Sales Talk for CEOs: Gabriella DeFlorio on Being First to Market: How She Started Prelay (S5Ep12)

Dec 5, 2023 | Sales Talk for CEOs Podcast

Gabriella enjoyed working with technical and operationally focused people tackling complex problems. She always worked in a team to do sales but didn’t like the lack of transparency to the team members as the deal progressed. She saw a need for a team selling tool.

“I really didn’t have any other option than starting this business and seeing where I could go with it.”

The team selling space had a huge need and Gabriella DeFlorio of Prelay knew she had to fill that need. Even with all her Go To Market experience, it’s different when you start a category and Prelay did that.

She started small with some beta customers and about a year later she was really able to go sell.

Her Go To Market background made her know she should be on the frontlines. It allowed her to continue gathering information to shape the product.

“You can’t lose touch with the customers.” This keeps her close to her customers today, even though she has a sales team.

The first sellers she brought on covered the deals end to end and soon after she brought on customer success and a head of sales keeping herself in the game as the subject matter expert.

It was challenging to find the right people for an early stage company. Finding the right people who were ok with the ambiguity and who were utility players and product aware. ”Because of this we’re very focused on knowledge sharing.”

Her biggest challenge, becoming a “household name.” Gabriella is excited about having Prelay become a name in the market. She feels it is important to stay focused on awareness. “It’s a space that is just being created.. There’s no team selling product like Prelay.”

She stays involved on the product side and has directed her sellers to insert her where she is needed.

Listen to her tell the story of starting a company and a category and growing her sales.


[00:04] Selling is a team sport, lone wolf sellers are outdated.

[03:22] Gabriella’s background in scaling startups led to creating Prelay.

[10:54] Thoughtful R&D and user-centric approach in the beginning.

[13:04] The importance of CEOs staying close to the customer

[16:20] Challenges of scaling and growing the team

[22:30] CEO involvement in complex workflows and strategic deals

[23:49] Balancing involvement in deals with the sales team’s capabilities

[25:03] Discussing the growth of the SE organization

[26:17] Importance of in-person connections and LinkedIn presence

[27:36] Building an advisory council for networking and support

About Guest

In a past life, Gabriella was an Olympic Trials hopeful and a competitive D1 cross country & track athlete at the University of Michigan. During her competitive running career, 7 leg surgeries failed to keep her off the D1 stage, reinforcing her core approach to life – persistence and perseverance can lead you to achieve feats that may seem impossible at first.

Gabriella leveraged the same mindset when entering the tech industry, where she discovered a similar spark of excitement and passion in scaling companies. Taking on Silicon Valley, she helped scale core go-to-market at Fountain (YC W15) and at Truework (Sequoia-backed).

Now at Prelay, she is building the future of revenue team collaboration.

To learn more about Prelay, you can get in touch via gabriella (@)

Social Links

You can learn more about and connect with Gabriella DeFlorio in the links below.

Connect with Gabriella on LinkedIn:

(99+) Gabriella DeFlorio | LinkedIn

Check out Prelay’s website:

Prelay | Drive Revenue Faster as a Team

You can learn more about and connect with Alice Heiman in the links below.

Connect with Alice on LinkedIn:

(99+) Alice Heiman | LinkedIn

Check out Alice’s website:

Alice Heiman – Alice Heiman


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