Matt MacInnis is the Founder & CEO @ Inkling, the company that brings policies and procedures to life for your desktop workers. The company has backing from some of the best investors in the world with the likes of Sequoia, Felicis and Kapor Capital behind them. As for Matt, prior to Inkling, he spent 7 years at the one and only Apple Inc. I would also like to say a huge thank you to Taro Fukuyama, Founder @ AnyPerk for the intro to Matt.

In Today’s Episode You Will Learn:

• How did Matt make his way into the world of SaaS and Inkling from Apple Inc?
• Does culture in sales really matter? Is it not just about hitting the fucking number? What are the two opposing culture that exist in the world of sales team? Why is missionary always better?
• How can a sales leader instill a competitive element into a missionary sales culture? What are the inherent challenges and how does Matt approach them?
• Is it possible to have a fantastic sales and a fantastic engineering culture? How can the two live under the same roof and what needs to happen to ensure this works?
• In terms of measurement, how can a founder know whether they have a strong culture? What are the signs and indications?

60 Second SaaStr

1. Productivity Tools
2. What does Matt know now that he wishes he had known in the beginning?
3. Biggest mistake most SaaS companies are enacting with their sales process?

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

Matt MacInnis

Whitney Sales is the VP of Sales at TalentIQ, has been involved in bringing products to market and managing high growth sales teams for over a decade. She is the creator of the Sales Method, a strategic framework for launching products, which she used to help three companies earn a place on the Inc 5000 fastest growing companies list. Prior to joining TalentIQ, Whitney held executive positions at Wanelo and SpringAhead and currently serves as a mentor at StartX, Alchemist, and previous guest Acceleprise and a huge thanks to Michael Cardamone @ Acceleprise for the intro to Whitney today.

In Today’s Episode You Will Learn:

• How did Whitney make her way into the world of SaaS and more specifically sales?
• What are the 5 key criteria that founders need to consider before embarking on the sales process?
• How specific and targeted should a customer profile be? How many profiles can they have? What are the best questions to determine the optimal customer segment?
• How can founders identify which buyers are innovators? What tools are best for this? Once discovered, how should founders approach these innovators?
• Founders learn about gaps in customer information from selling. So how close should the integration of content marketing and selling be in the early days?

60 Second SaaStr

1. What are Whitney’s preferred tools for her tech stack?
2. What does Whitney know now that she wishes she had known at the beginning?
3. Does the proliferation of sales tools make it harder or easier?

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

Whitney Sales

Ryan Petersen is the Founder and CEO of Flexport, the freight forwarder for the internet age. Flexport recently raised a phenomenal $65m Series B from the likes of Founders Fund, First Round, Felicis, Bloomberg Beta, Yuri Milner, Susa Ventures and more incredible investors. With none other than YC founder Paul Graham stating ‘Ryan has the rare ability to not just satisfy the market but grow it’. Prior to Flexport, Ryan was Founder and CEO of ImportGenius.com, the largest provider of business intelligence to the import-export industry. A huge hand to Chad Byers @ Susa and Jason Lemkin for the intro

In Today’s Episode You Will Learn:

• How did Ryan make her way into the world of SaaS and come to found Flexport?
• How does Ryan view NPS? Why is he so bullish? Why is it the most important metric? What are the downsides to relying on NPS?
• What is the optimal method to structure internal compensation structures? Why is compensation based on NPS and Net not effective and what are the dangers of this?
• How can founders look to implement bottoms up decision making in their organisation? What are the benefits of this and what are the challenges to it’s implementation?
• Ryan is hiring his first VP of Marketing? What should founders look for in their VP of Marketing? Why is now the right time and what challenges has Ryan faced in the process?

60 Second SaaStr

1. Fave SaaS reading material?
2. What does Ryan know now that he wishes he had known when he started?
3. What has been his biggest learning throughout the Flexport journey?

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

Ryan Petersen

Josh Reeves is the Founder and CEO @ Gusto. Gusto reimagines payroll, benefits, HR, and personal finance and it is this reimagination that has led to their recent addition to the unicorn club with investors including Google Capital, Kleiner Perkins, Data Collective and General Catalyst, just to name a few. As for Josh, he was selected for the 2012 Forbes 30 Under 30 list. Prior to co-founding Gusto, he was the CEO and co-founder of Unwrap, a SaaS startup which was acquired in 2010, and he began his career as an early employee at Zazzle. I would also like to give a big hand to Jason Lemkin and Phil Libin for the intro to Josh today.

