Doug Bewsher of Leadspace on Marketing Cadence, Hires, Vision and Focus

May 26, 2016

Doug Bewsher’s professional experience has given him unique insight into what it takes to run and market software companies. He has led marketing for some of the best known (and most emulated) brands in the social and mobile spaces including and Skype. As CMO of the former, Bewsher launched Salesforce Communities and Chatterbox, which made critical contributions to the company’s incredible growth. In the same role at Skype, his efforts helped grow the company’s user base to an impressive 750 million. Now, as the CEO of Leadspace, Bewsher works with leading B2B brands like Microsoft, Oracle, RingCentral and SAP to transform their lead generation, applying the power of predictive analytics to Big Data to improve engagement, boost lead conversions and ultimately drive more pipeline.

Matching Marketing Cadence to Company Size

Bewsher’s first CMO role was with a company called mig33, a social gaming platform backed by Accel and Redpoint. From there, he was recruited to join Skype, and after that he stepped into the CMO position at Salesforce. With each transition, Bewsher’s team and budget scaled as the overall size of the company – from 50 people at migg33 to 1,000 at Skype to 10,000 at Salesforce – grew. One thing Bewsher noticed as he progressed to increasingly larger companies was the corresponding change in the cadence of operations.

“When you’re running marketing at a smaller company, you have to be a very hands-on operator,” Bewsher says. Describing his level of his involvement in day-to-day marketing tasks at mig33 he recalls, “I had to be very conversant in all the core growth marketing tactics, and I was literally doing things like changing landing page designs and editing lines on core content assets.”

In addition to having broad knowledge and hands-on expertise, Bewsher emphasizes the importance of agility and organizational skills in a CMO at a smaller company. “You have to be incredibly good at prioritization,” he says. “The most important difference for this size marketing team is the speed at which you have to consider things and make decisions.” The cadence of operation, Bewsher explains, is extremely fast, almost in real time. “If there was a marketing tactic I wanted to act on, I had to make the decision and act on it right away,” he recalls. “There’s no real long-term planning at a company this size. You think of something, get it done today, and move on to the next thing.”

At his subsequent positions at Skype and Salesforce, the cadence of marketing activity stretched to a month and then to three months, respectively. But, even with this slightly longer-term view, Bewsher says it’s always critical to complete tasks and keep the whole operation moving. He does note, however, that you have to work in a way that is suited to the size of the organization. “That cadence of thinking about the timeline and how you operate is very important,” he says. “A marketing person from a larger company may have an awesome skill set and really know what they’re doing, but if they’re used to building quarterly plans and try to use that same approach in a smaller company, it just doesn’t work.”

While at Salesforce, Bewsher worked closely with the company’s CEO, Marc Benioff. “I learned many things from Marc,” Bewsher says. “He always said that tactics dictate strategy. So, for instance, if you’re a marketer in a smaller company you need to think about your plan in terms of getting things done. This might mean moving quickly in the right direction using agile marketing rather than building a big, long-term plan and then a waterfall. The tactics you use dictate the larger strategy. It’s an interesting concept.”

Something else Bewsher recognized is the distinct differences in the CMO role depending on the size of the company. Smaller companies, Bewsher points out, don’t have CMOs, they have VPs of Marketing. “Even though we tend to give everyone at a startup a C-title, for me a CMO’s role is really about the coordination of multiple stakeholders, product lines, and marketing programs into a cohesive whole,” he explains. “Whereas the role of a VP of Marketing is simply to deliver brilliant marketing and take day-to-day ownership of marketing tasks.” These two different roles require very different skill sets, so understanding which one you actually need is important for successful hiring.

Deciding When to Make Certain Key Hires

Building a great team is one of a leader’s most important responsibilities. It can also be one of the most challenging, particularly for the CEOs of expansion stage software companies who have to make a lot of strategic decisions about how and when to bring in certain players.

For instance, there’s a lot of conversation in the SaaS industry right now about how to balance marketing and customer success. Which role should be given priority? When is the right time to hire a CMO or a VP of Customer Success? Bewsher has some strong opinions on the topic. “In general, I think that the CMO is one of the last roles you need to fill on your management team,” he says. “A lot of companies hire a CMO too early when all they really need is a director of marketing. The time to hire a CMO is when the company is big enough that you’re doing lots of events and evangelizing, and then you need to hire a sufficiently senior person who can handle that stage of growth. Though there are always exceptions, I completely buy that customer success needs to happen before you focus on generating more marketing leads.”

“The question you need to ask is what does a VP of customer success really look like, and what does this person do,” Bewsher says. “I joined Skype because most of the company’s growth comes from viral word of mouth. Salesforce grows in the same way – people like the product. And I joined Leadspace for the same reason. I believe that most of our growth is coming from referrals. That’s customer success.”

As with many other linchpin decisions, the hiring question comes down to a matter of timing. “Operationalized customer success is a sophisticated process,” Bewsher explains. “If you hire a VP of customer success too early – like when you’ve only got three customers – you’re only filling a very generalized kind of account management role. So, while it’s important to have somebody who can ensure customer success, the job description will be different depending on how many customers you have.”

Building Around a Vision

Bewsher also has some actionable advice for early stage CEOs. “When I was starting out, somebody told me that the three core things you do as a CEO are set a vision, make sure there’s money in the bank, and hire great people,” he says. If pressed, however, Bewsher adds that the one thing the CEO needs to focus on is product market fit.

“Your product market fit is, in a sense, your vision,” he explains. “And, you have to have that vision. Vision is what separates brilliant entrepreneur CEOs from others – they have an idea and they know where they’re going.” Bewsher is a strong believer that you either have that vision from the start, or you don’t. “A vision usually starts with a story,” he says. “It’s a bit like when I was at Salesforce. Three days into my job as CMO, I looked at the challenges of lead generation for complex B2B sales cycles and said, ‘Somebody needs to solve this problem.’ A year later I left to run a company that is solving that very problem.”

On the topic of building a great team, Bewsher says he looks for fellow evangelists who “get” the vision and embrace it. “The first thing I look for when I’m hiring is whether the candidate really believes in what we’re trying to do,” he says. “At the end of the day, if they don’t believe in where we’re going – not based on facts, but in their gut – we shouldn’t be hiring them.”

Getting Back to the Basics

Whether you’re a CEO, CMO, VP of marketing or director of customer success, Bewsher believes that marketing is evolving to a state where all efforts align around product market fit. “What we’re seeing is a shift back to the core of marketing, which is customer insight,” he says. “For a while, we had growth hackers and marketing became focused on how to get the product into people’s hands. But, that’s changed. Now it’s more about understanding the customer, figuring out their needs, and building a really great product that solves for those needs. That’s what really matters when you’ve got so much competition.”

Bewsher is excited by this shift. “While a lot of the cool companies of the 90s were founded by product guys, now that we have resources like Amazon Web Services and Leadspace finding people and building your products in the cloud, all of a sudden it’s actually become quite easy to build products again. So, the magic of the guys who can build a product is much less important than getting the right product market fit. Marketing is back on top, and I think the role will continue to evolve and become more important.”