Ryan Williams is the Founder @ SalesCollider, the organisation that helps technical founders jumpstart sales. Ryan got his start as the first sales manager at Adroll where he grew the team from 3 to 32 reps in just 8 months, a team that was responsible for ARR growing from $4m to $58m in under 2 years. Ryan then became an advisor to the early team at InVision where he coached both CEO and sales reps to close the first dozen enterprise deals. Then his last stop before founding SalesCollider was as VP of Sales at LeadGenius where he grew enterprise sales by over 400% and added clients such as Ebay, IBM and Google, just to name a few. Ryan is also an Entrepreneur in Residence @ 500 Startups and a Mentor with First Round Capital.

In Today’s Episode You Will Learn:

• How Ryan made his way into the world of sales as first sales manager at Adroll and how that led to advising the CEO of InVision on gaining their first enterprise clients?
• 70% of VPs of Sales fail when they join early stage startups, why is this? How can founders know when is the right time to bring in their first VP of Sales? What can they do to maximise the chances of success when bringing them into the organisation?
• What is the right profile type for the first VP of Sales? What are the core foundations to assessing the strength of the VP in the interview, especially for engineering minded founders? What is the one question that Ryan loves to ask potential sales candidates? What answer does he look for?
• Does Ryan agree with a recent guest, “discounting is now table stakes”? Where do most early stage startups go wrong when thinking about discounts? What framework must startups utilise to analyse the right discount to offer? Why must they know the internal value they are providing to their customer in such a detailed way when discounting?

60 Second SaaStr

1. What does Ryan know now that he wishes he had known at the beginning?
2. SDR’s are the most important function in sales, agree or disagree?
3. Sales rep productivity, what is good and what is bad?

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 Williams

Pieterjan (PJ) Bouten is the Founder & CEO @ Showpad, the world’s leading sales enablement platform that allows for the creation of amazing buyer experiences. To date they have raised over $89m in VC funding from the likes of Insight Venture Partners, Dawn Capital and Hummingbird. As for PJ, Showpad is the second company he has founded. In 2010 he co-founded the mobile development agency, In The Pocket and still serves on its board. Prior to In The Pocket, Pieterjan held senior roles at Netlog and Accenture.

In Today’s Episode You Will Learn:

• How PJ made his way from the world of Accenture to founding the world’s leading sales enablement platform in Showpad?
• What was the most challenging element for PJ and Showpad in scaling from $1m-10m in ARR? How does the go-to-market change with this scaling? How does the team structure and composition alter? How does the branding and positioning change?
• PJ has said before that you must “reiterate value at every touchpoint”, what does he mean by this? How can one look to build a structure and framework to ensure one is effective with this? How  does one scale this when serving thousands of SMBs?
• What were PJs biggest lessons from their experiences of discounting? What advice would PJ give to founders on when and how much to discount? How does PJ think about the use of pilots and trials? How can one ensure optimal efficiency of conversion with both methods?

60 Second SaaStr

1. Does the role of CEO ever get easier?
2. What does PJ know now that he wishes he had known at the beginning?
3. What keeps PJ up at night?

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

Pieterjan Bouten

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

Harry Glaser is the Founder & CEO @ Periscope Data, the startup that allows you to transform your business with the fastest, most powerful analytics platform. To date, Periscope have raised over $34m in funding from some of the very best in the business including Bessemer, SV Angel, DFJ, Susa Ventures and Data Collective, just to name a few. With this funding they now serve over 975 customers including Adobe, Flexport, Tinder, NewRelic and more. Prior to founding Periscope, Harry was a Product Manager @ Google. Fun fact about Periscope, it was voted the best small company to work for in 2017.  

In Today’s Episode You Will Learn:

• How Harry made his way from being a PM at Google to convincing his co-founder Tom to leave his comfortable corporate job in Seattle to chase the startup dream in the valley?
• Diverse Teams: There a a lot of all white male teams in SaaS, what should they do to create a more diverse, well-rounded team? What is the first step? What is the framework for achieving this hiring ambition? What are the biggest challenges? Where does Harry see founders most often making mistakes in building diverse teams?
• Data Teams: Why does Harry believe that founding teams must have data professionals within them from Day 1? Why does Harry believe this makes those startups more successful? What are the fundamental benefits? How does this data-centricity change the decision-making of the organisation? What are the core challenges in scaling this data team?
• Moving Upmarket: Why does Harry believe that it is better to do SMB to enterprise than enterprise to SMB? How does the product fundamentally change when addressing the enterprise market? How does the structure of the team change with the move? How does the messaging of the company alter with the move to a more enterprise focus?

60 Second SaaStr

1. What does Harry know now that he wishes he had known at the beginning?
2. Harry recently tweeted “you don’t choose the kind of CEO you are”, what kind of CEO are you then?
3. A moment in Harry’s life that has served as an inflection point and changed the way he thinks?
4. What can a founder do today to instantly make a better workplace culture?

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

Harry Glaser