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.

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

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

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

Karen Peacock is the COO @ Intercom, the company that provides a new and better way to acquire, engage and retain customers. To date, Intercom have raised over $240m in VC funding from some of the very best in VC including GV, Kleiner Perkins, Bessemer, ICONIQ and then individuals such as Mark Zuckerberg, John Collison, Biz Stone and Andy McLoughlin. As for Karen, prior to Intercom, she spent an incredible 17 years at Intuit leading all of Intuit’s small business products and services worldwide, a $2.2B business including QuickBooks, Accounting, Payments, and Payroll. As part of that, Karen managed a team of 500 and helped build one of the world’s largest SaaS businesses.

In Today’s Episode We Discuss:

• How Karen made her way into the world of SaaS with Intuit and how that led to becoming COO @ Intercom today? What were Karen’s biggest takeaways from her time at Intuit?
• What does Karen mean when she says “watch what customers do, not what they say”? How does Karen think about the difference between being customer driven vs customer informed? Why is it important to fall in love with the problem and not the solution as an entrepreneur?
• Karen has grown Intercom from 350 to 600 in 18 months, what would Karen’s biggest advice and learnings be when it comes to team assembly and hiring the best? What can one do to stress test the fit of the candidate pre-hire? What does Karen always find to be the most revealing questions to ask?
• When does Karen believe is the right time to hire a COO? How does one know when they have the right COO fit? What are some best practices for onboarding a new COO? What is the optimal relationship between CEO and COO?
• Karen has seen incredible scaling first hand both with Intercom and Intuit, what would some of her biggest takeaways and advice be on scaling? Where does Karen see many make mistakes in the scaling phases? What does Karen mean when she speaks about “the most important metric that you probably aren’t tracking?”

Karen’s 60 Second SaaStr:

1. What does Karen know now that she wishes she had known at the beginning?
2. What motto or quote does Karen frequently revert back to?
3. What is the most challenging element in Karen’s role 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

Karen Peacock

Hannah Willson is the VP of Sales @ Rainforest QA, the on-demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest have raised over $40m in funding from some of the very best in SaaS including the legendary Byron Deeter @ Bessemer, Jason Lemkin @ SaaStr, Marc Benioff himself, Andreesen Horowitz and YC. As for Hannah, she has over 10 years of experience leading sales and customer teams at both startups and publicly traded companies including seeing the first hand hyper-growth of Zenefits in their heyday and being VP of BD, Sales and Customer Renewals for the western half of the US at HelloWallet, prior to their acquisition by Morningstar.

In Today’s Episode We Discuss:

• How Hannah made her way into the world of SaaS and enterprise sales, came to join Zenefits in their heyday and how that led to her move to VP of Sales @ Rainforest?
• How does Hannah think about time allocation and prioritisation of time across leads and the sales pipeline? WHat can AEs do in terms of optimising their win rate of opportunities? How important a role should discounting play in winning potential leads? Does Hannah optimise for quality or quantity of logos in the early days?
• What does Hannah mean when she says the secret to success is “the calls between the calls”? How do these vary both in content and tone to traditional sales calls? Why must AEs be willing to open up and be vulnerable with leads? What can managers do to engender this? What is the optimal relationship for AEs and product team?
• What does Hannah believe is the right mechanism for feedback delivery? What has worked well for her in the past? Where does Hannah see many today going wrong? What guidelines need to be put in place to ensure this candid and transparent feedback is effective?

Hannah’s 60 Second SaaStr:

1. What does Hannah know now that she wishes she had known at the beginning?
2. What does Hannah believe embodies good sales rep productivity?
3. What is Hannah’s fave SaaS reading material?

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

Kyle Porter is the Founder & CEO @ Salesloft, the leading sales engagement platform delivering a better sales experience. To date, Salesloft have raised over $75m in funding from some of the best in the business including Emergence, Insight Venture Partners, Techstars and even LinkedIn. As for Kyle, he has led the team from 4 employees in 2014 to over 320 today where they have also been awarded Atlanta’s No 1 best place to work. Prior to founding Salesloft, Kyle was the Founder @ B2B camp, a conference focused on B2B revenue generating professionals. Before that he was Vice President of Marketing @ NanoLumens.

