SaaStr 713: Why the Future of Customer Success, Sales and Marketing Has Changed: Ask-Me-Anything Part 2 with SaaStr CEO and Founder Jason Lemkin

In part one of this Ask-Me-Anything (AMA) with SaaStr founder and CEO Jason Lemkin, he answered the community’s questions about whether all anyone cares about is AI anymore, investor appetites going into 2024, vertical SaaS, and thriving as a solo founder.

In part two we head into IPO waters, how to incorporate AI into your products, the best way to drive employee performance, pricing models, and why the future of roles in customer success, sales and marketing have forever changed in SaaS. 

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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
• SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave200

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This episode is sponsored by: Northwest Registered Agent

When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

As AI continues to reshape the way businesses operate, it has become a critical differentiator in gaining a competitive edge. Stage 2 Capital Co-founder and Managing Director Mark Roberge dissects the advantages and challenges faced by both startups and incumbents in leveraging AI for Go-to-Market strategies. Uncover the unique capabilities that startups bring to the table and how they disrupt established players with their agility, innovation, and ability to adapt to changing market dynamics.

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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=fave50
• SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave20

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This episode is sponsored by: Northwest Registered Agent

When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

Welcome to Part Two of SaaStr founder and CEO Jason Lemkin’s Ask Me Anything session at this year’s SaaStr Annual.

Jason re-takes the stage in Part 2 of the series to answer questions about the right time is to invest in a new product line, building vertical vs. horizontal, multiples in 2024, and much more. 

Building and scaling a startup isn’t for the faint of heart and often comes with many ups and downs that SaaS veterans have experience in. 

So, let’s jump right into Part Two. 

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This episode is sponsored by: Northwest Registered Agent

When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

Discover how three breakout SaaS companies scaled from an idea to hundreds of employees and $1B+ valuations, all while living their values along the way. 

Notion COO Akshay Kothari, Motive CEO and Founder Shoaib Makani, and CEO and Co-Founder of Incredible Health Iman Abuzeid share the secrets of ensuring their company-centered values and purpose remained an anchor amidst hypergrowth.  Moderated by Laura Weidman Powers, Operating Partner at Base10 Partners.

As we dive into these three highly successful companies, we’ll talk about their values, the process of creating them, and the right time for founders to create their own values. 

Are you trying to unlock sustainable low customer acquisition costs (CAC) growth for your SaaS company?

Then you need to hear what Guillaume Cabane, Co-Founder and President of HyperGrowth Partners, has to say on the subject. In this podcast, Guillaume shares the formula he used at Ramp, Gorgias, and Drift to reach explosive saas growth - showing you the secrets of smart scaling.

 Don't miss out - listen now now for groundbreaking advice on generating fast CAC growth success!

Founders of 2023 ask themselves, “What does it take to raise money right now in this uncertain market environment?” Peter Specht, Partner at Creandum, shares a data-driven perspective and real-time insights into the market of very recent rounds and current VC expectations. 

Unfortunately, raising money isn’t the same as raising in 2021. Specht walks you through what has happened in the last 12 months and the best practices for today. 

Some SaaS and Cloud leaders have seen big impacts from the post-Covid hangover, but others keep accelerating. MongoDB is one of those that has never stopped. 

Instead of looking at those who are struggling, let’s take a look at the epic growth story of MongoDB, a company crushing it in 2023. 

MongoDB is at a stunning $1.5B in ARR, 29% overall growth, and is worth $29B. That’s about as good as it gets in SaaS and Cloud! 

While many less efficient public SaaS companies are trading at tough multiples of 3-4x ARR, and the average is about 6x ARR, MongoDB is almost 20x ARR. 

Let’s look at nine interesting learnings about this leading company.

2023 has been a difficult year for many tech companies. Markets have been all over the place, layoffs occurred, and investors weren’t funding as much as usual. However, Sam Blond, Partner at Founders Fund & Host of the SaaStr CRO Confidential Podcast, believes there are reasons to be optimistic for the rest of 2023. In a special workshop, Sam shares advice on how to spot bottlenecks, reallocate the right resources, and grow revenue in 2023.  SaaStr Workshop Wednesdays are LIVE every Wednesday. Sign up for free. 

Many people at this year’s SaaStr Europa wondered about the future of customer success, motivation during hard times, and how to grow in this new era of efficiency. 

