At the tail end of June, we attended the SaaStr Summer Social in San Francisco at the SaaStr Co-Selling Space. It was a packed house with over 500 SaaS founders, investors and execs in attendance. Here are highlights from the sessions to apply to your SaaS business. 

(Note – I’ve paraphrased these quotes.)

“How to Really Hire a Great VP of Sales: 2017 Edition” with Brendon Cassidy (Cassidy Ventures) + Jennifer Lawrence (Duo Security)

You want to be at $8 – $10 million ARR before hiring your VP of Sales. But finding that amazing VP of Sales to take your SaaS business to the stratosphere is no picnic. Especially when there’s only 30 in the world that have scaled $50 million…

How to Build the List

“First, get a coach or three. You have your board and investors, but you need specific coaches. You aren’t supposed to know what you’re doing. Recruit 2-3 advisors or consultants with some sort of stake in company.

Ask your coaches, ‘if you were making this hire, who would it be? Top 3 choices?’ Great VPs of Sales and CROs foster admiration in their peer group. Ask founders and friends their top 3-5 choices. If the same names come up, they should be on the top of your list. Always try to engage with the top candidates because you never know. Look for in-house solutions. Look long and hard at internal folks before going for an external stretch or potential non-fit.” –Brendon

“When you are in startup growth mode, you need someone who knows how to roll up their sleeves and figure things out – not execute a playbook that was created for them.” – Jennifer

How to Select the Best Candidate

“Be able to check the boxes:

  • Does this candidate support the next 2 stages of company growth?
  • Are they comfortable running deals and hiring reps to support your current sales cycle?
  • Do they have a list of reps they would hire? Ask for and audit that list to ensure fit.
  • What type of leader are they?

If you get your ‘A’ you gotta pay. Be prepared. Passion about equity is a good sign they care about your company vs. someone who is more focused on their base salary.” – Brendon

“What should matter in your hiring decision:

  • Track record and past success – have they accomplished the multiplier you want?
  • Collaborative – they should interview you as well. At some point you are going to miss the mark. Do you want finger pointing between Sales and Marketing? Leads are like dripping ice cream cones. Get to them fast. You need teams to work together.
  • Creates a culture of success – optimizes for team
  • Servant leadership – they choose to invest in the team vs themself
  • Keep the bar high – don’t lower your standards when hiring. The only interview that really matters is the back channel. A solid recruiting team knows how to get that info.” – Jennifer

Jennifer Lawrence of Duo Security

Advice for Other Women in Technology Who Want to be Leaders

“For women out there thinking you might want to become a leader:

  • Jump before you believe you are ready
  • Remember to say thank you
  • Assume positive intent
  • The most important people in an organization are doers – invest in them
  • Care about people around you – not just about hitting your numbers
  • Hit your numbers if you want to do big things (this will take care of itself if you do other pieces)
  • Always hustle” – Jennifer

“Why Big Companies Really Buy from Startups: Stories from Uber, Netflix and More” with Shobhana Ahluwalia (Uber), Mike Kail (Cybric) + Peter Mullen as Moderator

SaaS businesses are constantly seeking to break into the enterprise sale. But how can a startup compete?

“Become a trusted partner by doing your research. Don’t try to be overly clever by mailing me a remote controlled car without the remote. Or trick my EA to patch you into my line. Before you start, get intel to make the introduction warm.” – Mike

“I know that it is all the rage to have SDR campaigns. But no matter how many cold emails you send, it might not be right time. If I don’t answer by the 3rd time, I won’t answer you. I don’t even carry business cards so my contact information is very difficult to get. I leverage forums for new trends and product data and get input from my team after they attend conferences.” – Shobhana

How can you tell if a salesperson has done their homework?

“I put our stuff out there to find.” – Mike

“Don’t come in with a generalized pitch. What can you do you my company?” – Shobhana

To list or not to list pricing? And why won’t you talk budgets?

“Yes, have your pricing on your website. It helps to see if your product’s in the ballpark. We can’t be transparent on our budget. Rather, we determine if the product fully solves a need and then go from there.” – Shobhana

“Budgets are arbitrary. It’s based on the ROI and value.” – Mike

What are ways you can avoid the grueling legal contract review that demands unreasonable security requirements and IP ownership?

“You have to engage security early on to understand requirements and regulation issues.” – Mike

“There will be certain things that are non-negotiable. Start early and explain what you need.” – Shobhana

“Raise a Huge Round, Hitting Escape Velocity, and What Changes at Eight Figures in ARR” with Nicolas Dessaigne (Algolia) + Jennifer Tejada (PagerDuty)

The Background

“We constantly try and measure efficiency in how we scale and grow. Sometimes it’s back to the future… Some things that didn’t work 2 years ago, now work. There’s no secret solution for high-growth land and expand. The vast majority of 6 figure deals come from smaller deals. Beware of the strategic vendor list; that is a Finance Department’s way to wear you down.” – Jennifer

“We sell to small, medium and large companies, and their needs on how to connect are different. Customer Service is huge for Algolia. When you have 130 employees, you look at how you triage to support 3,000 customers. We don’t have support people, we have product people. Every developer does support, and customers love this direct connection.” – Nicolas:

“For us, everything starts with the product. It’s easy to use, so self-onboarding creates immediate value. We have a dedicated customer success team, with dedicated account managers for bigger accounts. We are trying to get engineering and support in conversations with customers but buyer personas are very different. Getting PagerDuty as an organization to know those personas is important. Mistakes happen, but maintaining transparency in how you handle mistakes is critical.” – Jennifer

How to Leverage the CEO to Close Deals

“We use executive dinners to seed a new market. We have our target account lists and leverage our networks to make connections. It’s not about talking about PagerDuty. We use these events to add value. Our win rate goes up when I am in the deal. Customers love talking to the CEO.” – Jennifer

Jennifer Tejada of PagerDuty and Jason Lemkin of SaaStr

Creating Culture and Respectful Conversations

“Your culture is defined by the lowest form of behavior you will accept. How do you deal with those areas when people say the wrong thing? You need to make people feel comfortable to talk, a safe place in culture. If you see something and stand by, you are part of it if you don’t say something. You need to be able to have a respectful conversation. I highly recommend reading Radical Candor. Keeping low performers around is demotivating for everyone.” – Jennifer

The Toughest Change as Your Company Scales 

“The cost of hiring and doing business was double in San Francisco vs. Paris. That was a huge economic shock.” – Nicolas

What do you need all this money for?

“I think this bubble is going to pop. There’s more capital than high quality companies. We were having a moment of momentum, so it was a good time to raise capital. It took about 3.5 weeks to complete the process. It was all about timing and quality of the business and quality of the market. Our 2017 plan was funded with existing cash. Investors knew we didn’t need it. Instead it gives us the safety net of a rainy day fund so we can invest in strategic areas like machine learning. It also takes the pressure out of the system to hire experienced people. Our leadership team is never in stasis. There’s always 2-3 roles in transition. We can also open new channels to market and take risks with global. We will not get all of these right. There will be failure and failure is expensive. With extra capital you can afford to take more measured risks.” – Jennifer


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