Ryan Gallo in

Ryan Gallo

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Chief Sales Officer at Nava Benefits
📍 Boston, Massachusetts, United States

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.

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Experience
14 Years
Current Role
Chief Sales Officer
Job Level
Leadership
Location
Boston, Massachusetts, United States
Personality Overview

How Ryan shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Ryan cares 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.
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Career

Work history

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

Media appearances

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Education
1999 - 2003
Politcal Science/History & English Minor
Union College
2003 - 2003
Education details unavailable
University of York
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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