a Series A or B round and could make the difference between an excited-to-invest-in-you investor and a pass. Why should you spend the time getting your act together before fundraising? If your data is self-explanatory, in good shape, easy to understand, and aligned with what investors care about, you avoid a lot of unnecessary back and forth.

Less time clarifying what your metrics mean results in more time to talk to more investors in parallel and increased confidence with each of those investors.

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SaaStr hosts the largest SaaS community events on the planet.

Join us in 2025 at:

• SaaStr Annual: May. 13-15 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Get your early bird tickets TODAY.

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This episode is sponsored by: Pendo

• This episode is sponsored by Pendo, the all-in-one product experience platform. Pendo helps your users do the things you really want them to do. You can try Pendo for free at Pendo.io/saastr and check out Mind The Product, the community for product people like… us.

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This episode is sponsored by: remote.com

• Big things start like this. Every industry leader began with a simple idea and the courage to dream big. At Remote, we're here to help you turn your vision into reality. From onboarding top talent to managing payroll worldwide, our tools and expertise support your journey from initial start to impressive growth worldwide. Start anywhere. Grow everywhere. Forge your path to success at Remote.com.

SaaStr 758: Avoid These Common Founder Mistakes to Hire a Great VP of Sales in 2024 with SaaStr CEO and Founder Jason Lemkin

In this episode of the official SaaStr podcast, we delve into the common pitfalls founders encounter when hiring a VP of Sales.

SaaStr CEO and Founder Jason Lemkin kicked off the SaaStr Annual by reflecting on twelve years of hiring lessons, sharing critical insights into why sales leaders fail and how founders can avoid these mistakes. The discussion covers the importance of due diligence, understanding the product, embracing sales involvement post-hire, and recognizing the signs of jaded or broken candidates.

The episode emphasizes the need for rigorous hiring processes and the impact of a bad hire on startup growth. Tune in for practical advice to ensure your next critical hire drives success.

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SaaStr hosts the largest SaaS community events on the planet.

Join us in 2025 at:

• SaaStr Annual: May. 13-15 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Get your early bird tickets TODAY.

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This episode is sponsored by: Pendo

• This episode is sponsored by Pendo, the all-in-one product experience platform. Pendo helps your users do the things you really want them to do. You can try Pendo for free at Pendo.io/saastr and check out Mind The Product, the community for product people like… us.

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This episode is sponsored by: remote.com

• Big things start like this. Every industry leader began with a simple idea and the courage to dream big. At Remote, we're here to help you turn your vision into reality. From onboarding top talent to managing payroll worldwide, our tools and expertise support your journey from initial start to impressive growth worldwide. Start anywhere. Grow everywhere. Forge your path to success at Remote.com.

SaaStr 757: 10 Cheat Codes I Learned While Scaling to $400M with Yext and Roam Founder Howard Lerman

Dive into a unique and tactical journey with Howard Lerman, Founder at Roam, sharing unconventional yet effective strategies drawn from personal experiences and notable figures like John Lennon. Learn the importance of mastering storytelling, the art of live demos, the controversial take on one-on-one meetings, and the benefits of Sunday night executive meetings. Discover how leveraging your cap table for strategic advisors can accelerate your business and understand the significance of maintaining product market fit. Embrace the philosophy of doing things your way and making your company an extension of your vision. This episode is packed with practical advice for startup founders looking to navigate the complexities of building and scaling their companies.

Howard's 10 cheat codes:

• Memorize Your Lines: Master storytelling by memorizing your company's story.
• The Live Demo: Take the risk with live demos.
• 1:1 Meetings Are Terrible: Avoid scheduled one-on-one meetings.
• Sunday Night Meetings: Start your week with Sunday night exec meetings.
• Advisor-Led Growth: Use stock options to bring on influential advisors.
• 5-Minute Meetings: Hold short, effective meetings.
• Meet with Customers: Meeting customers lifts spirits.
• Board Chair: Have a powerful chairperson.
• Do Not Delegate: Retain control over critical functions like product-market fit.
• Have Fun: Make your company your creative canvas.

SaaStr 756: From Challenges and Churn to Triumph - How to Deliver Exceptional Customer Support at Scale with Monday.com's VP of Customer Experience

In this episode of the Official SaaStr Podcast, Natalie Margolin, VP of Customer Experience at monday.com, shares her journey and strategies for enhancing customer experience in a rapidly growing company. From tackling challenges of scale, implementing AI and chatbots, to ensuring customer satisfaction and building an expert support team, Natalie explains the transformative steps and guiding principles that have positioned monday.com as an industry leader in customer experience.

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SaaStr hosts the largest SaaS community events on the planet.