SaaStr CEO and Founder Jason Lemkin sat down with the audience for an Ask Me Anything session to answer some of the most pressing questions from the audience. 

If you missed part 1, catch that here.

First up is a bootstrapped founder looking for advice in today’s market. 

Startups come in all shapes and sizes on various stages of a timeline, yet it’s not surprising how many have the same questions and concerns about how to scale from x to y to z, the right time to hire and fire, and how to keep a team motivated during hard times. 

At this year’s SaaStr Europa, Jason Lemkin, CEO and Founder of SaaStr, took the stage to answer the audience's most pressing questions about the present and future of startups. 

His answers didn’t disappoint.

Retention is the new acquisition.

This paradigm shift has placed Customer Marketing in the spotlight as a pivotal function that helps companies achieve robust NRR metrics. Despite the revenue impact, Customer Marketing teams remain relatively lean and often struggle to secure the necessary support from cross-functional teams. Companies that have successfully unlocked the potential of Customer Marketing have seen a substantial increase in revenue.

Join Insider's Co-founder and CEO, Hande Cilingir, and CMO, Merve Nazlioglu, as they unveil ten game-changing tactics to accelerate your customer marketing programs on the path to achieving an outstanding 140% NRR.

Struggling to find product market-fit?

Join former Divvy CRO, Sterling Snow, and learn how the company went from 0 to a $2.5B exit in just four years using effective go-to-market strategies. Find out what the team did differently that set them apart from their competition and get your product off the ground in no time!

 There are 6 primary operating models Divvy used to fuel incredible growth, culture, and results. The best part is they're dead simple and every team should be using them. Don't miss this session where Sterling will talk through the tactics, mistakes, and lessons learned.

The rapid proliferation of cloud services has added to overwhelm among enterprise workers. Over the years, Grammarly has learned effective strategies to stand apart with users and business decision-makers while channeling customers’ needs, whether in customer support, sales, HR, and marketing. CEO Brad Hoover shares the customer-centric principles and lessons that he has learned in growing their user base to tens of millions of enterprise and individual customers, with teams from Accenture to Zoom.

Full video: https://youtu.be/zoyxXSYeZhM

Want to join the SaaStr community? We're the 🌎largest community for B2B software.

Subscribe for weekly updates: https://www.saastr.com/subscribeform

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To celebrate 10 years of SaaStr, we’re revisiting some classic podcast episodes. Up today: Harry Stebbings interviews Shippo Co-Founder and CEO Laura Behrens Wu. In April 2016, Shippo had only 22 employees and was just beginning to scale. They've since opened new hubs in Austin and Dublin and in 2021, hired Employee number 200.

Want to join the SaaStr community? We're the 🌎largest community for B2B software.

Subscribe for weekly updates: https://www.saastr.com/subscribeform

Twitter: https://twitter.com/saastr

LinkedIn: https://www.linkedin.com/company/2724976

Quora Group: https://www.quora.com/q/cloud

Facebook: https://www.facebook.com/SaaStr/

Instagram: https://www.instagram.com/saastr/

Our North American Event: https://bit.ly/2OXeAYh

Our European Event: https://bit.ly/2OZTad8

Mark Roberge is the Managing Director at Stage 2 Capital, Sr. Lecturer at Harvard Business School, and author of the bestselling book, The Sales Acceleration Formula. In this podcast, he'll outline some of the most common SaaS sales potholes when scaling from $0 to $100 million and how to avoid them.

Blog post & video: https://www.saastr.com/the-most-common-saas-sales-potholes-and-how-to-avoid-them-with-mark-roberge-podcast-498-and-video/

Sponsors:

https://shortcut.com/saastr

https://www.litmus.com/saastr

https://flatfile.com/saastr/

Chime wasn't the first digital bank, but it has become the largest one in the United States. In this episode, hear from Chris Britt, co-founder, and CEO, about Chime's journey in a highly competitive market and what it took to win.

Video + show notes: https://www.saastr.com/ringing-the-bell-on-competition-with-chime-ceo-chris-britt-and-satya-patel-homebrew/

Sandi Lin, CEO of Skilljar, shares how she successfully hired her first CRO. Then we will take an inside-out view and hear from Kathy Lord, CRO of Skilljar, about being the first CRO and what it really means.