In Today’s Episode We Discuss:

• How Kyle made his way into the world of SaaS and came to found Salesloft?
• Kyle made the decision to pivot the product when it was at $7m in ARR, what was the thinking behind that? How does Kyle think about pivots more broadly? How does one know when it is truly not working? How long did it take Kyle to get the core Salesloft product to $1m in ARR?
• With the pivot, what were Kyle’s core learnings on migrating from a prior product and platform to a new one? What were his big lessons on seeing the change in buyer persona? What does Kyle mean when he says “selling is hard but buying is even harder”?
• Does Kyle agree with many CEO’s the most important role of the CEO is “management upscaling”? What elements does he find most challenging? What have been Kyle’s big lessons in the building out of his exec team? What is the fundamental element for a successful exec team to function?
• Salesloft is in an immensely competitive space, what would Kyle’s advice be in standing out in an intensely competitive space? Where do many go wrong? What are the pros and cons of being in Atlanta and not SF? What advice would Kyle give to founders operating their HQs external to the core hubs?

Kyle’s 60 Second SaaStr

Is it important to have early champions? How does one get them?

How has having kids changed your perspective on work?

Tell me a moment in your life that has served as an inflection point and changed the way you think?

When I say success in SaaS who is the embodiment of this to you?

What does Kyle know now that he wishes he had known at the beginning? 

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
Kyle Porter

Craig Walker is the Founder & CEO @ Dialpad, the startup that provides a business phone system for the modern workplace. To date, Craig has raised over $120m in VC funding with Dialpad from some of the best in the business including Iconiq, Andreesen Horowitz, Google Ventures, Felicis and Bill Marris’s Section 32. Prior to Dialpad, Craig was an EiR @ Google Ventures and founded and product managed Google Voice. Before that Craig founded Grand Central Communications, a personal communications startup that was acquired by Google. Finally prior to that, Craig enjoyed roles in the world of VC as General Partner @ Sterling Payot Capital and Founder & Senior Director of Yahoo Voice.

In Today’s Episode You Will Learn:

• How Craig made his way into the world of SaaS following time as both a GP in the world of venture and then as the creator of what would become Google Voice?
• Why does Craig think go-to-market is the most challenging element of being a CEO? How does Craig think about when is the right time to go large on go-to-market? Where does Craig believe most founders make mistakes here?
• How does Craig look to balance aggressive scaling of team with the maintaining of early company culture? What are the foundations to doing this successfully? How does Craig approach the element of hiring external talent vs promotion from within? How does Craig think about managing the internal discontent if hiring an external candidate?  
• How does Craig assess the effectiveness of trials in attracting large enterprises? What are the parameters that must be set for a trial, before it is agreed? What must founders learn to say no to when it comes to trials? How does Craig approach discounting? Why does Craig argue if your client asks for aggressive discounts, you have not explained your core USPs successfully?    

Craig’s 60 Second SaaStr

1. What does Craig knows now that he wishes he had known at the beginning?
2. When I say success in SaaS, who does Craig first think to and why?
3. Quality or quantity of logos 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

Craig Walker

Christoph Janz is the Managing Partner @ Point Nine Capital, one of Europe’s leading early stage funds with a portfolio that includes the likes of ZenDesk, Algolia, Delivery Hero, Revolut, Contentful and many more incredible companies. Before that, he co-founded two Internet startups (DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio, FreeAgent – and his love for SaaS. Christoph is also the writer of the phenomenal blog, The Angel VC, a must read for me.

In Today’s Episode You Will Learn:

• How Christoph made his way from serial founder to angel in ZenDesk to today, founding one of Europe’s most successful early stage funds in the form of Point Nine Capital?
• Product market fit is one of the most used words in the industry, so wtf really is product market fit? What does product market fit look like in terms of metrics across the core disciplines: MRR, churn and conversion from free to paid?  
• What is the hailed question that all Series A and B investors want to know? What does it take to make the graduation from Seed to Series A today? In terms of scaling, why does pouring fuel on the marketing fire not always equal more leads? How does Christoph view the role of outbound? Why is it such high hanging fruit? What is core to executing outbound successfully?
• Point Nine did a comprehensive assessment of how founders view the fundraising process, what were the biggest elements founders dislike about the process? From now on, what is the thinking behind the strategy that Point Nine will always do their pro-rata in the Series A? How does this affect reserve allocation?  

