Raianne Reiss

Caretaker
DISC Type : Si

Chief Marketing Officer at Skillsoft

Greater Chicago Area, United States

Overview

Raianne Reiss is the Chief Marketing Officer at Skillsoft, with over 20 years of experience leading marketing for global brands like Yext and Amazon Web Services. She holds a BS from Northern Illinois University. Colleagues describe her as creative, focused, and a top-notch marketing professional with expertise in go-to-market strategy.

She is passionate about the power of technology to drive transformation and the art of powerful storytelling. Her commitment to unlocking human potential through continuous learning aligns directly with her leadership role at Skillsoft, a mission she finds deeply resonant.

She was instrumental in Yexts acquisition of Hearsay Systems, creating the industrys first end-to-end digital presence platform.

Personality Overview

Nice But Slow

Supportive

Collaborative

They are more likely to go for proven solutions.  Win-win scenarios can appeal strongly to them. Unlike D or C types, they are calm as well as friendly and can give the impression of being more receptive than they actually are.

Topics They Care About

AI in Marketing
Believes marketers must evolve beyond traditional SEO to creating high-quality, relevant content to succeed in an AI-powered world.
Continuous Learning
Passionate about unlocking human potential through learning, a core mission of her current company, Skillsoft, which she has expressed great excitement for.
Digital Presence
Recently helped lead the acquisition of Hearsay Systems by Yext to create a complete, end-to-end digital presence platform for businesses.

Media Appearances

Skillsoft Appoints Raianne Reiss as Chief Marketing Officer. Featured in Skillsoft Investor Relations (press release)

See Now

Work History

4-2025
Chief Marketing Officer at Skillsoft
8-2022 - 4-2025
EVP and Chief Marketing Officer at Yext
4-2021 - 8-2022
Vice President, Marketing at Elastic
3-2020 - 4-2021
Head of Americas Marketing at Amazon Web Services (AWS)
5-2019 - 3-2020
Head of US Marketing at Amazon Web Services (AWS)

Education

BS from Northern Illinois University

More Information

Social Presence :

Prographics :

Exp : 25 Location : Greater Chicago Area, United States Job Level : Leadership Designation : Chief Marketing Officer at Skillsoft

Interested in

Lifestyle

Storytelling

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Insights For Selling To Raianne

During A Call Or A Meeting

DO's

  • Take time to make them feel comfortable before getting to the main pitch
  • Use phrases like ‘trust me when’, ‘your team will love’ etc.
  • If possible, involve their colleagues in the sales process

DONT's

  • Don’t push them to make decisions very fast, let them take their time
  • Avoid unnecessary confrontation if it arises incidentally
  • Don’t sound very transactional

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Raianne is

  • Relationships can sway their decisions, followed by the low risk and the presence of good evidence.
  • Will you ever get a clear answer from Raianne

  • They are diplomatic when needed and rarely say no directly.

Insights For Deal Planning

    How fast (or slow) will Raianne move?

  • Even if they are engaged and friendly, they can take their time to make decisions.
  • Can Raianne take some risk or not?

  • They probably won’t put a lot at risk.

You And Raianne

Personality Compatibility


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