Ryan Gallo

Pioneer
DISC Type : sid

Chief Sales Officer at Nava Benefits

Boston, Massachusetts, United States

Overview

Ryan is a seasoned revenue leader specializing in SaaS go-to-market strategy and team building. He has a history of driving significant growth, including scaling B2B revenue at Dashlane from \$4M to \$23. 5M and achieving record performance at Canto. Colleagues describe him as masterful, eloquent, and strategic.

As employee #38 at HubSpot, he built the outbound sales motion from the ground up, scaling it to \$11M in ARR.

Personality Overview

Friendly But Fast

Decisive But Friendly

Driven But Considerate

If they are convinced, they can become very strong champions for your product  They have the unique ability to win both love and respect from their team (or outsiders) They combine a unique set of diverse traits where they are fast and friendly but can slow down to be thorough when needed

Topics They Care About

SaaS GTM Strategy
Expert in building and resetting go-to-market structures to accelerate growth, as demonstrated in executive roles at Deel, Canto, and Dashlane.
Revenue Acceleration
Proven experience in leading rapid revenue turnarounds and scaling B2B revenue streams, significantly increasing company growth and profitability.
Sales Team Building
Passionate about building sales motions from scratch, having scaled HubSpot's outbound BDR team from its first member to a multi-million dollar ARR contributor.

Media Appearances

Ryan has no verified media appearances

Work History

1-2025
Chief Sales Officer at Nava Benefits
3-2024 - 1-2025
Chief Revenue Officer at Deel IT (Hofy acquired by deel)
7-2023 - 3-2024
Chief Revenue Officer at Canto at Canto
1-2020 - 7-2023
Vice President, B2B Revenue at Dashlane
1-2016 - 12-2019
VP Sales at HubSpot

Education

1999 - 2003
Politcal Science/History & English Minor from Union College
2003 - 2003
Education details unavailable from University of York

More Information

Social Presence :

Prographics :

Exp : 14 Location : Boston, Massachusetts, United States Job Level : Leadership Designation : Chief Sales Officer at Nava Benefits
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Insights For Selling To Ryan

During A Call Or A Meeting

DO's

  • Ask them for a lunch or coffee once some rapport has been established
  • Use phrases like ‘your decision will’, ‘you will impact’ etc.
  • During followups, use calls or text if needed, they should be fine

DONT's

  • Don’t be too verbose or overly friendly; a little bit, however, is fine
  • Avoid focusing only on the product or its ROI, keep building trust subtly
  • Don’t hesitate from asking questions or pushing them, but take a formal approach

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ryan is

  • Nothing less than a strong combination of proof of results, relationship and high levels of professionalism is effective with them.
  • Will you ever get a clear answer from Ryan

  • They can say no while staying friendly, but can also be pursuaded to reconsider

Insights For Deal Planning

    How fast (or slow) will Ryan move?

  • They are generally fast movers and can take quick decisions
  • Can Ryan take some risk or not?

  • They have high risk-appetite but can get ahead of themselves once in a while. Observe carefully

You And Ryan

Personality Compatibility


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