Rick Milley, CPA, MBA in

Rick Milley, CPA, MBA

Evaluator · DISC type csd
Senior Regional Director, Enterprise at ClickUp
📍 Boston, Massachusetts, United States

Professional overview including current role context, leadership scope, domain focus, and career trajectory to help you understand background relevance before outreach.

Key behavioral and communication insights including interaction style, decision-making tendencies, and motivation drivers to tailor messaging and personalize conversations.

Business priorities, areas of interest, and practical outreach recommendations that can improve conversion quality for this professional.

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Experience
7 Years
Current Role
Senior Regional Director, Enterprise
Job Level
Senior
Location
Boston, Massachusetts, United States
Personality Overview

How Rick shows up

Fast But Analytical
Hard To Convince
Quality Focused

They focus on the results, but can still be quite procedural and analytical about how to get there They have a unique set of diverse traits where they are decisive and methodical but can sometimes be extra cautious and skeptical They are not very likely to become strong advocates of your product or service

Priorities

Topics Rick cares about

Strategic Priorities
Topic insights and context to help personalize outreach and discovery conversations.
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Career

Work history

3-2026
Senior Regional Director, Enterprise
ClickUp
4-2025 - 3-2026
Senior Regional Director, Large Enterprise
Smartsheet
5-2024 - 4-2025
Regional Director, Large Enterprise
Smartsheet
5-2023 - 5-2024
Regional Director, New Business | Enterprise
Smartsheet
3-2016 - 4-2017
Account Executive
NetSuite
In the press

Media appearances

Media appearances and press coverage highlighting public visibility and thought leadership.
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Education
2010 - 2012
Master of Business Administration (MBA)
Bentley University - McCallum Graduate School of Business
2008 - 2010
Bachelor's Degree
Bentley University
Social presence
in
Behavioral profile

DISC profile (public)

c

Calculativeness (C)

Calculativeness (C) reflects the degree to which a person is likely to be cautious, systematic and analytical. Those scoring high tend to emphasise quality and accuracy.

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