Sales and Marketing Strategies with Whitney Bouck, COO of HelloSign

If there’s anyone in the world who can teach you how to develop a sales and marketing strategy that drives growth, it’s Whitney Bouck. 

As the former SVP of Box Inc’s Global Marketing division, as well as the General Manager of their Enterprise division, she was responsible for changing the public perception that Box’s products were only for small businesses. She built their enterprise team from the ground up, hiring the division’s first sales and marketing reps before reshaping their strategy to drive growth on a global level. 

These days, Whitney is busy as both an advisor and as the COO of HelloSign, where she’s leading the company’s go-to-market efforts across multiple departments.

Whitney has been kind enough to join us at a few SalesCollider MeetUps, sharing some unbelievably valuable sales and marketing advice with our founders. 

A few highlights from her most recent presentation, How to Think Marketing and Do Sales , are available below. She also shared a few interesting lessons that she’s learned from working in enterprise sales, which we outlined underneath. 

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Some Thoughts on Enterprise Sales

Here are some lessons and takeaways Whitney has learned from living and breathing enterprise sales:

Building Traction is Long and Slow

Whitney says that this might seem obvious, but it’s a crucial thing to understand if you want to build a repeatable revenue process.

“Getting big companies to make decisions in any sizable fashion is hard because they don’t move quickly,” she explains, “They might be willing to experiment with a very small pilot but getting them into any sort of sizable deal is really difficult. You have to give it patience.”

Sales Cycles are Long (No Matter How Simple Your Product Is)

When she joined Box, Whitney assumed that, because their product’s use-case is relatively self-explanatory, the sales cycle would be much shorter than that of a company with more complex products. As she points out, however, the product doesn’t matter when it comes to enterprise sales cycles. 

“You have to realize that the people they have to involve to get buy-in on any sizable deal is the same whether their buying SaaS, end-user, infrastructure, cloud, whatever,” she says, “so their average sales cycle is always the same, six to nine months.”

You Need a Champion with Influence

Remember, there are a lot of job titles that have buy-in power in any given enterprise deal. Because of this, it helps to understand the inner workings of your target companies.

Whitney’s suggested: find people who work a the companies you want to sell to and learn as much as you can from them. “You have to have someone who’s going to give you the inside scoop,” she says, “someone who’s going to know who the decision makers are, who the naysayers are and who you need to win over."