Rich Toland

Trailblazer
DISC Type : DI

Large Enterprise Account Executive at Paylocity

New York City Metropolitan Area, United States

Overview

Rich Toland is a Large Enterprise Account Executive at Paylocity with over 20 years of experience focusing on enterprise HR and payroll solutions. A graduate of Rutgers University, he is described by colleagues as genuine, innovative, and a true connector who prioritizes client interests.

Rich has a strong interest in the intersection of sports and technology, demonstrated by a patent he co-holds. He values personal connection, often attending industry conferences and hosting client events, such as a recent Miami Heat basketball game, to build camaraderie with friends old and new.

He holds a U. S. patent for a method of providing digital athlete profiles, combining his interests in sports and tech.

Personality Overview

Informal

Achievement-Oriented

Friendly But Fast

They prefer to ensure that they are in control of the situation.  A combination of speed and relationship gets the best response from them. If they come to believe in your value proposition, they will be your champion.

Topics They Care About

Client-First Philosophy
Believes the client's best interests must come first, a core philosophy that guides his decision-making and business practices.
HR Technology
Specializes in modern HR and payroll solutions that automate administrative tasks and empower employee growth for large, complex organizations.
AI in HR
Shows a keen interest in the practical applications and ethical concerns of AI in human resources, sharing related research with his network.

Media Appearances

Comms vNext 2026 – Speaker: Richard Toland (Large Enterprise Account Executive, Paylocity). Featured in JustAttend (Comms vNext 2026)

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Comms vNext 2025 – Speaker: Richard Toland (Large Enterprise Account Executive, Paylocity). Featured in JustAttend (Comms vNext 2025)

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Work History

7-2025
Large Enterprise Account Executive at Paylocity
1-2025 - 7-2025
Vice President, Employee Benefits at USI Insurance Services
10-2023 - 1-2025
Business Consultant/VC Relationship Manager at Sequoia
10-2023 - 1-2025
Enterprise Business Consultant at Sequoia
2-2021 - 10-2023
Senior Enterprise Account Executive at BetterUp

Education

B.S. from Rutgers University
Education details unavailable from Middletown North High School

More Information

Social Presence :

Prographics :

Exp : 16 Location : New York City Metropolitan Area, United States Job Level : Mid-senior Designation : Large Enterprise Account Executive at Paylocity
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Insights For Selling To Rich

During A Call Or A Meeting

DO's

  • Showcase existing customers and use case-studies to grab their attention
  • Display high self-confidence and expect them to have a strong personality.
  • Build a trustworthy relationship while keeping the product center-stage

DONT's

  • Do not look like someone who doesn’t know what they are talking about
  • Don't make any commitments that you might not be able to fulfill
  • Don’t force involvement of other stakeholders unless it is critical

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Rich is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Rich

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Rich move?

  • If you earn their trust and they develop faith in the product, they can make decisions quickly.
  • Can Rich take some risk or not?

  • If necessary, they will be ready to take risks.

You And Rich

Personality Compatibility


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