Christoph’s 60 Second SaaStr

1. What does Christoph know now that he wishes he had known in the beginning?
2. What does it take for European founders to make it big in the US?
3. Most common mistakes CEOs make in the scaling process?

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

Christoph Janz

Tom Bogan is the CEO of Adaptive Insights, the company that proves a new generation of business planning software for finance and beyond. Prior to their reported $1.55Bn acquisition to WorkDay, Adaptive Insights raised over $175m in VC funding from the likes of Bessemer, Salesforce Ventures, Norwest Venture Partners and many more incredible investors. Prior to Adaptive Insights, Tom was a partner at Greylock Partners where he focused on enterprise software investments. He was also president and COO at Rational Software until its acquisition by IBM. Before Rational, Tom served as CEO at Avatar Technologies and Pacific Data. He began his career as a financial officer in both public and private companies, serving as CFO at SQA and Orange Nassau, Inc., as well as vice president of finance at SCA Services.

In Today’s Episode You Will Learn:

• How Tom made his way into the world of SaaS, came to be a Partner with Greylock and then made the move back into operations with Adaptive Insights?
• Elad Gil has previously said the role of CEO is to “find product market fit, ensure the company does not run out of money and ensure the team does not implode”, how does Tom define his role as CEO of a $100m+ SaaS company? How does the role of CEo fundamentally change over time? What aspect of the role does Tom find most challenging?  
• What core role of CEO is constant throughout the lifecycle of the company? From seeing many of the world’s best SaaS CEOs, what are the commonalities in how the very best CEOs hire the very best execs? How does Tom think about the debate of hiring externally or promoting from within? How does Tom look to reduce internal discontent when hiring externally rather than promoting?
• At $100m Jyoti Bansal said on the show, this stage is about “creating and sustaining operational efficiency”. What have been Tom’s biggest learnings on the creation and maintenance of operational efficiency? What has worked? What has not worked? How does Tom think about internal asset allocation?
• Why does Tom believe that ultimately, ARR growth is the metric to rule them all? How does Tom think about and prioritise the metric stack in SaaS? How does he approach payback period vs CAC/LTV? In terms of services components of businesses, does Tom believe these should be baked into the CAC? What should the financial targets be for these services businesses?  

Tom’s 60 Second SaaStr

1. What does Tom know now that he wishes he had known at the beginning?
2. Tom’s favourite business reading material and why?
3. What would Tom most like to change in 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

Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M)  and big data leader Aster Data (acquired by Teradata for $325M).

In Today’s Episode You Will Learn:

• Why does Dave believe it is foundational to be an ARR first company? How does Dave think startups can show their ARR first mentality from the first investor meeting? How does this help drive operational efficiency? How does Dave segment ARR into 3 distinct camps?
• Why does Dave argue that SaaS metrics are not nearly as simple as they seem? Which metrics does Dave believe most founders confuse? What metrics will the best VCs pick apart and dig deep on? How can founders respond with accuracy and confidence?
• How does Dave respond to multi-year deals? Under what conditions are they acceptable and not acceptable? How must they be reported in accounting? Where do many startups go wrong when considering multi-year deals? How important is it for them to be pre-paid?
• Why does Dave argue that renewals do not measure customer satisfaction?What is an accurate measurement to determine customer satisfaction? How often should this be conducted? What sample size of customer gives the right amount of data?  
• How does Dave approach comp with regards to sales team cross-sell and upsell? Why is it not as black and white as boards often portray? Under which circumstances does Dave believe double comp is justified and not justified? How can you communicate this to your board successfully?

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

Dave Kellogg

If you’re looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr.

