Kyle Racki

Co-Founder and CEO, Proposify
Dartmouth, Nova Scotia,Canada
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Who Is Kyle Racki?

Total Experience26 years
CompanyProposify
CountryCanada

Kyle Racki is a well-known entrepreneur, author, and speaker, primarily recognized as the Co-founder and CEO of Proposify, a leading SaaS company that helps businesses create, send, track, and e-sign proposals, quotes, and contracts. With a background in design and marketing, Kyle identified a significant pain point in the sales proposal process and co-founded Proposify in 2013 to solve it. He is known for his transparency in sharing the ups and downs of his entrepreneurial journey, often discussing topics like bootstrapping (though Proposify later took funding), product-led growth, company culture, and the realities of building a SaaS business. Kyle is passionate about helping sales and marketing teams improve their processes and close more deals.

How Did Kyle Racki's Career Path Shape Their Journey?

Kyle Racki's work history includes a series of influential roles in various companies. Here is a detailed list of his professional journey:

Proposify - Co-Founder and CEO(2014 to Present)
Bright - Director Board Of Directors(2021 to 2023)
SaaS Academy - Boardroom Coach(2021 to 2023)
Headspace Design - Principal, Design Director(2008 to 2014)
NSCC - Web Design Instructor(2011 to 2011)
Modern Media - Lead Interactive Designer(2007 to 2008)
Impact Communications - Senior Designer(2004 to 2007)
Transcontinental Specialty Publications and Holiday Media - Designer(2003 to 2004)

What Are Kyle Racki's Key Achievements?

Co-founder and CEO of Proposify

Successfully co-founded and scaled Proposify from an idea into a globally recognized online proposal software, serving thousands of customers and helping them streamline their sales document workflow and increase close rates.

Author of 'Free Trials (and Tribulations)'

Authored the book 'Free Trials (and Tribulations): How To Build A Business While Getting Punched In The Mouth,' sharing candid insights and lessons learned from his entrepreneurial journey in building Proposify.

Secured Significant Venture Capital Funding

Led Proposify to secure significant funding rounds, including a notable Series A round led by Susquehanna Growth Equity, enabling further product development and market expansion.

Recognized SaaS Thought Leader and Speaker

Frequently invited to speak at industry conferences and podcasts, sharing his expertise on SaaS, entrepreneurship, sales processes, and marketing. He actively contributes to the SaaS community through his writings and talks.

Built a Strong Company Culture

Focused on creating a positive and productive work environment at Proposify, emphasizing employee well-being and growth, which has contributed to the company's success and talent retention.

What's Kyle Racki's Educational Background?

Diploma, Graphic Design

Nova Scotia Community College - Year 2001

Degree Program

Auburn High - Year 1998

Buying Intent Signals for Kyle Racki

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Notable news
Hiring actively
Corporate Finance
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Corporate Finance

Company Overview

Proposify
Total employees185
HeadquartersHalifax
Founded2013

Proposify is a cloud-based proposal software that helps modern sales teams create, send, track, and e-sign winning proposals, quotes, and contracts. It streamlines the proposal process, enabling sales reps to close deals faster by providing them with tools for consistency, control, and visibility into their sales pipeline. Key features include a content library, design templates, real-time notifications, electronic signatures, and integrations with popular CRM and sales tools.

Proposify Funding Information
Unknown - Total Funding Raised
$10M - Most recent funding amount
4 - Number of funding rounds
19 Jan, 2022 - Latest funding round
Lead Investors:
Canadian Business Growth Fund (CBGF)
Build Ventures
Innovacorp
East Valley Ventures

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