In Today’s Episode You Will Learn:

• HR and Payroll is not sexy so how did Josh make his way into the industry and what was the a-ha moment for Gusto?
• Josh has said before ‘he lives and breathes how a company is built.’ How has Josh looked to grow and develop his own internal organisation at Gusto? How does this vary with stage?
• Josh has hired over 300 people at Gusto, how does he approach the interview process? What is the right way for employers to approach the ‘making offers’ stage?
• How important does Josh feel it is to have an ownership culture and internal entrepreneurialism? How can this environment be fostered and developed?

60 Second SaaStr

1. How employers can ensure new employees have an amazing first day?
2. What does Josh know now that he wishes he had known when he started?
3. The biggest mistake SaaS companies make with their HR and payroll organisation?

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

Josh Reeves

Jeff Fernandez is the Co-Founder & CEO @ Grovo, the enterprise learning solution that allows you to educate and empower your employees. At Grovo, Jeff oversees sales, investor relations, and the building of Grovo’s award-winning culture. Prior to founding Grovo in 2010, Jeff served as product manager at Clickable (acquired by Syncapse). From 2006 until 2009, he led business development and sales for Doostang (acquired by Universum Global), an online career networking community. Jeff is also a bit of a rockstar off the field getting the highest honours from Harvard penning his thesis on human performance and then playing semi pro football for the New York Rebels in 2008. I would also like to say a massive thank you to Greg Sands @ Costanoa Venture Capital for the intro to Jeff today.

In Today’s Episode You Will Learn:

• How Jeff came to found Grovo? What was the a-ha moment for him?
• Jeff is renowned to ‘lead from the heart’. What are the advantages of this as a CEO? How does this affect the company, the culture? What are the inherent challenges?
• Question from Greg Sands: Jeff likes to ‘work the sales floor’, how does that work? What does Jeff actually do? What have been Jeff’s observations having seen the sales floor up close?
• How does Jeff look to structure the compensation for his sales team? How does this vary with time and stage?
• What does Jeff mean when he says ‘sometimes you have to go slow to go fast’? How does that play out in his management style?

60 Second SaaStr

1. Jeff’s biggest productivity tips?
2. Biggest challenge for Jeff in being CEO @ Grovo?
3. What does Jeff 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

Jeff Fernandez

Sangram Vajre is the Co-Founder & CMO at Terminus, the leading account-based marketing platform. Prior to Terminus, Sangram was the Head of Marketing @ Pardo, prior to it’s acquisition by Salesforce. Sangram is also the brains behind the marvel that is Flip My Funnel which challenges the status quo of traditional B2B marketing practices and transform how B2B marketers approached driving revenue in their organization. You might remember in a recent episode Tim Kopp @ Hyde Park Ventures cited Sangram and his revolutionary approach with Flip My Funnel as one to watch. If that was not enough, Sangram is also the author of "Account-Based Marketing For Dummies".

In Today’s Episode You Will Learn:

• How Sangram came to found Flip My Funnel and Terminus? What was the a-ha moment and origin story for Sangram?
• Why does Sangram believe the funnel needs to be reinvented? Where are the inefficiencies? What can be done to optimise the funnel and what are the steps to do so?
• How did Sangram establish such a strong brand in the B2B space on a shoe-string budget in such a short space of time? What tactics can be done to exert your authority over a domain?
• How does Sangram look to create an ownership culture of internal entrepreneurs at Terminus? Why is it so important to try and hire people who know more than you?
• Why did Sangram decide to hire a customer success rep before any other function? What did he look for in his first CS person? What does Sangram thinks is fundamental to being successful at CS?

