Whitney Bouck (HelloSign): Sales Collider meetup

Whitney Bouck, COO at HelloSign

I attended my second Sales Collider meetup this afternoon near Union Square in San Francisco. Sales Collider Founder Ryan Williams and his team did an excellent job keeping the event founder friendly, on time, and packed with relevant, timely content for SaaS founders like myself.

Earlier today, Ryan and Greg Afong did a deep dive with us at our office in SOMA. As we chart our next revenue milestone, a big piece of the puzzle will be building out our Outbound sales team and playbook. Mahalo R Dub and Afong! This evening's first speaker was Whitney Bouck, COO of HelloSign.

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Whitney Bouck - HelloSign COO

Here are my takeaways from Whitney Bouck's presentation:

• Joined HelloSign as Chief Operating Officer when they were at 40 employees.
• Has been a part of 3 IPOs.
• Previously employee #100 at Box.
• An important internal exercise: "What do you want your sales team to look like a year from now?”
• When planning, consider doing a pre-mortem: What are the things that could go wrong?
• Have Sales and Marketing teams physically sit next to each other. Have total alignment.
• Be thoughtful about your go-to-market (GTM) strategy.
• Re: comp plans: Have your reps know what kind of money they’re gonna make in a deal at any given day of the month. In other words, make it simple.
• “Annual contracts are *amazing* for cash flow.” (I could not agree more)
• “Do not cap commissions, people!”
• Regardless whether it's a simple or complex software solution, enterprise companies don't buy differently.
• Trust and security must be strongly emphasized in messaging for enterprise customers.

HelloSign

HelloSign is a a cloud-based electronic signature tool that enables users to sign, fill out, send, retrieve, and save documents paperlessly. Like many successful SaaS companies, they are about a mile from our office in San Francisco's SOMA district.