Timo Rein is the Founder & CEO @ Pipedrive, the startup that helps sales people focus on actions that close deals. To date, Timo has raised over $30m from the likes of Atomico, Bessemer Venture Partners, TransferWise Founder Taavet Hinrikus and Andy MCloughlin and has scaled the team to over 330 people across multiple continents. Prior to founding Pipedrive, Timo was a Partner @ Vain & Partners acting in a consultancy role on how to get the best ROI from your sales process and before that was himself a door-to-door salesman with SouthWestern Company selling high ACV products.

In Today’s Episode You Will Learn:

• How Timo made his way into the world of SMB CRM with the founding of Pipedrive from the days of being a door-to-door salesman of high ACV products?
• Why did Timo choose to go global with Pipedrive from day 1? What are the benefits of founders having this global mindset from the start? What are Timo’s biggest learnings in terms of acquiring customers globally early on? What worked? What did not work? How did Timo think about pricing on an individual country perspective? What are the challenges with this?
• Having raised from both US and UK VCs, how does fundraising differ when comparing Europe to the US? If Timo had to say the West Coast, East Coast and European VCs each had one area they focus, what would that area be? What are the challenges with these inherent focus points? What advice would Timo have for foreign founders looking to make it big in the US?
• How does Timo look to manage a team so spread across the globe? What are the core challenges of this? What works? What does not work? What functions can be split up by geography? What must remain in one location? Now at 300 people, how does Pipedrive ensure for the same values fit when hiring at scale?
• Many VCs say with such low ACV and such high churn, the SMB market is too difficult. How does Timo respond to this? How does Timo think about ensuring the continuous refilling of top of funnel? How does Timo think about acquiring such small customers in a cost efficient manner?    

60 Second SaaStr?

1. What does Pipedrive look like at $100m ARR?
2. What keeps Timo up at night?
3. Who is Timo’s favourite angel investor?
4. What does Timo know now that he wishes he had known at the beginning?

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

Timo Rein

Clate Mask is the CEO of Infusionsoft, the leading cloud-based CRM platform for growth-minded small businesses with more than 145,000 users worldwide. Under Clate’s leadership, InfusionSoft has grown from a fledgling startup housed in a worn-down strip mall into a 550 person company, raising over $130m in VC funding in the process. If that was not enough, Clate is also an angel investor with the likes of CampusLogic, where he also sits on the board and is co-author of Conquer the Chaos: How to Grow a Successful Small Business Without Going Crazy.  

In Today’s Episode You Will Learn:

• How Clate made his way into the world of SaaS and came to found the leading CRM for small businesses?
• Enterprise vs SMB: Why does Clate fundamentally believe that not everyone has to move to enterprise with time? Why do so many founders believe they need to? Why is it such a preference for investors? How does the decision to remain in SMB change the future structure of the team and product roadmap? What was the hardest challenge for Clate about staying in SMB?
• The Metrics Stack: What is the core metric that founders must observe to analyse the state of their business? How does this core metric affect every other metric? How does Clate view the significance of payback period, what is good to him? How does sales rep productivity change when serving SMB vs enterprise? What is good sales rep productivity? Why does Clate fundamentally believe CAC/LTV is the mothership? What is it solely driven by?
• Partnerships 101: How can a founder know whether they have the right model and product for a partnerships model? How do partnership models change both the service and sales process of your company? What are the biggest risks to implementing a full-scale partnerships model? What have been the biggest challenges for Clate of scaling this partnerships model?

60 Second SaaStr

1. What does Clate know now that he wishes he had known at the beginning?
2. What is the most important element an investor can provide?
3. A moment in Clate’s life that has changed the way he thinks and sees the world?

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

Clate Mask

Mark Mader is the CEO @ Smartsheet, the company that allows firms the best way to plan, track, automate and report on work. To date, they have raised over $105m in funding from some of the best in the business including Insight Venture Partners. Prior to Smartsheet, Mark served as senior vice president of global services for Onyx Software, leading the consulting and customer operations teams in the Americas, Europe, and Asia. Due to this success, in 2015, he was recognized as Ernst & Young Entrepreneur of the Year in Technology for the Pacific Northwest.