60 Second SaaStr

1. Biggest learning from founding and scaling Terminus?
2. Sangram’s Favourite SaaS reading material?

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

Sangram Vajre

Matt Murphy is a Managing Director @ Menlo Ventures where he focuses on multi-stage investments across cloud infrastructure and AI-first SaaS applications. Since joining Menlo, Matt has led investments in Heap Analytics, Usermind, and Veriflow. Previously, Matt was a General Partner at Kleiner Perkins for over 15 years.  Matt was also an observer at Google (from initial investment to IPO), launched the iFund in ’08 (a collaborative initiative with Apple to build the defining applications on the iOS platform), and led KPCB’s investments in AutoNavi (Nasdaq: AMAP, 2010) and Aerohive Networks (Nasdaq: HIVE, 2014). Before joining KPCB, Matt worked at semiconductor startup Netboost (acquired by Intel) and prior to that at Sun Microsystems.

In Today’s Episode You Will Learn:

• How Matt made his way into the world of VC and enterprise investing? What were his biggest takeaways from working alongside John Doerr @ Kleiner Perkins?
• How is the enterprise investing landscape changing? What fundamental shifts have we seen and what have been the dominant repercussions of this?
• Nakul Mandan stated that ‘we would see the 2nd wave of consumerisation of enterprise through business model’. Does Matt agree with this and what key trends is Matt most excited about in SaaS?
• How does Matt look to evaluate early stage SaaS valuations? What are people fundamentally misvaluing and how should the topic be approached?
• Is it harder now for SaaS companies to raise than ever before? What metrics does Matt look for in a Series A investment opportunity?  

60 Second SaaStr

1. Matt's Fave SaaS reading material?
2. What are the greenfield opportunities in SaaS today?
3. What was Matt's biggest takeaway from working with John Doerr @ Kleiner Perkins?

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

Matt Murphy

Brandon Bruce is the Co-Founder and COO @ Cirrus Insight, the plugin for Gmail and Outlook that automatically updates Salesforce as you work. Cirrus is a bootstrapped startup with triple-digit yearly growth since it's founding 4 years ago and has grown from 2 co-founders in 2011 to a team of 55 people today. And I have to say a huge thanks to Aaron Ross, Author @ Predictable Revenue for the intro to Brandon today. Likewise, if you want to join me and Jason for mojitos at SaaStr Annual 2017 and also want an incredible 20% off ticket prices, then all you have to do is click here!

In Today’s Episode You Will Learn:

• How did Brandon make his way into the world of SaaS and come to found Cirrus Insight?
• What does Brandon mean he says he likes to take the road less travelled in Sales? What have been his learnings from his interactions on the front line of sales? How has it changed how he approaches sales?
• How are Cirrus so efficient at events in terms of getting more leads, meeting and sales? What is the strategy going into events? How can we optimise this?
• Speaking of events in general there, how does Brandon look to define prospect and buyer personas? How important is this for events? How narrow and specific do these personas have to be?
• Brandon has stated before in the importance of learning and doing manual before automatic with the future in mind. What do he mean by this and how does it affect his roadmap and thought process to the future going forward?

60 Second SaaStr

1. Favourite SaaS reading material?
2. What does Brandon know now that he wish he had known at the beginning?
3. The biggest challenge of running Cirrus and how Brandon looks to combat it?

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

Brandon Bruce

John Barrows is essentially the Godfather of Sales. We often have VPs of Sales from tech titans on the show but who trains those VPs and sales reps to be the best in the world at sales? That is where John Barrows comes in, with clients including Dropbox, Box, Marketo, Twilio and many more, John has amassed a wealth of knowledge and experience allowing him to provide the most proactive sales tips and strategies to optimise the sales process. If you have not checked out his blog, that really is a must and can be found here.

In Today’s Episode You Will Learn:

• How did John make his way into the world of SaaS and more specifically sales optimisation?
• How has John seen the sales landscape evolve? What has been the effect of the segmentation of roles pioneered by Salesforce?
• What will be the catalyst that causes teams to shift from current sales methods and teams to AI replacing the sales team? What does this depend on?
• How does John view the integration of sales and marketing? How does the rise of ABM change this?
• How can sales reps perfect the balance of being direct and being rude? How important is a summary email? What is the optimal structure and how should sales reps follow up on summary emails?

60 Second SaaStr

1. The most common question asked to John by VPs of Sales?
2. What are the benefits of Top Down prospecting?
3. Do execs need structure?

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

John Barrows