Wil B.

Enigma
DISC Type : idc

Proprietor, Schedulefly at Schedulefly

Waxhaw, North Carolina, United States

Overview

Wil is a seasoned entrepreneur dedicated to the hospitality industry. After co-founding and successfully selling the startup First Research to D&B, he founded Schedulefly to serve independent restaurants. He holds a Bachelor of Arts from Davidson College and leads his current venture with a small, passionate team.

He hosts the "Restaurant Owners Uncorked" podcast, where he shares the unique stories of industry leaders and celebrates their journeys. This passion for storytelling stems from a deep respect for the people behind the businesses he serves. In his personal time, Wil enjoys life on his farm.

Unique fact: Wil runs his technology company using a flip phone, a detail he proudly includes in his professional headline.

Personality Overview

Fast Follower

Persuasive & Assertive

Hard To Convince

They can sound friendly and charming but can quickly change gears to become inquisitive and probing  They are generally strong communicators and are not easy to convince. They are likely to ask many questions and look heavily for supporting proof as well as information.

Topics They Care About

Independent Restaurants
Founded Schedulefly to serve independent restaurants, bars, and coffee shops, expressing deep respect for them as the lifeblood of local culture and community.
Entrepreneurial Stories
Hosts the "Restaurant Owners Uncorked" podcast to share the unique and inspiring journeys of hospitality entrepreneurs, celebrating their passion and dedication.
Startup Growth
Successfully co-founded and exited his first startup, First Research. He now leads a small, dedicated team at Schedulefly, focusing on sustainable growth and customer relationships.

Media Appearances

1010: Wil Brawley – Podcast Host, Author, and Co‑Owner of Schedulefly. Featured in Spotify

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Wil Brawley of Schedulefly – Digital Hospitality. Featured in Apple Podcasts

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Meet Wil Brawley — The Guy Who Built Schedulefly. Featured in YouTube Shorts

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Work History

10-2008
Proprietor, Schedulefly at Schedulefly
3-2000 - 6-2008
Co-Founder at First Research
8-1996 - 2-2000
AVP, Treasury Management Officer at Bank of America

Education

9-1992 - 5-1996
Bachelor of Arts - BA from Davidson College
9-1994 - 12-1994
Semester Abroad from Florida State University

More Information

Social Presence :

Prographics :

Exp : N/A Location : Waxhaw, North Carolina, United States Job Level : N/A Designation : Proprietor, Schedulefly at Schedulefly
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Insights For Selling To Wil

During A Call Or A Meeting

DO's

  • Leverage 'negging', or the art of asking negative questions like "you must not be convinced yet..."
  • Use a combination of data as well as stories for your pitch, a ppt might not be necessary
  • Build rapport slwly without rushing, it will come handy to handle hard questions later

DONT's

  • Avoid long presentations and just 'high-level' value proposition, dive into the details
  • Avoid making offhand commitments, understand the root of their concerns first
  • Don’t brush off any concerns, take all questions seriously. They are easily deterred

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Wil is

  • Proven value, strong objective evidence are important for them, rapport can impact decisions a little.
  • Will you ever get a clear answer from Wil

  • They are practical and friendly, but can give a clear response with a little prodding

Insights For Deal Planning

    How fast (or slow) will Wil move?

  • They like to be detailed, so unless they develop strong conviction, they can take their time to arrive at decisions
  • Can Wil take some risk or not?

  • They evaluate their decisions systematically and do not take risks that often, unless you can get them to develop strong conviction

You And Wil

Personality Compatibility


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