Video + blog post: https://www.saastr.com/how-to-hire-your-first-chief-revenue-officer/

As Head of Experience Research at Asana, Beth Toland will share different ways to make customer insights a deep part of product development and strategy from ideation to delivery.

Video + blog post: https://www.saastr.com/asana-product-development-strategy/

In today's SaaStr podcast, SaaStr CEO and Founder, Jason Lemkin shares 5 interesting learnings from UiPath at $600m in ARR.

Video + blog post: https://www.saastr.com/5-interesting-learnings-from-uipath-at-600000000-in-arr/

Chen Amit is the Founder & CEO @ Tipalti, the only global payable automation platform that scales with you and now remitting $5Bn annually across 3M suppliers. To date, Chen has raised over $146M with Tipalti from the likes of Oren Zeev, Dan Rose, Mike Chalfen and then Greenspring, Truebridge and 01 Advisors to name a few. Previously, Chen was CEO of Atrica, acquired by Nokia-Siemens. He also was co-founder and CEO of Verix. At ECI Telecom, Chen founded its ADSL business unit and led it from inception to $100 million in annual sales. 

 In Today’s Episode We Discuss:

• How Chen made his way into the world of SaaS and came to found the leader in account payables with Tipalti?
• Why does Chen believe so much of his success is derived from saying no to customers? How does Chen determine which customer feedback to ingest vs to reject? If rejected, how can startups do this in a polite and respectful way? How can startups give the appearance of a large company to enterprises?   
• Given the infinite supply of capital, how does Chen think about unit economics? How does Chen think the right way to calculate LTV is? Where do many go wrong? What can we learn from Amazon when it comes to LTV? How does Chen advise founders to think about annual dollar churn? 
• How does Chen think about optimising pricing models today? How can SaaS companies have variable pricing mechanisms without disincentivizing usage? How does Chen think about aligning revenue scale to your customers? How can this be done? What are the benefits?  

Chen’s 60 Second SaaStr:

1. What is the hardest element of Chen’s role today with Tipalti?
2. What would Chen most like to change in the world of SaaS today? 
3. What does Chen believe that most around him disbelieve? 

Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-358-with-tipalti-founder-ceo-chen-amit/

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

The future of work is here and digital automation is now essential for today’s workforce. Tools have improved, but companies are STILL using outdated and manual processes to conduct business. Enter Pipefy. Pipefy is a workflow management software that makes business processes such as purchasing, onboarding, and recruiting—hassle-free, so requesters, processors and managers are more efficient. Pipefy seamlessly integrates with other tools in your toolchain to ensure a completely automated experience with a low to no code implementation. Dispersed or remote team members? NO PROBLEM! Pipefy can automate your requests from anywhere. Scroll over to pipefy.com/saastr to try it out and get 10% off your first 3 months. Empower your teams everywhere with Pipefy.

Sara Varni is the CMO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Sara, prior to Twilio she spent 10 years with Salesforce in numerous roles including SVP of Marketing for Salesforce’s Sales Cloud and CMO @ Desk.com, among other roles. If that wasn’t enough, Sara is also an advisor @ Anthos Capital.

In Today’s Episode We Discuss:

• How did Sara made her way into the world of SaaS and came to be one of the industry’s leading CMOs with Twilio today? What were Sara’s biggest takeaways from her 10 years at Salesforce seeing the incredible hyper-growth first hand?
• What does Sara mean when she says, “you have to have a creative plan to get your message to market”? Does Sara really believe that there is a playbook when it comes to marketing? How does Sara determine when to throw the playbook out of the window? What resounding question do you always have to ask yourself when thinking messaging?
• Messaging is very dependent on the customer being targeted, how does the messaging need to be different when targeting SMB vs enterprise? How does the creative plan to get the message to the target customer change dependent on SMB vs enterprise? Where does Sara see most people go wrong here?   
• Why does Sara so strongly believe in the power of customer stories? What makes the very best customer stories? What would Sara’s advice be to someone who is wanting to start creating them? Where does Sara see so many people go wrong? What are Sara’s tips for creating this alignment between the marketing team that make the stories and the sales team that sell them? Where are there often points of tension?
• What does the very commonly used term, “enablement”, really mean to Sara? Does it mean you can hire lower quality candidates and upgrade them? How does Sara distinguish between a stretch VP and a stretch too far? What questions does Sara find most revealing in the interview process?  

