Building an Effective GTM Strategy with Whitney Bouck

Whitney Bouck is the COO at HelloSign, the rapidly-growing eSignature platform. As the former Senior VP of Global Marketing and GM of Enterprise for Box Inc, she’s renowned for her expertise in sales and marketing strategy.


Photo: Hoala Greevy of  Paubox

Photo: Hoala Greevy of Paubox

We were very fortunate to have Whitney join SalesCollider for our most recent of our MeetUps, where she presented on some of the various lessons she’s learned about startups over her 25-year career. Her talk, entitled How to Think Marketing and Do Sales, touched on everything from building a first-time sales team to developing a compensation plan that promotes growth.

Throughout her talk, Whitney shared some stories that gave us a glimpse into the process of “going enterprise”. As the architect of Box’s initial enterprise team and the driver of their global marketing strategy, she played a key role in their transition from a consumer service to an enterprise giant. 

Her anecdotes and advice are extremely valuable for founders in any segment. Whether you’re striving to succeed in the enterprise space, selling directly to consumers, or anywhere on the spectrum in between, she’s been where you are and thrived there, too. 


Letting Your Buyer Determine Your Go-to-Market Strategy

If your go-to-market strategy isn’t catered to your buyer, you’re going to waste a lot of time and money trying to reach them. As Whitney says, “If you’re trying to sell to the Fortune 2000, then you’re going to have a totally different sales and marketing engagement model than you will if you’re selling to consumers, so be smart about that.”

Making smart choices, Whitney explains, means looking at how you can reach your customer in the most cost-effective manner possible. “If your target is selling to consumers, don’t hire a bunch of direct salespeople,” she says, “Think about leaning more toward self-service and freemium as your sales model. That way, everything’s online.”


  • Self-Service

  • Freemium


  • SDR's

  • Self-Service + Phone Sales


  • SDR's

  • Direct/Field Sales

  • Sales Engineers

If you’re targeting enterprise companies, however, you’ll need to allocate more funds toward reaching them. It’s unlikely, after all, that you’re going to get in touch with the CIO of a 5,000-employee company by adding them on LinkedIn. “Executives in very big companies aren’t going to open your emails, they’re not going to pick up the phone,” Whitney explains, “The only way you’ll get to those people is through high points of engagement, like events, which are often very expensive.”

Ultimately, these are your customer acquisition costs and need to be considered carefully. If you have a strong GTM, you’ll use these costs to determine goals, quotas and comp plans as you scale. 


Modeling Your Sales Numbers


Being a founder requires relentless optimism. As a result, they often project much higher close rates than they’re actually capable of achieving, particularly in the early stages. “You have to have big hopes, dreams, a whole lot of faith and maybe a little insanity,” she says, smiling, “The one place where you want to be a little conservative, especially if you’ve taken investment money, is in modeling your sales numbers.”

Realistic, data-driven goals will prevent you from hiring employees that you’ll have to lay off after a bad quarter. They’ll also give you and your team achievable milestones to strive for. “Round down a little bit until you have enough data to really know [the sales you’re capable of achieving],” she suggests, “It’s important to have something that you’re shooting for, that you’re trying to motivate other people around you to hit.”

Rounding down, she says, is a way to account for the fact that you and any reps you have may not be able to meet quota every quarter. Along with this, she advises founders to do a “pre-mortem” before each deal, just as we are accustomed to doing postmortems after each deal. This enables the founder to predict any problems that might prevent the deal from closing, to try and prevent them from happening and to take them into consideration when writing out goals. 


Aligning Your Sales and Marketing Efforts From the Get-Go

As a longtime leader of both sales and marketing teams, Whitney has seen the problems that can present themselves when these two efforts aren’t aligned. “Sales is looking for very big leads that they can turn into deals and close. They expect those leads to come from marketing,” she says, “But they generally have no idea what marketing really does. So, if they’re not getting the leads that they expect, the first thing they do is point fingers and blame marketing.”

Aside from this finger-pointing being destructive to the culture, she says, the results have a financial impact, as well. “If sales feels that they’re not getting enough leads out of marketing, they’ll spend money generating leads themselves,” says Whitney, “You end up spending a lot of money that you shouldn’t be spending.”

It’s important, therefore, that startup founders align their sales and marketing efforts as early as possible by determining the average number of leads it takes to close a deal. This will help to determine a single unified goal for both teams. 

Explaining her initial meeting with the VP of Marketing and Head of Sales at HelloSign, she says, “I sat them down in a room and said, ‘Alright, there’s one goal, one number. I don’t ever want to hear you two have separate numbers. If there’s a problem in the pipeline funnel, I don’t give a shit what side of the line it’s on because you both own it.’”

So, even if your startup is in its earliest stages and you’ve still got a lot of work to do before you hire sales and marketing teams, you want to get your pipeline in order now. If you can figure out who your customer is, how to reach them and how much it costs you to close each deal, you’ll find that expansion happens at a much faster rate. 

Christopher Zacher