In Today’s Episode You Will Learn:

• Why Mark’s being disrupted by Salesforce led to his entry into the world of SaaS and how he came to be CEO @ Smartsheet?
• How does Mark think that startups should approach hiring across market cycles? What have been some core lessons Mark has learnt in frothy markets and the war to win “hot talent”? How does Mark think about “paying up” for certain candidates? How flexible should startup founders be on moving their compensation bands?  
• Why does Mark believe that too many people over index culture fit? How does Mark look to balance between raw IQ and culture fit? How does Mark look to really stress test someone’s ability to perform a role, pre-hire? Where do most startups go wrong in their early hiring processes?
• How does Mark think about creating a structured framework for giving employee feedback? Why do people overestimate the importance of the feedback itself? What else should they be focusing on?
• In terms of providing that feedback, how does Mark assess the importance of output? How does Mark look to balance the complicated elements of output vs input? Is it really all about activity?

60 Second SaaStr

1. What does Mark know now that he wishes he had known at the beginning?
2. Management upscaling is the most important role of CEO?
3. When is a stretch VP a stretch too far?

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

Mark Mader

Des Traynor is the Co-Founder, Chief Strategy Officer and VP of Marketing at Intercom, one of the world’s hottest startups that simply put, makes communicating with customers easy and efficient. They have raised over $115m in funding from some of the world’s leading investors including Social Capital, Index Ventures, Bessemer Venture Partners and then titans of industry with Mark Zuckerberg, Jack Dorsey and the Collison brothers at Stripe. Prior to Intercom, Des previously co-founded Exceptional (now a part of Rackspace), and prior was a UX designer for web applications.

In Today’s Episode You Will Learn:

• How Des made his way from founding consultancy web design businesses in Ireland to founding SaaS superstar, Intercom, with Eoghan and moving to San Francisco?
• Why does Des believe that “brand is the most overlooked element for new startups”? How must founders think differently when constructing their brand for a single product vs multi-product company? What is the right way to think about this brand architecture?
• How involved should customers be in the development of product roadmap? Where are the nuances and challenges to this? When is the right time to start thinking about releasing a second product? What is the right and the wrong way for this to be marketed?
• What does Des mean when he says, “there is an inverse correlation between quality and market size”? How should founders think about selling to both SMB and enterprise? How do their buying psychology and implementation process differ?

60 Second SaaStr

1. When I say success, who is the first person that comes to Des’ mind?
2. Where do most startups go wrong with their branding?
3. What does Des know now that he wishes he had known at the beginning?

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

Des Traynor

Greg Schott is the Chairman and CEO @ Mulesoft, provider of the leading platform for building application networks. They have raised over $250m in funding from some of the best investors in the world including NEA and Lightspeed and then some of the largest companies of the day in Cisco, Salesforce and SAP. Greg joined Mulesoft in 2009 when the company only had 20 employees, over the last 8 years Greg has scaled the team to over 1,000 today in 18 countries. A real software industry veteran with over 20 years of experience building and leading high growth technology companies from early stage through IPO.

In Today’s Episode You Will Learn:

• How Greg made his way into the world of SaaS and came to be CEO @ Mulesoft?
• Greg has seen Mulesoft scale from 20 to 1,000 employees today, what have been the biggest challenges in scaling the team? Where are the breaking points? What are the signs of those impending breaking points? How does that show through the team behaviour?
• Where do most companies go wrong in the hiring process? What is the right and wrong way to respond when a bad hire has been made? How long is long enough to determine whether a bad hire is a bad hire? Does Greg agree with the hire fast, fire fast thesis?
• If Greg could go back to 2009 when he joined the firm with 20 employees, what would Greg change about the way he approached hiring? What hiring advice would Greg give to an early stage SaaS company?   
• How does Greg think about scaling sales teams? How does Greg view specialisation in the scaling of sales? When is the right time? What should CEO’s look for in their sales leaders? How does that alter at different points in the journey?

60 Second SaaStr

1. How have things changed since IPO?
2. When is the right time to expand product line and enter new segments?
3. Biggest challenge with Mulesoft today?
4. Which SaaS CEO does Greg most admire and why?

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

Greg Schott