60 Second SaaStr:

1. What does Sara know now that she wishes she had known at the beginning?
2. Who is crushing it in the world of SaaS marketing today?
3. What is the most common reason for the breakdown of an efficient funnel?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sara Varni

Godard Abel is the Founder & CEO @ G2, the company helping millions of business make better product buying decisions every month. To date, Godard has raised over $100m in funding with G2 from the likes of Accel, IVP, High Alpha, Pritzker Group and Chicago Ventures just to name a few. As for Godard, he founded his first business, BigMachines, in 2000, a business he scaled to $50m in revenue and over 300 people up until it’s acquisition to Oracle 11 years later for $400m. Godard then became CEO @ Steelbrick where he took them from 5 to 200 employees and increased bookings by 37x in 7 quarters. Steelbrick was ultimately acquired by Salesforce where he spent a year and a half before starting G2.  

In Today’s Episode We Discuss:

• How did Godard make his way into the world of SaaS over 20 years ago? What was the a-ha moment for the founding of G2 for Godard?
• Having been a Founder through the bust of 2000, how did seeing that macro environment impact his operating mentality today? What did it teach him about capital efficiency and investing ahead of time? Taking the team from 70 to 20, what were his lessons on the right way to let someone go? Where do many people get it wrong today?     
• Why does Godard advocate for working with people that you have worked with before? How can you find the zone of genius for the people that you work with? How does Godard set a culture of ambition and determination around goals but also prevent dejection if the goals are not hit? How often should rep quota be hit? Why is that the right ratio?    
• Where does Godard believe that things really start to break down in the scaling of an organisation? What can you do to get ahead of those moments and minimise their impact? How many direct reports does Godard believe is the optimal and then the maximum for a manager to have? How have his thoughts on this changed over time?

Godard’s 60 Second SaaStr:

1. What would Godard like to change in the world of SaaS today?
2. What does Godard know now that he wishes he had known at the beginning?
3. If an investor can provide one value, what would it be and why?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Godard Abel

Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft’s emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic.

In Today’s Episode We Discuss:

• How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft?
• How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel?
• Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR’s 99% of the time not able to carry leads to completion?
• How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
• Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this?  Why does Manny believe that you should not have a VP before $5m?

60 Second SaaStr:

1. What does Manny know now that he wishes he had known in the beginning?
2. What does the future of sales prospecting look like to Manny?
3. What would Manny like to change about the world of SaaS today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Manny Medina

Qualtrics Co-Founder and CEO Ryan Smith sits down with SaaStr Founder and CEO Jason Lemkin as Ryan reflects on the survey software maker's acquisition by SAP this year. The company was acquired this November in an $8B deal ahead of its planned IPO. This is SaaStr’s founder favorites series where you can hear some of the best of the best of SaaStr Annual’s Speakers.

Missed the session? Here’s what Jason and Ryan talk about:

• Why did Qualtrics turn down a $500M acquisition offer in 2012?
• What did Qualtrics’ path to fundraising look like?
• How to build lifelong customers
• Capital efficiency (and dilution)

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $24m including the likes of Insight Venture Partners, Tiger Global and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 200 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India.

In Today’s Episode We Discuss:

• How Krish made his way into the world of SaaS and came to found one of India fastest growing SaaS companies in Chargebee?
• Why does Krish believe that every SaaS company should bootstrap at some stage? What are the inherent benefits to these capital constraints? What are the drawbacks to not having the capital reserves? What was the inflection point for Krish in realising he wanted to go big and raise from Insight?  
• Why does Krish believe that it is wrong to think of the word “service” as being negative in SaaS? What are some of the foundational benefits to building out a strong services division? How does Krish think about what makes for good margins in services businesses? How can one prevent themselves from being reliant on service revenue?
• Why does Krish believe that transparency is not always good when it comes to SaaS pricing? What are the cons of transparent pricing? Why does Krish believe if you are going to try freemium, it has to be from the beginning? How does Krish think about reinventing the wheel vs copying when it comes to pricing? How does Krish think about installing usage based pricing without disincentivizing usage? How can one do it?

Krish’s 60 Second SaaStr:

1. What does Krish know now that he wishes he had known at the beginning?
2. What moment in Krish’s life has served as an inflection point and changed the way he thinks?
3. What does Krish believe that most around him disbelieve?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: 

Jason Lemkin

Harry Stebbings

SaaStr

Krish Subramanian