Join us in 2024 at:

• SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20

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This episode is sponsored by: Paragon

• Are you constantly saying no to your customers' integration requests? You're not alone. That's why companies like Copy.ai and Sinch use Paragon, an embedded integration platform, to ship integrations 7 times faster. Ready to scale your product's integration strategy? Visit useparagon.com/saastr to explore how Paragon can help you go-to-market faster with integrations today.

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This episode is sponsored by: remote.com

• When the right person for the job is a world away, Remote Talent brings the world to you. As the top job board for remote-first companies, we give you powerful tools to post your listings and reach the world's top candidates and remote professionals. Start building your dream team from anywhere—visit Remote.com/jobs today.

SaaStr 755: How to Optimize Sales Performance, SaaStr CEO Jason Lemkin Answers Your Top SaaS Sales Questions

In this episode, we dive into the intricacies of effective sales check-ins, best practices for managing remote teams, and the essential strategies for hiring and ramping up sales leadership. Jason Lemkin answers audience questions, covers why Quarterly Business Reviews (QBRs) are becoming obsolete, the significance of measuring sales team activities, and the critical importance of ensuring new hires are product experts before they start. Other key topics include handling lone wolf sales reps, sourcing pipeline percentage, and the differing approaches needed for SMB and enterprise sales teams. A must-listen for SaaS founders, sales leaders, and anyone looking to optimize their sales process in our remote-first world.

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SaaStr hosts the largest SaaS community events on the planet.

Join us in 2024 at:

• SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20

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This episode is sponsored by: Paragon

• Are you constantly saying no to your customers' integration requests? You're not alone. That's why companies like Copy.ai and Sinch use Paragon, an embedded integration platform, to ship integrations 7 times faster. Ready to scale your product's integration strategy? Visit useparagon.com/saastr to explore how Paragon can help you go-to-market faster with integrations today.

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This episode is sponsored by: remote.com

• Elevate your contractor management with a platform built for SaaS leaders. With Remote, you get zero-cost compliance screening and a fair price guarantee from day one. Enjoy fast, international payments, round-the-clock support, and robust indemnity coverage with Contractor Management Plus. Scale your operations confidently with Remote.com—visit us to start your free 30-day trial and unlock a solution that simplifies end-to-end contractor management.

SaaStr 754: 7 Things the Best Sales Reps Get Right and 8 Ways the Rest Make Things Worse with SaaStr CEO and Founder Jason Lemkin Join Jason Lemkin, in this insightful episode as he dives deep into distinguishing the best sales reps from the rest. Jason outlines seven key traits that make sales reps successful, such as understanding customer problems, facilitating product demos, and being honest about competition. He also discusses common pitfalls that mediocre sales reps fall into, including playing endless games with pricing and creating urgency without value. Perfect for founders, sales leaders, and team managers looking to improve their hiring process and team efficiency, this episode offers practical, real-world examples and strategies to implement right away.

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SaaStr hosts the largest SaaS community events on the planet.

Join us in 2024 at:

• SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20

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This episode is sponsored by: Paragon

• Are you constantly saying no to your customers' integration requests? You're not alone. That's why companies like Copy.ai and Sinch use Paragon, an embedded integration platform, to ship integrations 7 times faster. Ready to scale your product's integration strategy? Visit useparagon.com/saastr to explore how Paragon can help you go-to-market faster with integrations today.

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This episode is sponsored by: remote.com

• When the right person for the job is a world away, Remote Talent brings the world to you. As the top job board for remote-first companies, we give you powerful tools to post your listings and reach the world's top candidates and remote professionals. Start building your dream team from anywhere—visit Remote.com/jobs today.

SaaStr 753: Unveiling the 2024 CRO Playbook, How to Navigate A Shifting Sales Environment with Salesloft's CRO Mark Niemiec

In this insightful podcast, Mark Niemiec, the CRO of SalesLoft, shares his strategic approach and key lessons learned since joining the company in February.

Drawing from his extensive experience at Salesforce and Cisco, Mark discusses the challenges and opportunities that come with onboarding as a new CRO, especially in dynamic market conditions. He emphasizes the importance of vision setting, strategic planning, and effective communication. Mark also provides practical tips on customer engagement, team dynamics, and the significance of maintaining a balanced work-life routine. Whether you're a founder, sales leader, or aspiring CRO, this episode offers valuable actionable insights for driving successful change in your organization.

SaaStr 752: 9 Signs a Startup Isn't Going to Make It with SaaStr CEO and Founder Jason Lemkin

SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn't going to make it. We all know, we're living in strange times.

• A lot of AI companies are growing 500% a year and exploding
• A lot of public leaders are struggling
• Some unicorns are doing incredibly well, while others have stalled and are growing at zero

Founders are struggling with how to deal with these changes, and VCs and executives are trying to decide if companies are worth joining, investing in, or sticking it out with. It's nuanced.

So, let's look at the nine signs a startup will fail. As leaders, if you see yourself doing some of these things, maybe it's time to stop it.