GTM 23: Diversity

GTM 23: Diversity, Inclusion, and Sales Team Success

Today on the podcast, we have the privilege of speaking with Cara Felleman – a dynamic advisor, investor, and sales powerhouse. Cara is currently serving as the Vice President of Sales at Vividly and is also an LP at GTM Fund, where she uses her expertise to help startups grow and scale.

With a wealth of experience, Cara has a unique perspective on what it takes to succeed in a fast-paced and competitive environment. When it comes to hiring, she identifies two key attributes that she looks for in employees. The first is the unwavering drive to succeed despite obstacles. The second is having a positive outlook and being able to stay hopeful even when things seem hard.

Cara is also a passionate advocate for diversity and inclusion in the workplace. She believes that companies need to take into account the emotional and cultural impact of their decisions, such as layoffs, on employees.. Cara thinks we can make workplaces that are more fair and open to everyone if we approach these problems with empathy and understanding.

Join us as we delve into these important topics with Cara Felleman and gain valuable insights into what it takes to create fair, safe, and successful workplaces and sales teams.


(2:37) Qualities of a successful go-to-market professional

(5:46) Why companies need to be more considerate in layoffs 

(8:00) How layoffs have a greater impact on women

(11:50) Exploring strategies for attracting and retaining Gen Z talent

(16:24) Building the sales team at Resy: The challenges and lessons learned

(20:35) Finding the middle ground between control and collaboration

(32:19) Discussion on how to relinquish control and trust your sales team

(37:06) Conversation on radical candor 

(38:26) One thing most go-to-market leaders believe that is not true

(42:49) The value of human connection in business


“Working at an early-stage startup is about figuring out how to make lemonade out of a lemon that barely has juice in it.”

“If you are someone that looks at the negative, it’s going to be very difficult in this (early-stage startup) environment or when the market’s hot. You have to be able to say like I’m successful no matter what I have the will to do it. You have to be your best motivator.”

“There is a domino effect to women being laid off. Does that stop them from saying, ‘Well, do I have to choose my career or a family? If I choose to have a family, I’m more likely to be laid off because maybe I didn’t work a full year.’? That’s what they’re looking at. That really scares me.”

“The Gen Z market thinks very differently than what we’re used to. The Gen Z market absolutely will look down upon a company that does not have diversity. They want transparency.”

“If you have a side hustle, you’re gonna want a structure at work. If you do not have a side hustle, you’re going to want the flexibility in work. It really comes down to getting to know the individual and what they’re looking for. We can’t generalize that all Gen Z are this way, but it’s fair to say that by the time a Gen Z starts at a job, specifically a startup, you have to expect that they don’t have 5 years of work experience, but they have 5 years of work experience in different ways.”

“Gen Z is going to give us a run for our money and say, ‘Hey, you can continue doing this way. But I have an idea.’ And we should listen to those ideas because innovation is what’s going to keep us moving forward.”

“Your goal is to get to this incredible Island. When you get to the island, you win. Is that an exit? Is that going public? That boat ride is going to be rocky. But if you don’t all know why you’re on the boat and you’re not all paddling the same way, you’re not going to get to the island; you’re not going to win. So everyone needs to know how to win and why we’re making those decisions.”

“If you’re going from a Series A to Series B, one of the biggest things that investors look for is repeatability.”

“The best sellers are the ones that follow the process.”

“I strongly believe you should hire someone a little bit more expensive, that is more experienced, that can take on a larger remit, than to hire someone cheaper and younger to just do the job. Because that level of trust and expertise is there.”

“People do not care about the details of how the company came about, but when you’re a founder, they care to hear that from you.”

The GTM Podcast

Don’t miss The .GTM Podcast dropping every Tuesday, discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

And…monthly bonus podcast episodes dropping the first Thursday of every month.

Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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