How to Inject Discomfort Into Your Scale Journey
Play • 36 min

Cynthia Gumbert is the CMO of SmartBear, the ~750-person PE-backed SaaS company that is on a growth tear, serving more and more software developers every day.

Cynthia reflects on her transition from VP of Marketing to CMO. We discuss the difference between a marketing-centric mindset and a 'business first, marketing second' mindset. It's this 'business first' mindset that is key for a CMO in scaling mode. That mindset entails putting yourself into the CEO's shoes and thinking about how to help the whole company grow, not just how to grow marketing's results. In other words, change your frame from 'what marketing is doing' to 'what the company is doing.'

A big part of scaling is creating discomfort with the status quo. You'll hear these learnings:

  • Expect to hit plateaus as you scale. When you do, ask, “How do we double doing well here?”
  • Hire for 'cultural add' as opposed to 'cultural fit' as you scale… even when that involves overcoming some discomfort.
  • Look for ways to organize to reflect the full arc of the customer experience. In Cynthia's case, she expanded the marketing org to include communities and the training academy, as part of one web and digital experience team. This led to a 400% increase in academy enrollments.

Cynthia also touched on an interesting trend for 2022: the need for micro market research. With product-led growth, customers will follow the journey of website --> trial → product. Marketers must be hyper-aware of micro customer segments and the messages that will help customers accomplish their specific goals.



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Hiring great marketing leaders is not easy. The Get is a podcast designed to inspire smart decisions around recruiting and leadership in B2B SaaS marketing. 

We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is Solving for the Scale Journey.

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at You can also follow Erica on LinkedIn, or sign up for her newsletter at

The Get is produced by Evo Terra and Simpler Media Productions.

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