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

Brad Birnbaum is the Founder & CEO @ Kustomer, the first intelligent platform for customer experience that enables you to know everything about every customer. To date Brad has raised over $38m in funding for Kustomer from some of the very best in the SaaS business including Tomasz Tunguz @ Redpoint, Ed Sim @ Boldstart, Canaan Partners, Box Group and Social Leverage just to name a few. Previously he was the Co-founder of Assistly, which was acquired by Salesforce and became Desk.com. Prior to that, he was CTO for Talisma and Co‑founder & CTO of eShare Technologies. In addition, Brad was also the CTO @ Sean parker’s Airtime and VP of Engineering with Salesforce.

In Today’s Episode We Discuss:

• How Brad made his way into the world of customer experience and SaaS over 20 years ago?
• This is Brad’s 4th time at the roadshow, what does Brad believe are the core benefits of repeat entrepreneurship? How did his prior experience change his operating mentality with Kustomer? What has he done differently this time? What worked and he has kept the same?
• Brad has made the transition from CTO to CEO, how did he find this transition? What were some of the most challenging elements? What have been some of the biggest surprises? What advice would Brad have for other CTOs who have made or are thinking about making the transition?
• Brad initially served SMBs with Kustomer but now primarily focuses on mid-level, what would Brad’s biggest advice be when it comes to finding the right go-to-market strategy for you? How did their transition alter their approach to pricing, product, messaging and distribution? Where does Brad see many people go wrong on go-to-market?

Brad’s 60 Second SaaStr:

1. What does Brad know now that he wishes he had known at the beginning?
2. When is the right time to pour fuel on the company fire?
3. What would Brad most like to change in the world of SaaS?

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

Brad Birnbaum

Jon Stein is the Founder & CEO @ Betterment, the online financial advisor built for people who refuse to settle for average investing. To date, Jon has raised $275m in VC funding with Betterment from the likes of Bessemer Ventures Partners, Menlo Ventures, Kinnevik and Francisco Partners, just to name a few. Prior to founding Betterment, Jon spent 4 years as a consultant at First Manhattan Consulting Group where he really honed his experience in working with banks and brokers including revitalizing a bank in Australia with the launch of a best-in-market auto-finance offering, resulting in 50% lift to revenue. As a result of his phenomenal success with Betterment Jon has won many awards including Fortune’s 40 Under 40.

In Today’s Episode We Discuss:

• How Jon made his way into the world of startups and came to found democratize the world of investing with Betterment?
• When does Jon believe is that critical moment when the founding team must hire their first employee? What is the right strategy to build the candidate pipe for hiring those first employees? Where does Jon see many go wrong here? What 1-2 questions does Jon always find the most enlightening to ask in the interview?
• Once hired, what have been some of Jon’s biggest lessons in terms of optimising the onboarding experience and the first 60 days? How has their process changed over time? How does Jon determine when a stretch candidate is a stretch too far? If so, what does Jon believe is the right way to let go of an individual?
• What does Jon believe to be the 3 core roles of the CEO in any company today? From those, what has Jon found most challenging? What did he do to level up and overcome the challenges? How does Jon approach transparency with the team in delicate cases like fundraising and acquisition etc?
• With the team and product in place, scale can occur, what are the 2-3 things that all companies need to focus on when product market fit has been achieved? How does Jon determine when is the right time to really put the pedal to the metal and scale?

Jon’s 60 Second SaaStr:

1. Jon’s favourite book and why?
2. What does on know now that he wishes he had known at the beginning?
3. What is Jon’s biggest strength and weakness?

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

Jon Stein